The unglamorous life of Three-Finger Jack

0:00What's up, baby? It's Brettzki. And I'm here to tell you that SpinQuest.com is giving out free sweeps coins. All you got to do is purchase a $10 coin pack. And guess what? They're going to give you the coins from a $30 coin pack. That lets you play all your favorite games like Blackjack, Wanted Dead or Wild, and we're talking real cash prizes, baby. SpinQuest.com SpinQuest is a free-to-play social casino. Boydware prohibited. Visit SpinQuest.com for more details. Have you ever caught yourself watching one of those slick 1930s gangster movies? Oh, you mean the ones with the tailored pinstripes suits? Yes, exactly. The suits and the Fedora's tilted just right. Right, where the mastermind criminals are executing these flawless clockwork bank heists. And they just look effortlessly cool and untouchable the whole time. I know exactly the vibe we're talking about. Well, today we are going to grab that polished Hollywood veneer and peel it right back. We really are. Because our mission for this deep dive is to look at the gritty and chaotic

1:02and frequently botched reality of a life of crime. Specifically during the infamous public enemy era. Right. And our source material for this journey is a highly detailed Wikipedia article chronicling the life and the incredibly bizarre death of John Hamilton. Also known as Red Hamilton. Yes, Red Hamilton, a Canadian-born gangster from the 1920s and 30s. And a key heavy hitting associate of none other than John Dillinger. It's so great to have you here to dig into this. It is great to be diving into this with you. Where should we start? Well, to really set the mood for our analysis today. I want you to imagine the visual backdrop for our discussion. Okay, and picturing it. Picture a classic 1930s style police evidence board right behind me. Oh, like the cork boards with the push pins. Exactly. We're talking grainy black and white mug shots pinned to the board. Lots of newspaper clippings with those blaring sensational headlines. And a chaotic sprawling web of red string. Connecting all the various bank heists and shootouts.

2:02And the hideouts, scratching all across the American Midwest. That visual really puts you right in the shoes of the detectives trying to track this guy down. It does. Because I want you to imagine what it really takes to become a public enemy. It's not what the movies show. No spoiler alert right out of the gate here. It is mostly just sheer panic. Terrible split second decisions. And a whole lot of running in the dark. So true. So let's start at the very beginning. Who is the man behind the mug shot? Let's get into his origins. John Hamilton was born on August 27, 1898, up in Bing in Lit, Ontario. To an Irish Canadian father and a German American mother. Which is a rather unassuming origin point. It really is. When we analyze the great American gangsters of the 1930s, we don't typically picture a kid from a small logging community in Ontario. Right, you think of Chicago or New York. Exactly. But his story moves south of the border pretty quickly. And that's where the mythology really begins to take shape.

3:03The nickname start flying. Oh, yeah. Before he even really get started in his major criminal career, he picks up one of those classic, distinctly underworld nicknames. The papers call them three finger jack. Now you might assume you got a name like that from some gritty underworld torture session. Or a bank vault door slamming on his hand during a getaway. Right, that sounds so cinematic. But nope. No, he lost two fingers on his right hand in a childhood sledding accident. A sledding accident. Just a normal winter kid thing gone wrong. It is a stark reminder of the era long before modern safety standards were advanced reconstructive surgery. Yeah, that. But from an operational standpoint that missing pair of fingers on his dominant hand would become his most defining physical characteristic. And as we'll see later when we look at the pop culture surrounding him, it makes some of his Hollywood portrayals quite amusing. We will definitely get to the Hollywood treatment. But let's jump to the turning point in his life. The moment that really solidifies his path into the underworld.

4:03March 1927. Right. Hamilton gets busted for robbing a gas station in Indiana. Just a single run of the mill gas station. And for that crime, he is slapped with a staggering 25 year prison sentence. It's 25 years. It's wait a quarter of a century for a single gas station. And I know. That seems wildly disproportionate, doesn't it? What's fascinating here is how that incredibly harsh, seemingly punitive sentence completely backfired on the justice system. How so? Well, the intention presumably was to lock a petty thief away for good and protect society. Sure. Keep him off the streets. But instead of rehabilitation or even just basic deterrence, the Indiana State Prison effectively function as an elite networking event for the criminal underworld. Oh, wow. So they basically locked him in a concrete box with the worst people imaginable and hoped for the best. That is the tragic irony of the penal system at the time. Yeah. The state's attempt to isolate him actually gave him the exact infrastructure he needed

