The Real Jackie Flannery Wasn’t Fiction — He Was Worse – ht
April 25th, 1985, just after 11:00 in the morning, the corner of West 35th Street and 10th Avenue, in the shadow of the Javits Convention Center. Michael Holly was walking to work. Construction boots, lunch pail, a union card in his pocket. He never heard the car pull up behind him. He never saw the man in the black wig, the fake mustache, the oversized sunglasses covering a glass eye.
He just heard the first shot, then the second, then the third. Holly hit the pavement face down in broad daylight with witnesses on every corner, and the shooter calmly walked back to the getaway car like a man finishing a cigarette. The whole thing took 11 seconds. The shooter’s name was William Bokun.
Everyone in Hell’s Kitchen called him Billy. And what he had just done in front of morning commuters and hard hats and a Manhattan traffic cop two blocks away was exactly the kind of thing that made the Italian Mafia look at the Westies and think, “These people are out of their minds.” This wasn’t just another mob hit. This was a disguise in daylight on a public street, planned for eight years and executed like performance art.
Billy Bokun wore a wig because he wanted Mickey Featherstone, the Westies’ second in command, to take the fall. He wore the wig because Featherstone had red hair, and for a while, that plan actually worked. Featherstone was arrested. Featherstone went to trial. Featherstone was convicted of a murder he didn’t commit.
All because one Irish kid from West Side Manhattan wanted revenge for his older brother, and his crew went along with it, and the FBI couldn’t believe what they were watching. This is the story of the men who inspired Gary Oldman’s Jackie Flannery, the real Westies enforcers, the ones Hollywood had to tone down because nobody would believe them otherwise.
This is the story of Billy Bokun, Tommy Hess, and the man who stood behind them both, James Patrick Coonan, the Butcher of Hell’s Kitchen. This is how a handful of Irish kids from a 20-block stretch of Manhattan became so unhinged, so unpredictable, so willing to do the things nobody else would do that Paul Castellano himself sat them down in a restaurant on Mulberry Street and offered them a contract with the Gambino family.
But here’s what State of Grace never told you. Gary Oldman’s Jackie Flannery wasn’t one guy. He was a composite, a stitched-together ghost of three different killers. And the real men were stranger, sadder, and more dangerous than anything Sean Penn or Ed Harris could act around. You have to understand something right from the start.
The Westies didn’t rise because they were smart. They didn’t rise because they were organized. They rose because they scared the Italians, and in the world of organized crime, that is almost impossible to do. To understand Billy Bokun and Tommy Hess, you have to understand the neighborhood that made them, Hell’s Kitchen, the West Side of Manhattan between 34th Street and 59th Street.
40 blocks of tenements, docks, slaughterhouses, and Irish bars. In the 1960s and ’70s, it was the last piece of old New York that still belonged to working-class Irish Catholics. The piers, the Javits Center construction sites, the unions, the meat plants on 11th Avenue, and the man who ran all of it for decades was Mickey Spillane, not the writer, the gangster.
Mickey Spillane was the old-school boss of Hell’s Kitchen. He dressed well. He tipped the priests. He took care of widows. He pistol-whipped people instead of killing them. He was, by mob standards, a gentleman. Mickey Spillane had a kid in his neighborhood who was going to ruin all of that, [clears throat] Jimmy Coonan, born December 21st, 1946, to a middle-class Irish family on the West Side.
His father, John Coonan, was an accountant, not a criminal, not a gangster, a man with a calculator and a quiet life. But when Jimmy was 18 years old, something happened that broke the family forever. Mickey Spillane’s crew kidnapped John Coonan. They held him for ransom. They pistol-whipped him in front of his son.
They humiliated a man who had done nothing wrong in front of a kid who would remember every second of it. That was Mickey Spillane’s mistake because Jimmy Coonan didn’t forget. He didn’t forgive. He swore he was going to kill Mickey Spillane and everyone who stood next to him, and then he spent the next 12 years doing exactly that.
