(2) Al Capone’s MOST FEARED Hitman: The Story of Machine Gun Jack McGurn | FULL DOCUMENTARY

At 10:30 on the morning of February the 14th, 1929, as snow fell quietly over North Clark Street in Chicago, the stillness was shattered by the deafening chatter of machine guns and the booming blasts of shotguns. The echoes ricocheted off the brick buildings, sending neighbors rushing to their windows.

 To many, the shots seemed to come from the SMC Cartage Company at 2122 North Clark Street, a plain brick garage that in an instant had become the center of a battlefield. Some even swore that they saw a police car speeding away only moments after the gunfire stopped. When officers arrived at the garage 10 minutes later, they were confronted with a sight that would horrify the nation.

Inside the garage, seven men laid dead. All prominent members of Chicago’s Northside gang. They had been lined up against a wall by what they thought were policemen and executed with cold precision. In truth, the policemen were disguised members of Al Capone Chicago outfits and the killings would soon be immortalized as the St.

 Valentine’s Day massacre, effectively ending a bloody 5-year turf war between Al Capone’s crew and their bitter rivals, the North Side Gang. For Capone, it was a decisive victory. But the man who brought it to life was not Capone himself. It was his most trusted killer. In the garage that morning, he stood behind a Thompson submachine gun, the so-called Chicago typewriter, and cut loose on the helpless Northside men.

Each burst of fire cemented the reputation that already haunted Chicago’s underworld and gave way to the name that would follow him forever, Machine Gun Jack McGern. By the time of the massacre, McGurn had already killed 25 rivals of the Chicago outfits and seven would be assassins of his boss, Al Capone.

 He had nearly beaten comedian Joe E. Lewis to death for refusing to perform at a Capone controlled nightclub, and he had become the outfit’s most reliable enforcer in an era when Chicago itself was drowning in blood during the roaring 20s. This is the story of McGurn’s rise from small-time boxer to Capone’s deadliest hitman, of the bloody Prohibition years when Chicago was quite literally a battlefield, and of the inevitable downfall that awaited him.

 This is the untold story of Al Capone’s most feared hitman, Machine Gun Jack McGern. Machine gun Jack McGurn was born Vincenzo Antonio Jabaldi on the 2nd of July 1902 in the Sicilian port town of Leicarta on the island’s south coast. He was the first child of newlyweds Juspinia and Tomaso Jabaldi’s four children. And let’s do a little math to really hone down on how different these times were.

Josephine would have been just 13 when she married to Maro, who was 25 years old when they tied the knot in 1901, and she had Jack a year later at the age of 14. The idea of such a significant age gap and Jeppina’s incredibly young age might sound like a rather uncomfortable reality today, but really it wasn’t all that uncommon back then.

 Shortly after Jack’s birth, Tomaso immigrated to the US, hoping to bring his wife and son over the ocean as soon as he’d settled in. This era was called the Great Arrival, and it was when many men looked west to America in search of a better life for their families and more opportunities. Given Italy’s economic troubles after its unification, it shouldn’t be surprising that so many Italians boarded the boat seeking better wages, more sustainable farmland, and an actual opportunity to become wealthy based not on a person’s lineage of

birth, but only on their skills and an individual’s hunger for success. But there were other countries that saw enormous chunks of their population leaving for the land of opportunity too. Ireland, Canada, Australia, most countries in South America, and many Jews left Europe to get away from their centuries long alienation in the countries where they lived.

 The men came first. They found laborious jobs on the docks, the agricultural fields, or anywhere that would have them so that they could send money back home with the eventual plan to bring their wives and children to their new home in just a few years. The kids that came after or that were born on US soil were no longer just Italians or Jews or whatever country their parents came from.

 They were now Americans going to school, playing in the fields, and living next to people from nearly every corner of the earth. And when times are tough, neighborhood kids stick together, no matter what language you spoke or how purebred your parents were. This is the world that 4-year-old Jack came to settle in. Juspena was 18 when she embarked on a ship called the Gregory Morch from Polmo port, later renamed to the SS Muhen and sunk by a Soviet submarine in World War II.

 On November the 24th, 1906, Jack and his mother arrived at Ellis Island, the largest immigrant and inspection station in the United States. Upon arrival, they went through the rigorous and uncomfortable medical examinations to receive their papers that allowed them into the country. They joined to Marso and settled in Red Hook, Brooklyn, where Jack went to public school number 46 located on 100 Claremont Avenue, Brooklyn for the next 11 years.

 In that time, Jeppina and Tomaso had three more children, and the family Americanized their names. Many Italian families adopted this habit to better fit in, and so that their children would not feel so alienated from their neighbors. Josephina started going by Josephine, Tomo became Tommy, and Vincenzo was dropped in favor of Vincent.

 The name Jack, the notorious killer title that the press and the nation would come to associate him with would come later. But for now, it’ just be easier to refer to him as Jack since that’s the name that he would become known for. So Jack’s siblings arrived almost as soon as they touched down in the new world.

 Salvator was born at the end of their first year in the US in December 1906 and he went by the name Sam. An Francesco went by Frank and he was born in 1910. And finally came Angelene who shortened her name to Angie and she was the last Jabaldi sister to arrive in 1912. Despite having four young children and a wife at home, Tomarso was rarely present.

 Like so many newly arrived Italian immigrants, he found work as a Steve Door on the Brooklyn docks. But as the years passed, he spent more and more of his time in the saloons of Bensonhurst and Sheep’s Head Bay, choosing drink and company after work over his family. By 1913, Josephine had endured enough and she left him. Josephine got married again relatively quickly to a local grosser named Angelo Deorei, of whom no photographs have survived of.

 Jack spoke very highly of his stepfather, and it’s clear that he loved Angelo very much. He certainly saw him more often than he’d seen his own father in living memory. Angelo and Josephine would have five children in the next nine years. But while their family grew, life in Brooklyn was becoming increasingly difficult for Italian immigrants.

 Two gangs were locked in a bitter struggle for control of the Brooklyn docks. On one side stood Frankie Yale and his so-called Black Hand Gang, a name commonly used at the time for Italian extortion rackets that prayed on their own communities. Opposing them was the Irish white-hand gang led by the volatile Wild Bill Love It.

 The docks were a gold mine and whoever controlled them controlled Brooklyn. For Angelo Deorei, the constant tension between the Italians and the Irish was too much. Though he earned a respectable living as a grosser, the Black Hand demanded weekly payments from him to support their war against the Irish. Under mounting pressure and fearing for his family’s safety, Angelo made the decision to leave Brooklyn behind, he packed up his new wife and the nine children they were now raising and set his sights westward to Chicago. At this point in 1916, Jack

was just 14 and by all accounts absolutely devastated to leave his schoolmates behind. He was a gifted athlete, excelling in nearly every sport, which had made him popular amongst his peers. The thought of beginning again in a new city was daunting, but as the eldest, he understood it was the best chance for his younger brothers and sisters.

 When Deori moved his family to Chicago, however, Jack soon discovered that these streets were even harder around the edges than back in New York. They settled at the now demolished 622 South Morgan Street in Chicago’s Little Italy, thinking that they’d be safer in a new city if they were surrounded by their fellow Italians.

 Angelo continued his trade as a grosser, opening up his store at the corner of Blue Island Avenue and South Morgan Street, a short walk from his house, but sadly also a building that has now been demolished like a lot of Little Italy. But their presumption that they’d be safer surrounded by other Italians was a false one.

 Here they came to realize that Little Italy was controlled by another Blackhand extortionist gang, the Terrible Jenners, who also prayed on their own. They had a ruthless reputation. But Angelo was resolute. And when the inevitable knock came for the weekly tribute, he explained he hadn’t paid it in Brooklyn and he wasn’t going to pay it here.

 Deorei was tough and the Jenners backed off. However, Jack was soon experiencing the same pressure as Dei. Jack was no stranger to violence in Brooklyn because playground bustups and street brawls were common where he was from. However, in Chicago, the kids were quicker with their knives than they were back in Red Hook, and they smelled a newcomer a mile away.

 Getting away with his fast legs wasn’t enough anymore. Jack needed to learn how to defend himself properly, so he went to the local gym and learned how to use his fists, taking up boxing. here. His rather small stature, standing at just 5’5, was an advantage, making him quicker in the dodge and the punch than opponents that were twice his size.

Through that gym, he was offered a job as a caddy, where he predictably was a natural with a golf club. He was seen at the Evergreen Golf Course located on 91st Street and Western Avenue almost every weekend. Soon he wasn’t just playing and carrying around clubs for fat country club snobs. He was teaching younger kids too.

 With money from those lessons and tips from the caddying, Jack always had a little cash to carry around, not to mention a baby face that had the school girls swooning. He attended Goodrich High School on Taylor Street in the heart of Little Italy, but by this time he wasn’t the greatest student, mainly because his attention was at the gym.