5:04to build a supergang. By throwing Hamilton into that specific environment in Michigan City for two and a half decades. The state guaranteed he would rub shoulders with the most ambitious criminals of his generation. While incarcerated Hamilton befriends absolute heavy hitters. We're talking about John Dillinger. Russell Clark. Charles Makley. Harry Pierpont. And Homer Van Meter. This wasn't just a group of inmates passing the time. Not at all. This was the incubation of a massive criminal enterprise. It's like the Avengers, but for robbing banks. That is a perfect way to put it. And they formed an incredibly tight bond in there. They really did. And Dillinger actually ends up getting paroled first in May of 1933. But he doesn't just walk away, get a legitimate job and start a new life. No, he swears to liberate his friends. So Dillinger orchestrates this massive highly coordinated smuggling operation from the outside. Getting handguns sneaked right into the prison. For Hamilton Makley, Pierpont Clark and the others. Which all culminates on September 26th, 1933. With a massive 10-man escape right out of the main gate of the Indiana State prison.

6:09Walking out of the main gate of a state penitentiary is a brazen operational success. It sounds impossible. It requires inside help, immense coordination and sheer nerve. But the victory is incredibly short-lived. Because the landscape shifts almost immediately upon their exit. The newly freed gang quickly learns that their benefactor Dillinger had been busy on the outside. Very busy. He was arrested for bank robbery. And is now sitting in a cell in Lyma, Ohio. So Dillinger broke them out and now they have to return the favor. But jail breaks are not cheap. No, you need fast getaway cars, safe houses, bribes, and heavy weaponry. How do they pull together the capital for a rescue operation? They do what they do best. On October 3rd, 1933, Hamilton and the gang roll into St. Mary's, Ohio and rob a bank. And they walk away with $14,000. Which is pushing $348,000 in 2025 money. A massive war chest. And without immediate influx of cash, they execute the Lyma jailbreak just nine days later.

7:09On October 12th, 1933, Hamilton accompanies Charles MacLeigh, Harry Peerpont, Russell Clark, and Ed Shouse to free Dillinger. But there is a very crucial detail we need to point out here about the Lyma jailbreak. Right. While MacLeigh and Peerpont burst into the building and end up murdering Sheriff Jess Sarber during the escape. Hamilton actually stayed outside. He didn't enter the jail and he did not participate in the shooting of the sheriff. That is a distinction that matters in a courtroom. But out on the street in the eyes of the law enforcement community, they were all painted with the exact same brush. The gang was now officially responsible for the death of a law man. And that fundamental shift escalates the manhunt. They aren't just hunting bank robbers anymore. They are hunting cop killers. The rules of engagement completely change. And the escalation just keeps ramping up. By December 1933, the gang is feeling absolutely untouchable. They execute an armed invasion of a Chicago bank, specifically targeting the safe deposit boxes. They walk away with $50,000, which today would be about $1.24 million.

8:13They are flush with cash. Everything is going perfectly until until a massive mistake. Okay, let's unpack this. The absolute absurdity of how a multi-million dollar gang gets tripped up. It's almost hard to believe. Hamilton decides to leave his car at a Chicago garage to get some bodywork done. Considering the heat on them bringing a vehicle linked to an underworld syndicate into a public garage for cosmetic repairs. It is a staggering lapse in judgment. It really is. The mechanic at this garage takes one look at the vehicle, gets suspicious of what he literally calls this gangster car, and decides to call the cops. So Hamilton strolls back to the garage to pick up his ride, probably expecting to just pay his bill and drive off. And instead, finds Detective William Shanley and two other officers waiting for him. Hamilton doesn't hesitate. He opens fire. He kills Detective Shanley right there at the garage, and somehow manages to completely elude the other two officers and escape into the city. If we connect this to the bigger picture, this specific incident at the Chicago garage

9:14is a watershed moment in criminal history. Oh, so. We are seeing the death of the local reactive police force and the birth of the modern proactive dedicated task force. So Hamilton didn't just kill a cop. He inadvertently forced law enforcement to modernize. Exactly. The systemic reaction to the murder of Detective Shanley forces the Chicago police department to form a dedicated 40-man Dillinger squad. Sully focused on taking them down. 40 cops with one singular job. The walls are really starting to close in. And it leads to even more chaos. On January 15th, 1934, Hamilton and Dillinger hit a bank in E Chicago, Indiana. Grabbing over $20,000. But it's an absolute bloodbath. Police officer William O'Malley is killed. Now, Dillinger is officially charged with O'Malley's murder. But multiple witnesses on the scene point the finger directly at Hamilton, saying he was the actual shooter. And Hamilton doesn't walk away clean either. He takes two bullets during this heist. So the pressure on the syndicate is now immense.