Coonan was a different animal than Spillane. Spillane was a throwback. Coonan was a monster in a leather jacket. He had a baby face, blond hair, blue eyes. Women thought he looked like a choir boy. And then he would walk into a bar on 10th Avenue and shoot somebody in the stomach for saying the wrong thing about his brother.
By the early 1970s, Coonan had a crew of young guys around him. They hung out at a bar called the Leprechaun Bar, later the Sunbright, later the 37th and 8th Bar. And one by one, the names of Spillane’s old lieutenants started showing up dead in the East River, in the trunks of abandoned cars, in pieces wrapped in garbage bags on the banks of the Hudson.
Here’s where it gets interesting. Coonan didn’t just kill his enemies, he disappeared them, and he learned how to do it from a man named Edward Cumiskey, Eddie the Butcher. Eddie Cumiskey was an old-school Irish hitman who actually worked as a butcher in a meat plant on the West Side. He had done time. He had killed people.
And he knew a professional’s trick that the younger kids had never heard of. If you cut up the body, there is no body. If there is no body, there is no murder charge. A missing person is a civil matter. A corpse is a homicide. Cumiskey sat Coonan down and taught him step by step exactly how to take apart a human being, where to cut, what to do with the hands because fingerprints identify, what to do with the head because dental records identify, what to freeze, what to burn, what to dump in the river.
Cumiskey called it doing a Hudson. >> [clears throat] >> And by 1976, Jimmy Coonan and his crew were doing Hudsons on a semi-regular basis. Mentor and student didn’t last long. Eddie the Butcher was gunned down in August of 1976 at the Sunbright Bar, but he had passed the technique to Coonan, and Coonan passed it to his crew, and that crew included a kid named Billy Bokun.
Billy Bokun was the one with the glass eye. You have to picture him. Slight build, dark hair, a face that was handsome on one side and off on the other because one eye didn’t move. He had lost the eye as a teenager in a street fight, and the fake replacement never quite tracked with the real one. So, when he looked at you, you couldn’t tell where he was looking.
It gave people the creeps. It gave the cops the creeps. And Billy leaned into it. He became the crazy one, the unpredictable one, the guy you didn’t want next to you at a bar because you couldn’t read his face. But Billy Bokun wasn’t crazy for fun. Billy Bokun was carrying a wound that went all the way back to March 25th, 1977.
That was the day his older brother, John Bokun, died. John Bokun was a Westy. John Bokun, along with a guy named Mickey Featherstone, had gone to a bar to shoot a man named Michael Holly. This was about a dispute. It was about respect. It was about the kind of thing that got people killed in Hell’s Kitchen every other week.
But there was an off-duty police officer in the bar that night. The off-duty cop saw John Bokun pull the gun, and the off-duty cop shot John Bokun dead, just like that. The older brother was gone. And Billy Bokun, who was still a kid, who had worshipped his brother, now had a reason to live, revenge. The Westies plotted to kill Michael Holly for eight years.
Eight years. Think about that for a second. The plans kept getting aborted. Holly would move. Holly would travel. The timing would be wrong. Somebody would get nervous. Coonan would push it back. But Billy Bokun never forgot. Every day for eight years, Billy got up and thought about the man who was responsible, in his mind, for his brother’s death.
And finally, in the spring of 1985, Jimmy Coonan gave the green light, and Billy got his revenge, and he did it in a wig. The details of that killing tell you everything about the Westies. Bokun and a crew member named Kenneth Shannon drove to the Javits Center construction site early that morning.
Bokun had dressed himself like Mickey Featherstone on purpose. The red wig, the mustache, the frame job was the whole point. Featherstone had been Billy’s brother’s friend. Featherstone had been there that night at the bar. And even though the cop was the one who killed John Bokun, somewhere in Billy’s mind, there was a belief that Featherstone should have protected him.