 Jack was an exceptional boxer, one of the best in Illinois in his age group. Whilst Jack was making a name for himself in the ring, his mother received word from Brooklyn. Tomo Jabaldi, her ex-husband and Jack’s biological father, had been gunned down in a barbershop by Wild Bill Love, the ruthless leader of the Irish Whitehanders, in a case of mistaken identity.

 Jack, however, was completely unfased. He had little affection for Tomaso, and it was Angelo who he regarded as his true father. In truth, the loss had little impact on him, and he just continued to pour his energy entirely into his boxing career. After 2 years of spending more time in the gym than in school, Jack dropped out of high school at the age of 16 to focus full-time on his boxing career.

 And after learning of the death of his biological father, he dropped the name Vincent Jabaldi forever. Back then, boxing was a huge sport among Irishameans. Their clubs, gyms, and events had the most public support and were the most well-run compared to the Jewish and the Italian gyms. His chances of getting booked for fights if he had an Irish name was infinitely higher than any other ethnicity, so this decision was a career move.

 Besides, he was never too attached to his biological father’s last name. Anyway, he chose the dramatic moniker, Battling Jack McGurn, and it worked like a charm. He wouldn’t get booked for any broadcast fights until he turned 18. But these extra minor bookings had him running around the underground scene, building up a name for himself until he became a legal adult.

 Since he earned nothing from his fights as a teenager, Jack continued to pick up work as a caddy wherever he could and found steady labor on the Chicago docks, unintentionally following in the footsteps of his late father, Tom Maro. The day and seasonal shifts on the docks paid better than permanent jobs, and more importantly, it gave him the flexibility to devote hours to the gym.

On the waterfront, Jack earned a reputation as a reliable worker, often volunteering for the toughest assignments, hauling timber, unloading cargo, and shoveling coal. The grueling labor on the docks built him up quickly. The skinny boy of knobbybly knees and sharp elbows was soon transformed into a broadshouldered young man, his physique likened to that of a Greek god.

 At this stage in his life, there was no indication of what Jack would one day become. He was aware of the criminal world around him. In Chicago, the gangsters were hard to miss. Operating almost in the open. Boxing and crime often over overlapped, and it would have been impossible for Jack not to noticed the mobsters who lingered around the gyms and the fight halls.

 Yet, his focus remained totally fixed on the ring. Whatever interest the underworld may have had in him, Jack showed no inclination to be drawn in. The gangsters circling like vultures seemed to recognize this. For the time being, they let him be, content to wish him well and to leave him to his business. In September 1921, Jack got his first official fight as an adult.

 It was against an experienced boxer called Jim Ford, and Jack won. He won the next fight in November against Battling Williams 2. These first two fights were fought on the USS Commodore, a landlocked training ship which was docked at the Chicago Harbor. The Navy organized these matches between up and cominging fighters that didn’t need to be paid money to fight yet to boost soldier morale.

 And Jack was quickly becoming a favorite. When word of his wins made their rounds, the invitations for club and arena matches started rolling in. Naturally, these venues that didn’t have naval oversight were a hotbed for mob-based betting, and the babyfaced man of muscle was a sure thing to bet on. They called Jack the local 147 pounder from the west side.

 During the early years of the prohibition era when the sale, production, and transportation of alcohol was against the law, gangland Chicago was a fragmented landscape with three main gangs controlling the supply of illegal booze. The aforementioned terrible Jenners controlled Little Italy where they had over a thousand stills brewing gut rock moonshine.

 The Irish northsiders were led by Dinio Banyan and they controlled the north side of the city focusing on premium whiskey and beer. But undoubtedly the most powerful gang was the Italian southsiders who as the name suggests controlled the south side of the city and they were led by Johnny Torio and his protetéé Al Capone.

Al Capone was a man that Jack took to almost immediately. Only 3 years older, Capone was already a success. And like Jack, he had hailed from Brooklyn. He had fought in the bloody battle for control of the docks, the same conflict in which Jack’s father had been killed. By the age of 20, Capone had already killed four members of the Irish White Hand gang.

 But in 1919, federal agents were closing in on him for those murders. Not to mention the bloodthirsty wild Bill Love It had marked him for death and Capone was forced west to Chicago where he teamed up with Johnny Torio. By 1921, he was Toriel’s right-hand man and already a millionaire several times over with wages on Jack’s fights only adding to his fortune.

Toriel and Capone were often present at Jack’s bouts, and on more than one occasion, they congratulated him in person after another victory. A typical fight carried a $20 buyin, with the purse reaching around $300, nearly a year’s rent for a modest Brooklyn apartment at the time, or the equivalent of $7,000 today.

 And the Southside duo often won that purse. So, Capone made sure to congratulate Jack after every winning match because he was usually in on the bet. To call them acquaintances would be stretching the truth too far, but they were on speaking terms with each other from afar, at least enough for Jack to notice that there was infinitely more cash flowing between hands when the winners sat down for drinks after the match.

 And he also noticed the boxes of whiskey and cigars that were being loaded into a truck out back. These business dealings made their $300 that they won on Jack’s fight look like pocket change. And Capone didn’t hide his wealth. He wore tailored suits with a bright tie to add some flare. He always had pretty girls in the background. Capone could afford it.

 He made a cool million in that first year of prohibition. That’s a whopping $60 million today. And that’s just the cut that Capone got to second in command. Overall, the Southsiders made somewhere along the lines of $100 million in profits that year, and Jack was well aware of this. For now, though, he kept himself busy with his two jobs and rising career as a legitimate boxer.

However, his stepfather was having troubles that Jack wasn’t quite aware of just yet. Angelo Deore’s grocery store was once again targeted by the terrible Jenners, but this time they had absolutely no intention of backing off. By the end of 1921, the Jenner brothers had outmuscled every other gang in Little Italy.

 Their ranks bolstered by their huge profits in the first 2 years of prohibition. The Jenners were six Sicilian brothers hailing from Msala in Sicily about a 100 miles west of Leicarta, which is where Jack was born. They were led by the two youngest brothers, Bloody Angelo and Mike the Devil. These were the two most feared men in Little Italy and truth be told, probably the most feared men in Chicago, both being absolute specialists of violence.

 They didn’t import whiskey from Canada like the Southsiders or have huge breweries like the Northsiders. They had seen these breweries raided by prohibition agents and trucks hijacked from rival gangs and understood the risk of operating large centralized distilleries. So they devised a decentralized system. In typical Blackhand fashion, they forced newly arrived Italian immigrants to operate homemade stills in individual tenement apartments, minimizing the damage a police raid could cause to their overall operation. Many of these makeshift

stills were death traps. Accidents were common with explosions sending metal shrapnel and fire through packed tenement buildings. Deaths were common. Yet some workers still took the job willingly, lured by the promise of $15 a day, around $250 today, a fortune compared to honest labor. The lifeblood of these stills was sugar.

 Their moonshine operations ran on cheap, high yield alcohol, and sugar was the key ingredient. At the height of Prohibition, the six brothers controlled more than a thousand stills across Little Italy. each one needing a constant supply to keep production flowing. With sugar, they could turn out thousands of gallons of raw liquor every week, feeding Chicago’s insatiable demand for drink.

 And thus, every grosser in Little Italy had to order huge quantities of sugar from wholesalers, which wouldn’t raise eyebrows and sell it to them at a discounted price. Again, Deorei wasn’t having any of it. And I don’t think you can blame him. Of the nine children that he was responsible for, only two had moved out of the house, and a man doesn’t keep a house of a dozen fed, watered, and loved if he’s a pushover.

He told them to shove their sugar where the sun doesn’t shine, just like last time. To be honest, Deorei probably didn’t even have the money anyway because the family weren’t exactly rolling in the dough after all. But a few days after this, the terrible Jenners sent three of their own men over to the shop.

 And sadly, Angelo Deorei was shot dead on January the 8th, 1923. Jack was utterly devastated. He’d never had much pride in his constantly changing names or his surname. He never cared or thought about his biological father, but there was one thing that he was always certain of. Angelo Deorei was his father in all the ways that counted.

He treated every child the same. He loved his wife to distraction, and he supported all of his children, no matter what their dreams were. Not only had Jack lost his father, he was just 21 years old when Angelo was killed and now the head of a household of 11. His mother, Josephine, was pregnant at the time, and the shock of hearing of her husband’s death caused her to miscarry.

The baby and Angelo Deorei were buried together at Mount Carmel Cemetery in Hillside, Illinois. Jack was drowning in grief, and that sorrow soon hardened into rage. At that moment, he swore an oath to himself. He would find the three men responsible for Angelo Deore’s death, and he would kill them.