10:14The sheer volume of law enforcement resources dedicated to finding them makes large group movements impossible. The gang realizes they are too hot to stay together. So they make the strategic decision to scatter. Dillinger and several others head down to Tucson, Arizona. Where they are subsequently apprehended. Right, they get caught. Meanwhile, a badly wounded Hamilton goes deep underground. He's left in the carrow's girlfriend Pat Charington. And an underworld physician by the narrative Joseph Moran. And with Dillinger behind bars in Arizona, Hamilton briefly rockets to the very top of the public enemy's list. He is the number one most wanted man in America. But that ranking only lasts until Dillinger pulls off his legendary escape from Crown Point. Dillinger gets out, tracks down Hamilton, and they put together a brand new gang. And listen to this roster. You've got Hamilton, Homer, Van Meter, Tommy, Carol, Eddie Green, and the notoriously unhinged babyface Nelson. It is certainly a formidable lineup on paper. But the operational discipline of the original gang is completely gone.

11:16They embark on a string of robberies that are lucrative, but incredibly messy. The meticulous clockwork planning we associate with these heists is replaced by sheer violence, paranoia, and desperation. Here's where it gets really interesting because the universe just starts throwing absolutely wild curveballs at them. Just absolute chaos. Let's look at their hit and suitfalls. Babyface Nelson spots a motorcycle cop named Hail Keith and shoots him right through a plate glass window. Just senseless violence. And then they try to hit a bank in Mason City, and you will not believe this. What happened? Hamilton gets shot in the shoulder again, but not by the 40-man Dillinger squad. Not by the FBI. He gets clipped by an elderly judge who happened to be looking out his window across the street and just decided to open fire on the gang. An elderly judge. From across the street, Dillinger is wounded in that same shootout, too. The visual of a highly armed supergang being pinned down by a senior citizen from across the street perfectly illustrates the total breakdown of their operational security.

12:18They aren't just fighting law enforcement anymore. The entire public is turning against them. They're bleeding, they are exhausted, and they have absolutely no safe harbor. So on April 17th, 1934, Hamilton and Dillinger make a desperate discrete visit to Hamilton's sister. Up in Salt St. Marie, Michigan. They're just trying to find a friendly face and catch their breath. After that, the gang retreats to a place called the Little Bohemia Resort deep in the woods of Wisconsin. They were looking for sanctuary and isolation, but they walked directly into a trap. On April 22nd, the resort is rated by the FBI. The operation is directed by the famous Melvin Purvis. The Bureau had received a tip from a friend of the resort's owner. But the execution of this raid was a complete tragedy of errors. He was an absolute disaster. The FBI approached the resort in the freezing dark. Tensions were incredibly high. And in that tense paranoid atmosphere, the agents mistakenly opened fire on a car pulling away from the lodge. But it wasn't the gangsters in the car.

13:19It was three local work camp employees. The FBI kills a man named Eugene Borno and severely wounds John Hoffman and John Morris. Just innocent guys leaving a lodge who got caught in the crossfire of this massive federal manhood. And while the FBI is busy shooting at the wrong people, the actual gang inside realizes what's happening. And the escape they make is something out of a nightmare. Dillinger, Hamilton, Van Meter, and Tommy Carroll have to leap from a second floor back window. Imagine the physical agony of that. They land on a mound of frozen snow in the dead of winter, scrambling into the freezing darkness while nursing fresh bullet wounds. They run along the shore of Star Lake desperate to get away and finally managed to steal a car from a local carpenter about a half mile down the road. They survived the night, but the sheer physical toll of jumping from windows and running through the freezing Wisconsin woods was immense. And their luck had finally run out. Just one day later, on April 23rd, another shootout occurs. In Hastings, Minnesota. Another town, another shootout.