So, Billy decided, in the most Westies way imaginable, he would kill Michael Holly and send his own friend to prison for it. Two birds, one wig. The shooting took less than a minute. Holly went down on the sidewalk. Witnesses called the police. Somebody gave a description. Red hair, mustache, medium build. The cops went straight to Mickey Featherstone’s apartment.
Featherstone had been in New Jersey that morning at his mother-in-law’s house in Teaneck. He had an alibi. It didn’t matter. He was arrested. He was tried. He was convicted of murder in Manhattan Supreme Court, sentenced to 25 years to life. Featherstone sat in a prison cell for a murder he did not commit, set up by the little brother of a man he had once called his friend.
And that, more than almost anything, tells you why the Italians thought the Westies had lost their minds. But here’s what the history books don’t tell you. Featherstone getting framed was the beginning of the end, not the end of Billy Bokun, the end of Jimmy Coonan. Because when Mickey Featherstone realized his own crew had thrown him to the wolves, he made a decision that turned the FBI’s decade-long war into a slam dunk. He flipped.
Before we get there, though, we have to talk about Tommy Hess. Because if Billy Bokun was the revenge story, Tommy Hess was the cautionary tale. Tommy Hess was another Westie associate, a Hell’s Kitchen guy, part of that loose crew that floated around Coonan’s orbit in the mid-1970s. He drank at the same bars. He ran some of the same scams.
He was part of the scene. And like a lot of guys in that scene, he had a habit, heroin. In a crew where Jimmy Coonan was building discipline, creating a corporate-style Irish mafia, Hess was a liability. He used. He talked. He got sloppy. And in Hell’s Kitchen in the 1970s, being sloppy was a capital offense. Tommy Hess had a friend in the crew named Richie Ryan.
Richie Ryan was one of Coonan’s enforcers, cold-blooded, loyal, the kind of guy who didn’t ask questions when the boss pointed at somebody. And one night, for reasons that have been debated for decades, Richie Ryan walked into a Hell’s Kitchen bar where Tommy Hess was drinking. No warning, no argument. He walked up to his own friend, pistol-whipped him to the floor, and then shot him dead right there in front of the other patrons.
Tommy Hess was killed by the man he probably considered his closest associate. Because in Coonan’s Westies, that’s how it worked. Loyalty didn’t save you. Friendship didn’t save you. If Jimmy said you were a problem, you were dead before the words finished leaving his mouth. Tommy Hess is the ghost in Gary Oldman’s performance in State of Grace, the heroin, the erratic energy, the sense that this guy is doomed by his own neighborhood, that his own friends are going to have to put him down eventually. Oldman’s Jackie Flannery is
a man who everyone loves and nobody can save. That is Tommy Hess. That is the real story of a kid in Hell’s Kitchen who got addicted to the wrong drug in the wrong crew and couldn’t find a way out. And then there’s the top of the pyramid, Jimmy Coonan himself. The Jimmy Flannery character in State of Grace, Ed Harris’s role, is based loosely on Coonan.
But Coonan in real life was colder, smarter, and stranger than any movie has ever captured. By 1977, Coonan had what he wanted. On May 13th of that year, Mickey Spillane was shot dead outside his apartment in Woodside, Queens. The hit was done as a favor. A Gambino capo named Roy DeMeo, the same DeMeo who ran his own murder crew out of the Gemini Lounge in Brooklyn, handled it personally.
It had been 12 years since Spillane had kidnapped Coonan’s father. 12 years of waiting. 12 years of killing. And now the old king was dead, and the neighborhood belonged to a 30-year-old Irish kid with a baby face and a meat saw. Coonan’s next move was the one that made him legendary. He went to Mulberry Street. He went to Little Italy.
He sat down at the back of a restaurant with the most powerful Italian mobsters in New York City. 15 men, according to Featherstone’s later court testimony. Paul Castellano, Anthony Salerno, the boss of bosses and his top capos. And the Irish kid from the West Side made them an offer. He said, “Give us Hell’s Kitchen. Give us the piers.