 It was no empty vow. For the first time, the mask of the babyfaced boxer slit, and something far darker began to emerge. Machine Gun Jack was being born. The grief of Angelo’s death nearly tore the family apart. The store needed running and Jack’s boxing wasn’t exactly paying the bills. Keeping his gig at the docks going whilst running the store and focusing on boxing all at once just wasn’t humanly possible.

 So Jack did the only thing he could do. He laid down his gloves for good. Just when he turned pro, he remembered Capone’s wads of cash, the diamond pinky rings, the tailored suits, and he made his move. In May 1923, 4 months after his stepfather’s death, Jack approached the Circus Cafe Gang, a small but ruthless gang that operated under Capone and Toriel, hoping to run a few errands for them for some extra cash.

 Their crew operated out of a speak easy disguised as a coffee shop, the Circus Cafe at 1857 West North Avenue. This was a Capone joint and Jack knew it. The Circus Cafe gang were hardened killers, contracting their muscle out to guard booze trucks, running arms into the city, and supplying a large share of Capone and Toriel’s arsenal. Jack approached them knowing his strength would be valuable to their leader Claude Screwy Maddox.

 Unlike other outfits that lived off gambling, prostitution or smuggling, the Circus Cafe gang specialized in facilitation. They were the machinery behind the violence, providing security for major shipments, drivers for quick getaways, and men willing to settle scores. And when contracts on a rival’s head were handed down, the Circus Cafe was often the crew that carried them out.

 There was one more aspect of the Circus Cafe gang that was a little different. Screwy Maddox was an Irishman, yet he was feared and respected, mostly because he was a madman with a thirst for blood that few could compare with. His background wasn’t as important as his street cred and the services he provided. Chicago didn’t have the purest culture that New York or Brooklyn did, where ethnicities didn’t mix.

 Here, if you had the stones and the wits, your business was welcome as long as it was good business. Jack also wanted an ear on the street to find out who’d been present when his stepfather was killed. There were two main reasons really for Jack’s approach to the circus cafe. So first, he needed money and the second reason was that it got him closer to the streets and to the people operating them who knew the details of how, why, and by whom his stepfather had been killed.

 There was already a plan brewing behind that unreadable face of his before Angelo Deore’s coffin was even lowered into the ground. Jack acted as a bodyguard to Screwy Maddox. He used those well-trained fists to beat up the individuals that dared to test his boss. He roughed up people they needed to question and on a few occasions had street brawls with enemies of Toriel and Capone’s faction. Jack was fearless.

 He didn’t care what weapons an opponent had on him. He knew that his feet and his fists were quicker. By 1924, after spending 12 months with the gang, he went from bodyguard to a specialist with firearms when it came to serious violent shakeddowns and the brutality necessary to deal with rivals and double crosses, which usually ended up in the other side’s deaths.

 It was in this year that Jack began to show his knack for murder. And just like the boxing ring, the docks, and golf, he was a natural with a pistol. His natural hand eye coordination for anything he picked up played its part, and before long, he was known as the best shot in Chicago. By 1925, he’d gotten to the point where he had to recruit help to keep up with his busy schedule.

 He approached Anthony Aardo, a young gun known around the streets for his preference for violence. Tony Aardo, who went by the name Tough Tony back then, would go on to rule the Chicago outfit for nearly 50 years, learning a lot from Jack. Tough Tony became Jack’s right-hand man, and the pair of them were a rising force within the Chicago underworld.

 This was also the time spent getting all the information he needed to hunt down the killers of Deorei. Jack was stoke and quiet. He never let on that he was listening into every conversation. Being a bodyguard required a man to be silent yet within arms reach. So, he got all the information he needed by just biting his time, doing the dirty work, and not letting anyone in on the three-year grudge that he was silently planning on handling.

 In 1926, Jack finally had all the names of the Jenner gang that he needed to start going after the ones who murdered his stepfather. Over the course of eight days, he hunted down the three men that were at the scene, and one by one, he took them out. What Jack did to them and which of the gang members he did it to, nobody knows, because no one ever dared to mention it again, except for the odd whisper when the night ran late and the drink gave them courage to wonder out loud.

 And Jack himself certainly never spoke of what he’d done to each of those three men after that day. Whatever Jack had done to these men was so heinous that not even the rest of the terrible Jenner gang dared to pursue Jack for murdering their kin. He’d eventually kill a further 25 rivals for Capone, but these three were the most personal killings that he’d ever carry out.

 Word about the Vengeance killing spree spread fast. Police got Jack on carrying an unregistered firearm around this time. But Jack’s lawyer, paid for by his lucrative wage as a member of the circus gang, got him out of the charges in no time. It wasn’t just the cops that were keeping an eye on the Italian exboxer that wore an Irish name.

 Before the killings, Capone was already aware of Jack as a fellow Brooklyn native in Chicago. Capone had been eyeing him up since his boxing days. These killings and rumors that battling Jack McGurn had recently picked up a few contract killings on behalf of the circus cafe had reached the boss’s ears. At first, Capone hired Jack as a bodyguard on occasion, but the two got along so well that the arrangement became permanent quickly.

 They both loved golf, and Capone discovered during those hours on the green that there was a surprising amount of brains beneath all that muscle. Jack was observant, quiet, and very insightful. Capone learned to trust Jack’s gut and always asked his opinions after Jack listened in on meetings. Unlike the other upandcomers, Jack didn’t make a big scene about the men he’d killed or the fights he’d won.

 He watched, he listened, and his insights into people were spoton. Jack didn’t do drugs he rarely drank, and he kept up his exercise regime from his boxing days with religious regularity. Jack’s only vice was frequenting jazz bars because those quick feet from the ring were pretty impressive on the dance floor, too.

 He was reported to be an extremely good dancer. He didn’t have any serious girlfriends in the early days, but with hips that moved like that, he certainly had no shortage of interest either. Jack and Capone even dressed alike. Capone was more partial to a little flare from time to time with his suits, whilst Jack preferred the classy three-piece tailored fit that never goes out of style.

 Together, they were the picture of old Hollywood gangster glam. Around this time, Jack moved into the 10story Lexington Hotel at 2135 South Michigan Avenue, the headquarters of Al Capone. Jack loved the gym so much that Capone had a gym built specially in the Lexington Hotel. So that Jack, who was the best of his hitmen and bodyguards, could train the others how to be as physically fit as he was.

 As Capone believed that’s what made Jack better than the rest. Although Capone had four bodyguards at any one time, Jack was his constant shadow. He’d be present at meetings, by his side at family occasions, and as we can see from this picture, even behind him, keeping a watchful eye when Capone took his son to baseball games.

 And there was good reason for Capone to take his security so seriously because during the time that Jack had been with the Circus Cafe Gang Chicago because of the lucrative profits that prohibition had brought had become an absolute bloodbath. It was called the Chicago Beer Wars, but the word war was an understatement.

 In 1924 alone, over 130 gangland killings took place in Chicago. And the most prominent of those was Deio Banyan, the cheeryfaced Northsiders leader, who, like Jack’s stepfather, had been killed by the terrible Jenners. By 1925, the terrifying Haimey Weiss, who assumed leadership of the Northsiders after the death of his boss, Deanie, had already killed bloody Angelo Jenner, his older brother Tony the Gentleman Jenner, and was partly responsible for the death of Mike the Devil Jenner, who was killed by police after a public shootout with

Weiss. After half of the Sicilian brothers were dead, the Jenners had lost their main enforcers and had retreated. And now little Italy belonged to the Northsiders. But they weren’t done there. In the same year, Johnny Torio was ambushed by Haimey Weiss and his second in command, Bugs Moran, outside his home.

 He narrowly survived the attack, but the 43-year-old Toriel decided he’d had enough and handed over the outfit to Capone, retiring back to New York after declaring Chicago too hot to handle. Now, in the summer of 1926, the Chicago Beer Wars was still tearing up the streets, and the clashes between Capone’s outfit and the Northsiders resulted in weekly drivebys, murders, car bombings, contract killings, and booze hijackings.

 It was an incredibly violent time, so Capone had a good need for men like Jack around him. to Jack. Well, he took his role very, very seriously, proving himself effective, killing rivals before they even got close to Capone and stopping reporters getting close to the now famous Scarface, as the press now referred to Jack’s boss as.

 But it was in the height of the Chicago Beer Wars for the rest of the roaring 20s where Jack really showed his worth. During the 2-week New Year celebrations the crew held at the Lexington Hotel, Capone and Jack came up with a strategy to unleash hell on every rival that Capone had circling his territories and gain Capone control of something else he also desperately wanted.

 The Union Siciliana, a Sicilian American organization which predated the mafia in Chicago. Capone wasn’t Sicilian, so he could never be president. But he figured if he whacked every leader, he would eventually be the head of it. They were going to turn up the beer wars to 11. And this time, Capone had a plan and a man to exact that plan for him.