14:20This is the final one for Three Finger Jack. As they are fleeing in the escape car, Hamilton takes a mortal wound. He's dying in the back seat. So they drive him all the way back to Chicago back to that underworld doctor, Joseph Moran. The same guy who patched him up just a few months prior. But this time, Moran takes one look at Hamilton and completely refuses to treat him. For reasons unknown, he just turns them away. He leaves him to die. So Dillinger is stuck with his dying friend in the back seat of a car. Dillinger along with Voney Davis and Edna Murray hide Hamilton in Aurora, Illinois. And there, over the course of a few agonizing days, John Hamilton dies on April 26th. Dillinger and Davis take the body out near as we go, Illinois, and bury their friend. And to make sure the cops can identify him if he's found, they cover Hamilton's face and hands with lie. A brutal, undignified end to a brutal life. It really is. But the narrative doesn't actually end with his burial. So what does this all mean? It means the authorities were completely in the dark about his demise.

15:21The federal government is spending vast amounts of money and resources hunting a ghost. Almost three weeks after he was buried in that lie-covered grave on May 19th, the government officially indicted him. And it gets even more bizarre. His sister, the one they visited up in Michigan, was actually convicted of harboring a fugitive. And spent time in prison, all while her brother was already riding in the ground. And because his death was kept secret by the gang, rumors began to swirl that Hamilton had actually survived the hasting shootout. It became an urban legend almost immediately. The FBI got countless tips from people claiming they saw him. Even Hamilton's own nephew stubbornly maintained that he had personally visited his uncle back in Ontario. Long after the supposed date of his death. But eventually the truth always comes out. Dental records proved the body in Oswego was indeed three-finger jack. They matched the Amalgam restorations, which are essentially his silver cavity fillings on the teeth of the corpse. With the dental records from his time at the Indiana State Penitentiary.

16:23Yet despite the grim, verified, and heavily documented reality of his life and death, popular culture couldn't resist reshaping his story. Oh, Hollywood absolutely loves playing fast and loose with history. We talked about this at the beginning. Yes, Hamilton pops up in a bunch of media over the decades. He's featured in the 1957 movie Babyface Nelson. Stephen King even wrote a short story about his final days called The Death of Jack Hamilton. But my absolute favorite piece of pop culture and accuracy is the 2009 film Public Enemies. What did they get wrong? Actor Jason Clark plays Hamilton. He's up there on the big screen holding Tommy guns driving the getaway cars. And let me guess he has all his fingers. He very clearly has all five fingers on his right hands. They completely ignored the whole three-finger jack moniker. They entirely ignored it. It is a perfect metaphor for how we sanitize history. We want the aesthetic of the roaring 30s gangster without the gritty missing finger reality. Exactly. And that is exactly why we do these deep dives because pop culture loves to romanticize these outlaws

17:25as smooth calculated operators. But the reality was a brutal chaotic series of botched raids. It was friendly fire, getting shot by elderly judges and dying a slow secret death. Before we wrap up today, I know you had one more piece to add. I want to leave you with a final concept to mull over that wasn't previously discussed. You had. Consider the collapse of the underworld ecosystem. What do you mean by that? When a criminal becomes so infamous, so highly targeted that even the mob's own secret doctor. And the very people who profit off this violence. Refuse to treat them and leave them to die. What does that say about the absolute isolation of being a public enemy? Wow. At the very top of a criminal food chain, there is zero loyalty only self-preservation. That is such a chilling point to end on. The absolute isolation of it all. It really reframes the whole gangster lifestyle. Thank you so much for joining us on this deep dive into the chaotic life of John Hamilton. It was a pleasure to unpack it all. We hope we've given you a new perspective

18:26on the reality behind the myth. Until next time, keep questioning the story and stay insanely curious. I'm here with SpinQuest, where you can play and win from the comfort of your own home with hundreds of slot games and all of the table games you love with real cash prizes. Right now, $30 coin packs are on sale for $10 for new users. It's all at spinquest.com. That's S-P-I-N-Q-U-E-S-T dot com. SpinQuest is a free to play social casino. Boyed where prohibited, visit SpinQuest.com for more details. Every day, excessive delays and denials from big insurers keep patients from accessing the care they need. And when care is urgent, these delays can be disastrous. These practices cost billions in wasteful spending, driving up costs for American families. But while big insurers put up barriers, America's hospitals and health systems are in your corner, navigating endless reviews and appeals to get you the care you need when you need it most. It's time to curb these harmful practices

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