Give us the construction unions, and we will do your wet work. We will do the hits you can’t do. We will be your Irish killers on call. All we ask is a piece of what flows through our neighborhood.” Castellano agreed. Why wouldn’t he? The Italians had a rule, no killing cops, no killing children, no killing family members.
The Westies had no such rules. The Westies killed anyone. The Westies cut up anyone. The Westies were a weapon the Gambinos had never had access to before. And in exchange for 10% of everything the Westies earned, Paul Castellano handed them a license to operate under Gambino protection. The Italian mafia and the Irish mafia in a formal alliance. It had never happened before.
It has never happened since. What made the Westies so valuable and so terrifying was the way they did business. You want to understand what made Billy Bokun and Tommy Hess and the rest of them different, you need to understand the Ruby Stein murder. Ruby Stein was a Jewish loan shark. He operated out of Brooklyn and Manhattan.
He was connected to the Genovese family. He was owed money by a lot of people, including Jimmy Coonan. Coonan owed Ruby Stein roughly $125,000 in 1977 money, which in today’s dollars is close to 700,000. Ruby Stein wanted his money. Jimmy Coonan did not have the money. So, Jimmy Coonan came up with a different plan.
The opportunity. Ruby Stein had a little black book. Every loan shark in New York had one. It listed every debtor, every amount, every interest rate. A working loan shark’s book in the 1970s could represent millions of dollars in outstanding debts. If you had Ruby Stein’s book, you owned Ruby Stein’s business. The inside connection.
Coonan invited Stein to the Cowboy Bar on 10th Avenue, a friendly meeting to talk about the debt, to work something out. Ruby Stein came alone. Ruby Stein trusted that the Westies, as crazy as they were, wouldn’t kill him over a loan. He was wrong. The execution. On May 7th, 1977, Jimmy Coonan shot Ruby Stein in the back of the head at the Cowboy Bar.
Then the crew got to work. They dragged the body into the back room. They stripped it. They cut off the fingers and the head. They used Eddie Cummiskey’s technique. They put the pieces into garbage bags. They loaded the bags into cars. They drove to the Hudson River piers and started throwing pieces into the water. The money.
Coonan took Ruby Stein’s book. Overnight, every debt Ruby Stein had been collecting became a Westies debt. Coonan sent his guys to the customers and said, “You used to pay Ruby. Now you pay us.” The transition was seamless. By one estimate, Coonan took over roughly $2 million in outstanding loan book in a single afternoon for the cost of a few bullets.
The problem. The Westies were good at killing. They were not good at disposing. When they cut up Ruby Stein, they forgot one detail. They didn’t puncture the lungs. In professional body disposal, you puncture the lungs so the corpse sinks. Ruby Stein’s torso, without lungs punctured, floated.
Four days later, a fisherman off the Rockaways hooked what he thought was a bag of trash. It was Ruby Stein’s upper body, washed up whole, still wearing his belt. And suddenly, every detective in New York knew that the Westies had killed a Genovese-connected loan shark, and the war was on. That was Jimmy Coonan.
And that was the environment that produced Billy Bokun, Tommy Hess, and every other maniac in the crew. Bodies in bags. Bar shootings in broad daylight. Disguises with wigs. Family members killing family members. The Italians would sit at their tables on Mulberry Street and shake their heads. These Irish kids didn’t plan. They didn’t think. They just reacted.
And the reactions were getting messier every year. The other murder that tells you everything is the Ricky Tessielo killing. Richard Tessielo was a gambling addict. He was a small-time hustler in Hell’s Kitchen. He owed money to Westies loan sharks. He couldn’t pay. His own brother actually went to Coonan and said, “Do whatever you have to do.