 Capone gave Jack the green light to put together a crew. And this crew, with Tony Aardo as his right-hand man, became the deadliest group of killers in America. To name a few, there was John Scaliz and Albert and Selme, whom people called the killer twins. They weren’t related at all, but they almost always operated alongside each other.

 They’d worked as hitmen for the Jenner gang before, but when they heard that Jack had killed three of them, and that Al Capone himself had a price on the rest of the gang’s heads, they were smart enough to defect to Capone’s outfit before their skin was featured on tomorrow’s front pages. The killer twins were the two men who’d pulled the trigger on Dei Oanyan.

 The very murder that kickstarted this entire war. Scalis and Anelme were as feared as Jack was. To them, a job was a job. Be that man or whiskey, it didn’t matter. As long as they were paid well, they wouldn’t care less what was asked of them. Another assassin in this crew was Sam Golf Bag Hunt.

 nicknamed so because he carried his trusty gun and rifle around in a golf bag to minimize suspicion and he was absolutely deadly with both of those weapons. Next came Frankie Rio, who was an interesting figure to say the least. It’s hard to say who was closest to Capone, whether it was him or Jack. His fierce loyalty to Capone was second to none, and he often acted as Capone’s personal bodyguard, too.

 Frankie Rio, like Jack, had a whole lot of brains behind that icy stare of his. Jack and his band of killers started by targeting the remainder of the Jenna gang’s associates. Not only was Capone at war with the Northsiders, but he was also locked in a bloody war with what was left of the Jenner gang as well. This was because Angelo Jenner, before he was murdered, had been the president of the Union Siciliana, and Capone desperately wanted that title for himself.

 First up was the Jenner’s principal enforcer, Oatzio Tropea. Tropea had killed a few of Capone’s men in this war, and Jack gave the honor of this killing over to Scaliz and Anelme. Because as former members of his crew, Jack wanted them to prove their loyalty to Capone. On February the 15th, 1926, the twins drove past him on the southwest corner of Taylor and Halstead Street.

 Tropeo was hit with a shotgun blast from an open window and died instantly. A week later, his right-hand man, Veto Basonei, and his personal driver were found in separate ditches in Oak Lawn. Both bodies were found miles apart from each other, and they both had the weapon that killed them placed next to them. This was Jack’s signature calling card when he wanted people to know that it was him that did the deed.

He left the gun on top or near the bodies. And for this reason, Jack went through firearms like Capone went through cigars. On April the 27th, 1926, two leaders of the Westside O’Donnell gang, a smaller Irish faction that Capone had beef with, James Doaty and Thomas Red Duffy, of whom no photograph survived, were gunned down.

 Assistant States Attorney Bill Mcswigan was talking to Duffy and Doaty outside the Pony in Saloon at 5613 West 12th Street in Cicero, Illinois. A dark car with curtained windows pulled up next to them and the snout of a Thompson submachine gun poked through the gap in the curtains, showering all three men with a hail stom of bullets.

 Duffy and Doaty died at the scene as well as a civilian that happened to be passing by. Mcwigan, just 26 years old and the son of a prominent sheriff, died a few days later in hospital. At first, police tried to make it look like Mcwigan was meeting the gangsters because he was so passionate about bringing down the horrendous amount of crime in Chicago.

 A hero that was willing to walk the streets himself and fight organized crime. He definitely put enough of the Italian gangsters behind bars to justify a price on his head. However, he made no secret about how he was going to bring an end to bootlegging, directly threatening Capone’s empire. But there really isn’t any good reason that a man that was supposedly so against organized crime should have been talking to the leaders of a violent Irish gang outside a club unless he was in their pockets himself. The truth was that Mcwigan was

only targeting Capone and had a habit of getting the Irish gangster charges dropped or significantly reduced and Capone and Jack were not having it anymore. Years later, ballistic experts tied slugs from the scene to a Tommy gun which was known to be Jacks. Jack was targeted at least twice by Northside gangs by the time that July rolled around.

 After the Mcwigan hit, he’d killed at least three Northsiders, and they couldn’t allow him to continue for much longer, or there wouldn’t be any of them left by the end of the year. Luckily, they were terrible shots that almost solely relied on driveby shootings that hit every single civilian in the vicinity, but no bullet ever managed to find Jack.

 Jack also developed an ingenious strategy to take out targets. He’d rent multiple hotel and hostile rooms surrounding a location that he knew rivals frequented often. He’d then equip himself and all of his other men with machine guns. Once they’ taken out the person that they’d come for, the other hitmen would take out any bodyguards or associates that tried to run.

 When the job was done, they’d leave their weapons at the scene and get to the street where they’d blend in with the crowd that formed until they could make it to multiple getaway vehicles stationed at pre-planned locations. Capone had his fair share of attempts against his life, too. The most significant of which occurred on September the 20th, 1926 at the Hawthorne Hotel in Cicero, Illinois, where Al Capone kept a headquarters.

Northside gang leader Haimey Weiss led a 10car motorcade to the Hawthorne to prepare for what would have been the most epic execution in mob history, if only they’d managed to pull it off. The plan for the ambush was grand, dramatic, and totally outrageous. In a choreographed scene that would have put the biggest Hollywood directors to shame, all at the same time, the Northsiders opened fire from every angle, peppering the Hawthorn and hoping to hit Capone through the window where they knew he would be holding court with

the rest of the outfit. The bullets tore through the walls and windows and absolutely decimated the hotel. The northsiders didn’t stick around to see however that Capone emerged from the room unscathed. When the firing squad started unloading their magazines, Frank Rio threw his body over Capone, forcing his boss down to the ground and saving his life.

 Neither Rio nor Capone had any wounds to show for their miraculous escape. A passerby was grazed on the leg and a woman lost an eye to shrapnel and another man was hit in the knee, but none of them had life-threatening injuries and Capone tracked them all down anyway and paid for all of their medical expenses. Police stopped counting the shell casings after they reached a thousand rounds.

 Even decades later, mafia enthusiasts still go to the original location with metal detectors, hoping to find a century old bullet as a souvenir. This outrageous attempt started an everinccreasing violent tit fortat between the Northside gang and Capone’s outfit. 3 weeks later on October the 11th, Capone ordered Jack to take out Haimey Weiss for good, who quite literally terrified Capone and was known as the only man that Al Capone ever feared.

 So Capone had good reason to want him dead. Jack had been using his tactics of casing Haime’s routine with Golf Bag Hunt, and together they rented two apartments next door to the Northsiders headquarters, Scoffield’s Flower Shop at 738 North State Street, which offered them a view directly across the road of Scoffields of the Holy Name Cathedral, where the deeply Catholic Northsiders attended mass each day and a place where Weiss was always known to park his car At 400 p.m.

 on October the 11th, 1926, Weiss and another Northsider called Paddyy Murray predictably emerged from their parked car next to the cathedral. As they crossed the street to Scoffields, golf bag hunt opened up with a shotgun and Jack with a Tommy gun. Weiss is struck 10 times and dies in the ambulance on the way to the hospital, whilst Patty Murray is struck seven times and dies where he falls.

 The stampede of terrified civilians caused the necessary amount of chaos needed for Jack to blend into the crowd. He left a Tommy gun on top of a dog kennel a block away before getting into a car to speed off into the afternoon. Now that Haimey was out of the picture, Bugsaran assumed control of the Northsiders and the Guzenberg brothers, Frank and Peter, took up arms with him to continue this little murder merrygoround.

 They were longtime enforcers and hitmen of the North Side gang, and they took the hit against their leader, Weiss, as a personal insult and vowed revenge. In November alone, there were six driveby shootings carried out by the Northsiders against Jack, but remarkably, every bullet missed. Drivebys were terribly ineffective at killing the actual targets, but fantastic at hitting women and children walking past in the background.

 For all of the murders that took place in 1926 in Chicago, there were almost as many civilian casualties as they were gangster deaths. Most of the civilian deaths were thanks to north side bullets, thanks to their insistence on sticking to driveby shootings. That was the difference between Capone and the North Side forces.

 The north side relied heavily on their numbers, drowning their enemies, while Capone’s hitmen were thoughtful, targeted in their approach, and unafraid to step into the battlefield themselves. Besides, they couldn’t risk hitting the public. Not that they didn’t on occasion, but they kept their feuds between them and the foes, going out of their way to avoid civilian casualties because Capone was incredibly interested in maintaining a favorable public image.

The tit for tatac killings continued for the rest of 1926. This year culminated in hundreds of suspected deaths and is considered the most violent gang related city death count in this bloody era of prohibition. There were 76 confirmed gang related murders that came through the morgs in Chicago alone.

 And that’s not counting the dozens of civilians that got killed in the crossfire or the mobsters that had simply disappeared off the face of the earth and who’d never be seen again. 1927 kicked off with Jack deeply invested in bringing up the quality of Capone’s security detail. With Haimey Weiss now out of the way, Capone ordered Jack to take care of any northsiders that were still around.

 Capone promoted Jack to general status, giving him full authority over everyone in Capone’s inner circle. He placed Tony Aardo as the boss’s personal bodyguard on the rare occasion that Jack wasn’t shadowing him. However, it’s in the intelligence sphere that Jack really shined. He employed taxi drivers, cafe owners, and kids around Chicago to gather information.

 Members of the general public were even more valuable. Capone was already a hero thanks to his generous charitable contributions to the public. Capone looked after the everyday man. He was a real life Robin Hood. And when they notice strangers loitering around Capone’s offices or places he was known to frequent, Jack got word of it in minutes.

 This information from the spies allowed Aardo to foil dozens of sniper and driveby attempts on Capone’s life. They sent searches ahead of Capone’s arrival to sweep the surrounding hostiles and buildings, chopped and changed routes, and put their own snipers on rooftops. The level of espionage and heightened security around Capone at this time was so effective that government officials later adopted their methods, too.

Everyone marvels at Capone’s operation and how effective his detail was at protecting him. and oftentimes civilians, too. But they largely forget that it was Jack’s smarts and out ofthe-box thinking that made it all possible. He was a bonafide genius on the front lines and the main reason that Capone’s outfit were winning the beer wars.

 By the summer, things were heating up for the takeover of the Union Siciliana. Everyone wanted in. But to do that, they needed to take out Capone, who had more men on the inside and more public favor to keep him there. Capone’s personal conciglier and right-hand man, Antonio Lombardo, was elected as leader of the Union.

 So, in other words, Capone now had the power. The main rival for Lombardo and Capone was Joey Ielo, a Sicilian bootleger who had taken control of what was left of the Jenner brothers’s gang. He immediately sought an alliance with Bugs Moran, whose north side crew had wiped out the Jenners. Immediately, Illoo and Moran agreed that they were tired of the Guzenberg’s brothers continued failed attempts to take out their main rival and his deadly efficient second in command.

 They put out a nationwide bounty on Capone. $50,000 to the man that brought them the Italian Robin Hood’s head, which was just short of a million dollars in today’s money. Jack killed seven wannabe assassins himself. He placed a buffalo nickel in each of their palms as a souvenir for their troubles and as a message to anyone else who might be thinking of taking a shot at his boss and claiming the bounty.

 As was the case on September the 5th, 1928, when two small-time gangsters, Edward Wescott and Frank Cley, were executed with three bullets each to the back of the head and dumped in Reese Park on West Fullerton Avenue in Chicago. The murder weapon was found on their body and a Buffalo nickel in each of their palms, Jack’s signature calling card.

 Iello himself even tried to sneak poison into Capone soup at his favorite restaurant, the Bella Napoli on South Holstead Street, owned by Capone ally Diamond Joe Espazito. Luckily, the chef snitched and his life as well as Capone’s was spared. Whilst half the country were running around trying to kill Capone, keeping Jack and Aardo too busy to protect the other figureheads, they took out Tony Lombardo, head of the Uni and Capone’s right hand.

 On September the 7th, Frank Guzenberg and Bugs Moran working on information passed by Ielo approached Lombardo and his two bodyguards outside a restaurant called Racklios on the corner of Madison Street and shot Lombardo at close range. Tony Lombardo and his bodyguard died instantly. Capone was furious. He suspected Ielo was behind the hit, but under Jack’s advice, bided his time before launching a fullcale assault.

Another Capone ally, Paty Lordo, was appointed the head of the Union, meaning that Capone’s grip on power didn’t slip. The price on Capone’s head was causing Jack to run around in circles. They killed another potential hitman hiding on a rooftop or inside a motel room almost every week for the next month when the security sweeps found them.

Around Christmas, Jack got arrested for suspicion of murder. But the charge didn’t stick. So, police, now fully aware of just how dangerous he was, decided to hound Jack’s every move, arresting him from everything from several weapons charges to vagrancy. They knew full well that no matter where they found Jack, he’d be carrying a pistol on him at least, or he’d be loitering outside a building as part of a wider security or surveillance operation.

 Not that Jack made it easy for them, as at this time he used more aliases than any mobster around at the time, switching between his stepfather’s surname, Deorei, and his mother’s maiden name. Or he’d simply just make a new one up for that month and discard it after a few weeks for another. But as 1927 gave way to 1928, the Northsiders finally got their man.

 On March the 7th, the Guzzenberg brothers closed in on Jack as he moved to take over a beer racket deep within Northside Territory. He attended a takeover celebration at the McCormick Hotel on the corner of Ontario and Rush Street when the brothers struck. Jack was hit in the right lung and shoulder before his guards rushed forward to shield him.

 The brothers managed to get away whilst Jack was rushed to the Alexian Brothers Hospital. Everyone in Chicago figured that it was the end for McGurn, but despite being shot in the chest, he survived after surgery in a hospital. McGern recognized the Guzenbergs as the shooters. “Char police asked him who did it.” “Of course I know who shot me,” he declared from his hospital bed without revealing names.

“When I’m well again, I’ll settle this thing myself.” The papers dubbed him machine gun Jack McGurn and the nation swooned over the killer romanticized simply because he was remarkably good-looking. Ultimately, the nickname stuck and his legend grew. Machine gun Jack spent those recovering days seething with rage that anyone could have gotten so close to actually killing him.

 It’s here that he lay with only nurses for company and two armed guards outside his door that he started planning the ultimate revenge. He’d avenge his attempted assassination, clear the way for Capone to take over, and he’d end this neverending war all in one clean sweep. Jack’s military mind was formulating, mulling over the details of the perfect hit he was going to orchestrate to reclaim his throne and to finally rid them of all their north side problems.

 Jack bounced back remarkably fast. He was incredibly fit and at just 25 years old, he was young and healthy and therefore in a much better position to survive such a deadly assault than other men his age. To the doctor’s shock, in just two weeks, he was back on his feet walking around. Jack increased his security.

 Not that it helped much because a month later, he was attacked again. Just as he was walking out the courtroom for the latest charge that one of Capone’s many lawyers managed to get him off of, James Clark and Billy Davin, a couple of Bugs Moran’s enforcers, open fire with machine guns. Jack’s face, still bearing the marks of the previous attempt on his life, was peppered with concrete when the bullets hit the nearest building and another bullet grazed his shoulder.

 A week after this latest attempt, the Guzzenbergs tried again. They drove up beside his car on a Chicago street and one of them unloaded a Tommy gun. As the slugs whizzed by, McGurn leapt from the car for refuge next to a building. The brothers fired more bursts from the Tommy gun, but their shots missed.

 And McGurn, remarkably unscathed, knew once again who had tried to take his life. There was a lull in activity between the spring and fall of 1928. There was still plenty of street ambushes, hotel hits, and drivebys that wounded and occasionally killed lower and mid-level members and associates on both sides. But both factions were taking a step back from major hits and taking over territory.

 The year’s long back and forth had exhausted them all. A season to restructure and to think up new strategies was in order. In November, Jack shattered that lull and not by a mob related attack. Surprisingly enough, the popular jazz singer and comedian Joe E. Lewis had a contract to sing at the Green Mill at 4802 North Broadway. a speak easy which was owned by Capone and Jack.

 Lewis suddenly ended his very lucrative contract with the Green Mill in favor of the new rendevu cabaret located at 622 West. This was a Bugs Moranowned club and they got Lewis to agree by offering him partial ownership in the rendevu. If this wasn’t bad enough already, Lewis had the goal to ridicule Jack during his opening performance, much to the crowd’s amusement.

 The place was packed to the brim, so news about the jabs reached Jack in no time. Capone was salty about losing business, but Jack was enraged that Lewis had dared to make a public spectacle of him. So Jack retaliated by paying Lewis a visit on the 10th floor of the Commonwealth Hotel on 2757 North Pine Grove where Lewis’s room was.

 A maid working the hall that night saw three men knock on the door and a few minutes later heard screaming coming from inside the room. Jack stabbed and slashed Lewis a dozen times. His skull was left fractured, his throat was slashed, and a chunk of his tongue was sliced off when the blade went through his left cheek.

 Jack and the two men left the room, thinking that Lewis was dead, but he managed to survive the horrendous assault. Lewis would spend months relearning how to talk and swallow, but never mentioned Jack’s name, as he knew he’d end up dead if he did. He eventually returned to performing, but never managed to get that husky tone that sold so many records back to its former glory.

 Jack, who’d always preferred to remain in the shadows, was becoming something of a paper seller. After the media formed over the previous assassination attempt that left him fighting for his life, they turned him into a B-rated celebrity, a machine gun jack made for press gold. and the press and their readers couldn’t get enough of him.