Just teach my brother a lesson.” That is Hell’s Kitchen. That is a neighborhood where a man turns over his own sibling because the debt is becoming a family embarrassment. Coonan had Tessielo brought to an apartment. Featherstone was there. Bokun was there. Other crew members were there. Coonan shot Tessielo in the head.
And then, according to later court testimony, the crew dismembered him in the apartment, in the bathtub, over a period of hours, the body parts went into bags. The bags went into the river. The body was never recovered. When Mickey Featherstone finally testified, years later, he told the jury that he had helped with the murder, but had refused to help cut up the body.
He said he sat in the kitchen. He said he couldn’t do it. He said Coonan came out later covered in blood and washed his hands in the sink and asked Featherstone what he wanted for dinner. That’s the detail that sticks with you. The most reliable killer in the Westies said on the witness stand, “I killed for them, but I couldn’t cut.
” And the boss asked me what I wanted for dinner. By the early 1980s, the Westies were at the peak of their power. They had Gambino protection. They had the piers. They had pieces of the concrete industry. They had loan books. They had bookmaking. They had extortion rackets across 40 blocks.
They had somewhere between 15 and 20 hardcore members, and maybe another 50 associates. And they had done, by FBI estimates, between 60 and 100 murders over the decade. But here’s where it gets interesting. That kind of violence attracts attention. And by 1985, the attention was becoming a problem. The Michael Holly hit was the mistake.
Billy Bokun’s revenge, 8 years in the making, turned out to be the single dumbest thing the Westies ever did. Because when the cops arrested Mickey Featherstone for the Holly murder, they did what cops always do with a suspect. They leaned on him. They told him he was looking at life in prison. They told him his wife and kid would be alone.
And Featherstone, sitting in jail for a murder he didn’t commit, began to realize something. He wasn’t looking at a mistake. He was looking at a setup. His own crew had done this to him. Featherstone’s wife, [ __ ] figured it out first. She got word to Featherstone in jail through his lawyers. It was Bokun. It was the wig. It was the frame job.
And when Featherstone put it all together, something inside him broke. He had killed for these guys. He had taken risks for these guys. He had spent his whole life for these guys. And now one of them had sent him to rot for a killing he didn’t even commit. In 1986, Francis Mickey Featherstone picked up a phone and called the FBI.
And he told them he was ready to talk. This was the end. Featherstone knew everything. He knew the Ruby Stein murder. He knew the Tassiello murder. He knew who had killed Mickey Spillane. He knew the arrangements with the Gambino family. He knew where bodies had been dumped and whose bodies they were. He had been inside the room for almost every major moment in Westies history for 10 years.
And now he was handing it all, piece by piece, to the federal prosecutors in the Southern District of New York. The RICO indictment came down on March 10th, 1987. 10 defendants. Jimmy Coonan, his brother Jackie Coonan, Billy Bokun, Kevin Kelly, Kenneth Shannon, Jimmy McElroy, Richie Ryan, and others.
The charges included 14 separate acts of murder, attempted murder, kidnapping, loan sharking, extortion, gambling, and narcotics trafficking. It was, at the time, one of the most comprehensive organized crime prosecutions in New York history. The trial began in October of 1987 and lasted more than 4 months. Mickey Featherstone was the star witness.
He sat on the stand for weeks. He told the jury about the Ruby Stein murder. He told them about the Tassiello dismemberment. He told them about the Mulberry Street meeting with Castellano. He told them about Billy Bokun’s wig. And on February 24th, 1988, the jury came back with a verdict. Seven defendants were convicted of racketeering.
Jimmy Coonan was convicted of racketeering and multiple murders. He was sentenced to 75 years in federal prison. Billy Bokun’s case took a different path. He was initially acquitted on some of the federal charges. But the state came after him separately for the Michael Holly murder. He was indicted by the Manhattan District Attorney in 1987.