 He wasounded as much by the reporters as he was by the police. The only upside to this newfound fame was the vaudeville villain jazz performers that fell over themselves to share his bed. One of those starlets was 22year-old dancer and actor Louise Rolf. She was a former model, former chorus girl, an upandcoming actress, and multi- divorcee.

 Louise went through men at an astounding rate. But Jack, well, Jack was different. He was the one man that Louise never tired of. No matter how many times she moved on, somehow they’d always end up back together. Jack had never been devoted to anyone before. But for Louise, he took time off between hits and arrests to take her on vacations, and they were photographed together at premieres and Hollywood parties.

 Jack only left Chicago for two reasons. An out of town assassination or to take his blonde beauty on holiday. Jack’s numerous paper appearances and now his highprofile relationship with a starlet made him so recognizable that Northside gangsters opened fire on him if they saw him in the street, even if they were in a neutral zone.

 This was a huge problem for the wider Capone faction because Capone was the media man. That was his job. The hitmen, the bodyguards, the enforcers, and all the rest relied on their anonymity to conduct business. Now, they were being named and their faces were being recognized purely by being associated with Jack.

 No matter what he’d done for the outfit or how many men he’d killed for them, Jack was only as useful as long as he remained invisible. Understandably, tensions started to brew within the Capone ranks. So, Jack devised a plan that would quite literally shock the nation, become the crime of the century, and most importantly, get him back on good terms with his boss.

 Towards the end of 1928, Bugs Moran was having a supplier problem and the Northsiders didn’t have enough booze to meet the demand of their clubs and their speak easys. So, Moran targeted Capone’s beer trucks. Capone had the finest whiskey smuggled into Chicago from Ontario, an operation that depended heavily on his alliance with Detroit’s notoriously violent Purple Gang.

 The purples smuggled the whiskey across the Detroit River and delivered it to the many warehouses in Chicago that Capone kept. Moran knew the back roads that the purples would take and began to hijack his trucks. The northsiders shot the drivers and the security dead and stole the whiskey. Capone was losing men, trucks, booze, and money at an alarming rate.

 So naturally, the outfit were going to retaliate. But continuing this cartoonish daily exchange of bullets wasn’t going to magically solve Capone’s overall north side problem. They needed to reconfigure and tackle this from a different angle. Capone was always anxious about his public image and knew that taking out Bugs Moran, who was also by now a media darling, would turn the public against him.

 But even he couldn’t sit back and let Bugs and the Northsiders get away with what they did next. On January the 8th, 1929, Peter Guzenberg and James Clark visited Paty Lordo’s thirdf flooror apartment on West North Avenue for a meeting with the new head of the Uni, a meeting that was arranged by Joey Ielo. For nearly an hour, Lordo and his guests drank and laughed until gunfire shattered the calm.

 His wife rushed in to find him slumped on the floor, a wine glass still in his hand, and he was shot 11 times. The killers walked out, one even pausing to place a pillow beneath Lordo’s head before leaving the scene. For Capone, the murder of Lordo was intolerable. But for Jack McGurn, it was an opportunity. He formally requested permission to eliminate Moran and his crew once and for all.

 Not over bootlegging disputes, but to protect his own standing. Jack knew that his title of general would not last unless he silenced those hunting his blood and regained the crew’s trust after his face had filled the front pages for most of 1928. The time for games was over and this war needed to end. Capone agreed and so did the rest of the outfit and the pieces were put in place months in advance.

 The outfit arranged for Capone to be at his Miami Beach mansion and tipped off reporters on his whereabouts to make sure that there was plenty of evidence to prove that Capone was out of town throughout late January and most of February of 1929. Louise, Jack’s pretty little partner, allowed the press to follow her to the Stevens Hotel, now the Hilton Chicago, at 720 South Michigan Avenue, where she told them that her and Jack were having a romantic weekend together for Valentine’s Day, as any doting couple with money would. Louise’s part to play

in all of this was pivotal. She’d be digging deep into her acting skills soon enough for her role in this whole shebang. The other big players in Capone’s faction that police were following almost permanently now like Capone’s brother Ralph and Frank Niti who was another young enforcer out of the outfit also sought out the spotlight.

 It’s probably a good thing that at this point Niti wasn’t a part of the main set of affairs because he and Jack didn’t like each other at all. Niti was an upand cominging hitman and quite good at what he did. He felt that Jack was too full of himself, too in the spotlight, and he didn’t like taking orders from him. Call it office politics.

 But Niti felt that he deserved the job of general, and that Jack was standing in his way of getting there. Nevertheless, figures like Niti and Ralph were placed at public establishments like restaurants where they’d be seen by as many people as possible, and they made sure that their appearances would be as far away from Jack’s target as they could be.

 This last move was ingenious. Not only were all the most watched figures all covered by an alibi, they were the ones attracting police attention. with them spread out over the city. They’d be taking a few officers with them to the farthest points of Chicago. Why were they going to all this effort then? That was because Jack knew that Moran and his top men would be at the SMC Cartage Company, a Northside warehouse at 2122 North Clark Street in the Lincoln Park neighborhood at 10:30 on the morning of Thursday, February the 14th. On Jack’s

orders, the head of Detroit’s Purple Gang, Abe Bernstein, approached Moran while posing as an independent hijacker, offering a shipment of old log cabin whiskey at a price which was too good to ignore. For Moran, who was still scraping by through his dangerous work of hijacking the outfit’s trucks, a violencefree deal was easy to accept.

The delivery was set for 11:00 a.m. on Valentine’s Day, and Moran instructed his top men to gather at the garage for a closed door meeting. They would need to be present to help with unloading and between the accountants, the enforcers, and the fronts draw up a plan to move the liquor safely into circulation without the outfit knowing.

 There were eight people scheduled to meet there that morning. Moran, the leader, Albert Cashell, who went by the alias of James Clark, Moran’s second in command, and one of the men who ambushed Jack when he left the courthouse a year ago. Willie Marx and Ted Newbury, who controlled prominent uptown nightclubs for the Northsiders, Adam Haer, the Northides bookkeeper and an unproatic man.

Overall, he was extremely valuable to Moran for his skills, but ha was not interested in wheels and deals. He had seven children to support and made a point of staying out of trouble, a position that Moran respected. Albert Wine Shank was also due that morning. He ran several dry cleaning fronts for Moran to funnel his dirty money through.

And last up with the Guzzenberg brothers, Moran’s main enforcers. Also in the garage was the gang’s mechanic, John May. May almost certainly had no involvement in this meeting and was just working on the gang’s cars, but was accompanied by his dog, a loyal German Shepherd named Hibball, who was ever present with John May.

 Also present was a former optician who gambled so much that he’d made it his career, Reinhardt Vimemer, a man who got a thrill from associating with men like Moran, but wasn’t strictly involved in any of their dealings. May and his loyal canine Hibball arrived at 8:30 a.m. to unlock the doors. There was a light snow falling that morning, dusting sidewalks and streets like confection as sugar.

 At approximately 9:30 a.m., the Guzzenbergs arrived, dusting the sparkling flakes off their jackets as they walked in. James Clark and Adam Haer entered next. By then, the Guzzenbergs had coffee going, and almost everyone stopped to scratch highball behind the ears. Even Harden killers couldn’t resist a good boy.

 Wine shank, the frontman, and Reinhardt Vimemer, the optician, arrived last. That means there were three of the men who’d not yet arrived. Willie Marks and Ted Newbury were running late, as was Bugs Moran. Stationed across the street were three Purple gang members, brothers Philillip and Harry Keywell, and Eddie Fletcher.

 They rented rooms at 2125 and 2130 North Clark Street, right across the street from the SMC Cartage Company and a place where they had a direct line of sight to the garages door. Even with a clear view, they still managed to mistake Wine Shank for Moran and signaled the gunmen prematurely. An easy mistake to make because all of the men were dressed in suits, long coats, and hats that obscured their faces somewhat.

 They dialed up Screwy Maddox, who was waiting with McGurn and his team of killers at the Circus Cafe just a few blocks down the road. The four gunmen arrived at approximately 10:30 a.m. The Cadillac they drove was painted to resemble a police car. Two of the men were dressed in police uniforms, while the other two wore long winter coats and fedoras.

 From a distance, this did truly appear to be a typical frisk by some board policemen. Though Tommy guns and sworded off shotguns were not usually standard police weapons just as the Cadillac pulled up outside the garage, Moran, Willie Marks, and Ted Newbury were walking up the street seconds away from entering it themselves. They casually turned on their heel and walked the other way, assuming that this was another police shakedown for the sole purpose of intimidating the mobsters.