He fought the case for years. Eventually, under pressure, in 1995, the Second Circuit addressed part of his appeal. Billy Bokun would spend years of his life fighting charges connected to the wig, the disguise, the 8-year revenge plan for his brother. The frame job had come back on him. Tommy Hess never lived to see any of it. Richie Ryan had killed him years before in that Hell’s Kitchen bar for the crime of being an addict in a crew that couldn’t afford weakness.
Tommy Hess is a name in the files, a body in the record, a kid who became a statistic because his own best friend was willing to pistol-whip him and shoot him in front of witnesses and walk out of the bar like nothing had happened. What happened after? Mickey Featherstone went into the federal witness protection program. He was relocated.
He was given a new name. He has given interviews over the years. He has lived, as of the last confirmed reports, a quiet life far from New York. The man who almost went to prison for a murder committed by his own friend is the man who, in the end, brought the whole house down. >> [clears throat] >> Jimmy Coonan spent decades in federal prison.
He was eligible for release after serving most of his sentence and has largely disappeared from public life. Billy Bokun, the kid with the glass eye who loved his brother so much he killed a man in a wig, was eventually convicted at the state level for the Holly murder. He did hard time. He walks with the reputation, to this day, of being one of the most unhinged shooters in American organized crime history.
Here’s what’s worth sitting with. Gary Oldman took those three men, Billy Bokun’s revenge, Tommy Hess’s addiction, Jimmy Coonan’s ice-cold leadership, and melted them into one character in State of Grace, Jackie Flannery, the wild one, the unpredictable one, the one you cannot control and cannot save. Oldman understood something about the Westies that the screenwriter, Dennis McIntyre, had captured on the page.
These guys were not cool. These guys were not glamorous. These guys were damaged children in grown men’s bodies, running a 40-block stretch of Manhattan on pure rage, pure loyalty, and pure grief. The Westies as a functioning crime family ended with the 1988 convictions. 40 years later, Hell’s Kitchen looks nothing like it did then.
The tenements have been replaced by luxury high-rises. The piers are office parks. The meat plants are restaurants. The Javits Center, where Billy Bokun shot Michael Holly in broad daylight, is now surrounded by glass towers and overpriced hotels. The kids who grew up on those streets in the 1970s are either dead or in prison or old men living on social security in apartments their grandfathers once owned.
But the Westies left a legacy that people in law enforcement still talk about. They were the proof that an ethnic crime group could force itself into the Italian Mafia’s orbit without actually becoming part of it. They were the proof that violence without structure could still generate tens of millions of dollars.
They were the proof that the most dangerous gangster is not the one with the plan. It is the one who doesn’t care about the plan. The one who will shoot you in a bar in front of witnesses. The one who will cut up your body because he forgot to puncture your lungs. The one who will wear a wig in the daylight and frame his own best friend.
And here’s the final thought. Every movie about the Mafia tells you the same lie, that organized crime is a business, that these are professionals. That the violence is surgical and the decisions are strategic. That is Michael Corleone. That is Tony Soprano. That is the fantasy the industry sells. But the Westies were the truth.
The Westies were what actually happens when you hand a gun to a kid whose father was pistol-whipped. A kid whose brother was shot by a cop. A kid who grew up in a neighborhood where nobody trusted the outside world and everybody owed somebody money. You don’t get The Godfather. You get Billy Bokun in a wig.
You get Tommy Hess on a barroom floor. You get Ruby Stein’s torso floating in the Rockaways because somebody forgot a simple step. That’s the real Jackie Flannery. That’s the real Westies story. Not a movie. Not a myth. Just a neighborhood full of broken men who made the Italian Mafia look civilized by comparison and then spent the rest of their lives in federal cells or unmarked graves, waiting for a redemption that was never going to come.
Because in Hell’s Kitchen, in the 1970s and ’80s, the only thing more dangerous than your enemies was the man sitting next to you at the bar. And Billy Bokun, Tommy Hess, and Jimmy Coonan proved it every single day until the FBI and the jury and the years finally brought the whole thing down. If you found this story fascinating, hit subscribe.
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