 It happened all the time and it was usually over within a few minutes when the authorities inevitably found nothing. But still, it was an inconvenience that they’d rather avoid. They entered a nearby coffee shop, positioning themselves by the large storefront windows to keep the garage in sight. They’d go back once the cops had left the scene.

 Inside the garage, the four assassins entered and ordered everyone to line up facing the wall. The group complied. Used to this kind of thing by now. They weren’t even afraid of the guns in the policeman’s hands. All that was going to happen was that their pockets would be searched. The cars in the shop would be given a look over and then they’d leave while the coffee was still hot.

 Highball tied to one of the cars strained against the chain to join his master by the wall. When all the men were lined up with their hands behind their backs, all hell broke loose. Heat. Heat. [Music] The gunmen aimed high. All of the 50 round drum magazines from the Tommy guns hit the seven men from the waist up, tearing through their vital organs.

Every man standing in line was dead before they hit the ground. All except for one. The sudden surge of popping sounds coming from the garage confused bystanders. It was so sudden and over so quickly that no one quite knew what to make of the ruckus or the police car speeding away like a bat out of hell. A woman living in an apartment next door went inside to see what had happened, only to find an absolute bloodbath.

Frank Guzenberg lay on top of the other bodies, his breaths gurgling as he drowned in his own blood. He’d been shot 14 times. When police arrived, every lookout had disappeared. Moran, Marks, and Newbury were standing amongst the gathering crowd when the squad cars and ambulances arrived just minutes later.

From a young boy running through the crowd, Moran found out that there’d just been a gunfight between a couple of gangsters and the cops, but that everyone was dead. Almost as if there needed to be confirmation for the boy’s breathless tale, the coroners started carrying out the bodies one by one. As Moran stood there in horror, he counted the stretches.

 There were six corpses covered in sheets that were already soaked through with blood and another that was rushed away to the hospital. That made seven deaths, six of them being the most important figures in Moran’s operation. This was no shootout. This was on Capone’s orders and by Jack’s planning. That was something that Moran was sure of.

 Only Capone kills like that, he told the press a few hours later. Hibball was found cowering and howling under a car. The blood pulled so wide that his paws were saturated with the gore. One of the first reporters at the scene offered to adopt him, but Highball was so traumatized by the event that it was kinder to euthanize him just a few months after the ordeal.

 Frank Guzenberg managed to cling to life for a few hours. Police even tried to question him while doctors scrambled to save his life. In his final moments, he managed to croak, “Nobody shot me.” and then he died. Frank abided by the code of silence until the very end. Through questioning, they discovered three rooms rented around the garage weeks in advance.

 Another man observed a taxi dropping off spies and lookouts every day between 9:00 in the morning and picking them up at 3 in the afternoon. Police found the Cadillac. It was disassembled and burnt up. The coats, hats, uniforms, a police siren, and one of the Tommy guns as well as a Luga revolver were found at the scene, too. Other than the fact that this whole operation stank of Jack’s outstanding military planning, police had nothing.

They found the pair at the Stevens Hotel on the 27th, but Louise swore high and low that Jack was with her in the hotel room all day. She never cracked under the hours of interrogation, but she did go into an embarrassing amount of detail about what they did inside that room that left the officers blushing.

Apparently, those acting jobs she landed weren’t just because of her looks. She spoke openly to the press at every chance she got, making sure that everyone knew that she and Jack were together that day. They dubbed her the blonde alibi, a title she wore like a badge of honor. Witnesses identified a few members of the Purple Gang and the Egan Rats gang as lookouts.

 Not surprising since the Purple Gang especially had enough reason to hate the Northsiders for all those hijackings they put out on their boost trucks all these years. The three other gunmen accompanying Jack were likely to be the killer twins, John Scaliz and Albert Anelme, and an out oftowner, Fred Burke, an Egan Rats gang member who wouldn’t have been recognized by any of the gang members.

 So, it’s likely that he was one of the fake policemen who ordered them to line up against the wall. But that’s all they had. Vague descriptions and whispers. But the Saint Valentine’s Day Massacre, as it had come to be known, had been an incredible success for the outfit. And truth be told, Bugs Moran was finished.

 He’d lost his bookkeeper, his main enforcers, his second in command, and a massive amount of his business fronts after the outfit swooped in. After the massacre, not only was there no one left who had the skills to pick up from those who’d been killed, the few that did remain were now too scared of Capone to step into the line of fire for a man who’d lost control of his empire.

 Joey Iel, now Capone’s main rival, fled to New York, knowing that he’d be the next one lined up against the wall if he dared to stay in town. With every charge against Jack dropped, thanks largely to his blonde alibi, Capone’s outfit took care of any of the last North Side stragglers, Jack stayed out of the heat of things for the rest of the year, sticking to planning in the background until the heat died down.

 Not that it did. The St. Valentine’s Day massacre had enraged the public. The amount of press that this received was incredible. Every guilty party or suspected individuals wereounded by reporters. The exposes and the coverages lasted for months unlike any previous hit had before. Seven men killed in broad daylight with this level of violence was too much for the whole of America to handle and it quite literally shocked the nation. The St.

 Valentine’s Day massacre was the catalyst that forced lawmakers to start changing laws to bring the raging gang problem in the United States under control. One of the main investigators who had Jack in his sights was Julius Rosenheim, and he was killed on February the 1st of 1930 on Bolan Street, just a block away from his home.

 It’s unclear who Rosenheim was talking to or what information he got his hands on, but the word on the street was that he had Jack banged to right. Whatever he found out, it was important enough for Jack to finally come out of the shadows to do the job himself. Jack and Tony Aardo were found a few blocks away.

 They discarded the weapons used to kill Rosenheim, but they still carried their personal weapons on them, so they were detained for those. As Jack walked out the courthouse for those weapons charges, the press fell on their favorite handsome bad boy. When asked if he knew that Rosenheim was dead, Jack was quoted as saying one of his most famous lines, “Dead, I didn’t even know he was sick.

” But this time, Capone stepped in himself and told Jack to lay low. The heat from the massacre wasn’t showing signs of slowing down. And Capone’s entire outfit, all of his businesses and every associate connected to him were under an extreme amount of pressure from authorities. No one in the outfit wanted to be associated with Jack anymore.

Being with him meant that police automatically put a target on your back. It’s not that they aggressively pushed him out of the outfit. It was more that when he walked into a room, everyone took that as their cue to leave. The message was clear. Jack had done great things for the Chicago outfit, but with greatness comes a price.

 It was time for him to step away. The government’s first big move on the back of the St. Valentine’s Day Massacre came in April of 1930 when the Chicago Crime Commission compiled its public enemies list, publishing their top 28 most corrupt Chicago gangsters and criminals nationwide. Jack was fourth on that list. Capone ranked first.

 Moran, Aardo, and Iel were on there, too. With police now investigating them all, Jack took Capone’s commands seriously. He stepped away, moved into a house at 224 North Kennelworth Avenue in Oak Park, Illinois, and married his blonde starlet, Louise Rolf. For all of 1930, Jack took to golfing and going on beach getaways with his new wife.

 The effects of Jack’s departure was felt immediately. When Jack was in charge, things were bloody but organized. Under his command, drivebys and street gun battles were at an all-time low. More gangsters were dying, sure, but civilian lives were spared as a result of his military level planning. The moment Jack stepped away, all hell was unleashed in Chicago streets.

 Overnight, the showdowns became unorganized, erratic, and completely out of control. Not that Jack paid much attention to the chaos. By then, he was a silent partner at the Evergreen Golf Course. the same grounds where he had once caddied as a teenager. The place had become a hangout for mobsters who played cards, golfed, and talked business in the open air.

 Jack even returned to teaching youngsters the game, and on more than one occasion, he shared the course with Bing Crosby as his golfing partner. Jack had every reason and all of the means to retire the life of a hitman and warfare general with full honors. He had enough money coming in from his stakes in the golf course.

 His lovely wife was everything he wanted and his mother plus almost all of his siblings were looked after. He’d done a reasonably good job of keeping them off the streets. Only two of his brothers were ever linked to any kind of crime. Still, their dealings were minor in comparison to the 25 known murders that police suspected their big brother of.

 But Jack wasn’t known as Machine Gun Jack for nothing. And when his old boss called on him, he put down the nine iron and picked up his old friend, the Thompson submachine gun. In late 1930, Capone asked Jack for one last favor. Joey Iel was back in town, and he needed this final hurdle to be taken care of once and for all. Jack obliged, setting up lookouts at all of Iello’s known accompllices apartments and businesses.

 In a few weeks, he found Ielo’s wife and kids and began tracking them instead. It’s through their scheduled visits with Iello that he was able to pinpoint his hideout to 205 North Kmar Avenue, a stone throw from Reese Park where Jack had already spilled blood. In typical Jack fashion, several gunmen and multiple getaway cars were stationed around the building.

 When I opened the front door on his way to a barber’s appointment on the morning of October the 23rd, 1930, he was peppered with 13 rounds from a second floor window of an apartment building across the street. Somehow, Illo managed to stumble around the corner. Instead of getting out of the line of fire, I walked right into another submachine gun positioned on the third floor of another apartment building.

 The shooter emptied all of his bullets into Iello, continuing to hold the trigger long after he fell to the ground. That gunman was one who was living up to his nickname, Machine Gun Jack McGurn. The gunman fled, torching their getaway car and guns on the way. Iello was pronounced dead at Garfield Park Hospital.

 He’d been shot an astounding amount of times. 59 bullets were removed from his body and in total they weighed over a pound. Jack and Tony Aardo were arrested just a few blocks away with their personal firearms still on them. Predictably they were arrested on carrying unlicensed weapons that didn’t match those at the crime scene and they got out of those charges without any evidence to support them having any part in Iel’s murder.

 After the IEL hit, Jack did retire and for a few years was doing well for himself. He even tried his hand at professional golfing. Like his boxing career, he was a natural. He was never any Tiger Woods, but he was good enough to fill up a competition lineup. He played under the name Vincent Jabardi, another variant of his birth name, and Louise was always on the sidelines cheering him on.

 Capone got taken in for tax evasion in 1932, sending him to Alcatraz for seven years. Things quietened down in Chicago with all of the big hitters off the streets for the time being. Though Jack’s caddy said despite this that Jack always had his trusty Tommy gun hidden in a golf bag whilst he was on the course, just in case.

 However, his name change that he was using at the competitions, which sounded very similar to his birth name and his face in the paper from these golf tournaments got the attention of the police. He was still under suspicion for multiple murders and they never stopped looking for him. Once they tried to arrest him in the middle of a tournament, they allowed him to finish his game, standing at the back looking menacing, thus destroying the run he had going and throwing his chances of placing in the professional league.

After that public kufflele, the police made it their business to arrest Jack every time he went onto the course just to ruin his day because they felt like it. Jack lost his love for golf after this and he began drinking a little too much. He ran a small gambling den with his half-brother Tony Deorei after prohibition ended in 1933.

They opened the place in the West Loop area and in the end Jack ended up right back in the poorest sections of Little Italy where he begun his boyhood journey in Chicago. Tony was one of the two brothers that did get into the gang scene, but like this little gambling house, it was all smalltime stuff. With prohibition already over with, it wasn’t like there was mounds of cash to be made from bootlegging anymore.

 And this had a knock-on effect on illegal gambling as well. To make up for the loss of boxing and now golf, Jack picked up bowling. Predictably, he was pretty good at the game like he was at every other sport that he ever tried his hand at. But truth be told, Jack had lost his edge. That past attempt on his life that damaged his lung, kept causing him problems.

 The old scar had a habit of getting infected, forcing Jack to stop his religious commitment to his workout routine. His drinking was also getting worse, and he couldn’t control his mouth after a skinful, which predictably was starting to cause problems with his old friends. By 1936, Jack and Louise moved into a small apartment at 632 West Addison Street, which was a significant downgrade from his previous residences.

 And Jack was openly talking about getting back into the underworld scene. But Jack was now penniless and had fallen from grace. He was now also a crippling alcoholic, still reminiscing about the past and couldn’t accept the fact that he’d gone from one of the most feared men in Chicago to an average Joe in just 7 years.

 Struggling to let go of his glory days when drunk in the bars of Chicago, he liked to run his mouth about what he knew about Capone’s faction that none of the skeletons in the outfit was hidden from him. Frank Niti, Jack’s old foe within the outfit, took over from Capone when the old boss was sent to Alcatraz, and it became clear that his failing health was going to put him out of the game for good. And now he was in charge.

Niti’s patience was wearing thin. He had his hands full with the business of taking over the faction. And now Jack, whom he despised for years, was threatening to expose a great deal of sensitive information. Jack still had enough acquaintances left to be made aware of the fact that he was poking a bear.

 But that didn’t stop his drunken rants from happening. Jack just couldn’t let go of those golden years. Nor could he accept that a sleas ball like Niti in his eyes had taken over the greatest gang that the US had ever seen. Word must have gotten out that Jack was planning a comeback. Or perhaps Frank Niti had simply had enough.

 On February the 15th, 1936, the 7th anniversary of the St. Valentine’s Day massacre. Jack went out for a few games at the Avenue Recreations Bowling and Billiards Hall at 8:05 North Milwaukee Avenue. Witnesses say he arrived with two associates, men he clearly knew well, and greeted warmly. When they reached the second floor bowling alley, the receptionist handed Jack a Valentine’s Day card, expecting that someone had left it there for him.

 It had this cartoon printed on the cover of a destitute man and woman standing behind a for sale sign hawking their household goods. Inside was a cheeky poem written by hand. You’ve lost your job. You’ve lost your dough, your jewels and cars and handsome houses. But things could still be worse. You know, at least you haven’t lost your trousers.

 Jack tossed the Valentine’s card onto a bench and turned his attention to the game with his two friends. They had barely finished their first set when a third man stepped from the entrance, pistol in hand, ordering everyone to freeze. The two men who had walked in with Jack drew their weapons, too. A volley of shots rang out.

 Jack was hit several times, but it was the two rounds to the back of his head that sealed his fate. Machine gun Jack McGurn died where he fell. The man who once stood as Al Capone’s personal protector. The man who brought down the terrifying Haimey Weiss. The man who had survived countless ambushes, shootouts, and drivebys.

 The man who had orchestrated the militarystyle slaughter of the St. Valentine’s Day massacre that effectively ended the Chicago Beer Wars was dead. At just 33 years old, Jack lay broken, grizzled, and beaten down into poverty. his legendary face almost unrecognizable due to years of heavy drinking.

 Despite 20 witnesses, police had no physical evidence. That was until they found Jack’s Ford Lincoln sedan parked in front of 315 North Ada Street. The assassins had taken his car after the murder and used it as their getaway ride. In the two days that it was missing, they’d thoroughly cleaned it and left the keys inside. That ring of keys revealed a safety deposit box, but that was empty.

 Jack was truly and completely penniles when he died. He was buried at Mount Carmel Cemetery in Hillside, Illinois. At the funeral was a 6-ft tall floral arrangement with a banner that read from Al. Since Al Capone was still in Alcatraz, he sent his mother and sister to attend in hisstead. Louise cried bitterly at the funeral, but strangely enough, all of Jack’s siblings and his mother refused to acknowledge her at all.

 She had to stand on the other side of the coffin opposite from the family, indicating that they weren’t on speaking terms with her at all. Besides his halfb brotherther Anthony, in attendance, there were absolutely none of his former associates or friends to be seen. Even if there were any left who wanted to pay their respects, their new boss, Frank Niti, would have berated them for attending the Thorn in his sight’s final moments.

 Not to mention the dozen of police officers standing around the cemetery, hoping to catch any who were foolish enough to come out into the open. There were a few reporters waiting outside the gates, hoping to snap a picture or to get a quote from someone, and they weren’t disappointed. When they approached Anthony, Jack’s brother, to ask him if he knew who’d killed Jack, Anthony answered.

 He said, “I know the guys who killed Jack, and I’m going to get them.” 16 days after Jack’s murder on March the 2nd, 1936, Anthony was sitting at a card game at 103 Poke Street. He was reading the hand he was dealt when all of a sudden three men walked in. One stood guard at the door while the other two whipped out 38 caliber pistols and began unloading them into Anthony.

 Patrons of the pool room quickly took him to Mother Cabrini Hospital where he later died. He was just 24 years old at the time. And just like with Jack, there were no leads in the case. It could have been anyone who took out Jack and Anthony. The last of Iel’s men, maybe the final few Northsiders that remained active. Perhaps it was one of the hundreds of people connected to the dozens of murders he’d overseen and committed over the course of just a decade for El Capone.

 But probably it was men from the outfit, men that he knew, men that Frank Niti had sent to silence machine gun Jack once and for all. His mother, Josephine, who by 1936 had buried her husband, Angelo, and six of her sons, died just three years later at the age of 59. Jack’s childhood started out with a great deal of promise, a clean record, and multiple chances to become great in the ring.

 Jack had everything going for him. It was vengeance that drew this unassuming young man into a world of gangsters and made men who built their empires on bullets, booze, and blood that ruled the day. In less than 10 years, Jack went from squeaky clean to the most feared and prolific killer of the 1920s. Machine gun Jack was everything that embodied the era during his prime.

 But in less time that it took him to dominate the streets, he was reduced to a hollowed silhouette of the legend he once was, undone by the same world that he had once helped shape. Thanks so much for watching. Please like the video and consider subscribing if you enjoyed this tale of Machine Gun Jack.

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