January 6th, 1995. Boca Raton, Florida. A condominium complex off Glades Road. The kind of place retirees go to disappear into the palm trees. 6:00 in the morning. The sky was still that bruised purple color you only see in South Florida before sunrise. Federal agents in tactical vests moved through the parking lot in a single file line. Weapons drawn.
They surrounded unit 204. The man inside was 54 years old. He was making coffee. He was wearing a bathrobe. He had been a fugitive for 16 years, 4 months, and 11 days. When the agents kicked the door, he didn’t run. He didn’t reach for a weapon. He turned around slowly, put his hands behind his head, and said one sentence. “You guys took long enough.
” The man in the bathrobe was John Vincent Marterano. By his own confession, he had killed 20 people. He would serve 12 years. 12 years for 20 lives. Do that math. 7 months per body. Today he walks free in Massachusetts. He sells real estate. He gives interviews. He had dinner with the producers of Black Mass.
This wasn’t a mafia capo. This wasn’t a maid man. Marano was something stranger and more dangerous. Half Italian, half Irish. The only Italian to ever ride for the Winter Hill gang. He was Howy Witter’s enforcer. Then he was Whitey Bulgers’s personal hitman. He killed for free.
He never took a contract payment in his life. He called himself a vigilante. The FBI called him a problem they couldn’t solve. The victim’s families called him something else entirely. This is the story of how a kid from the north end of Boston became the most prolific Irish mob killer in American history. how the FBI’s own informant program protected him for 20 years, and how a single state dinner in a federal holding cell brought the entire operation crashing down.
From the playgrounds of East Milton to the runway at Tulsa International Airport, this is the rise, the rain, and the reckoning of the man they called the executioner. But here’s what Black Mass couldn’t tell you in 2 hours of screen time. Johnny Marano didn’t just kill for Whitey Bulier. He killed because he believed Whitey was the only honest man in the room.
And the moment he learned the truth, the entire Boston underworld collapsed in on itself. To understand Johnny Marterano, you have to understand Boston in the 1940s. Born December 13th, 1940 to Andrew Marterano, a hard-working Italian immigrant who ran Luigi’s restaurant in the North End and a tough Irish mother from the neighborhoods of Somerville.
Two worlds, two tribes, two ways of seeing the city. In Boston back then, you were one or the other. You weren’t both. Johnny was both. And from the time he could walk, that made him an outsider in two communities at once. The Italian kids didn’t trust the half-Irish boy. The Irish kids saw the Italian last name and remembered every grudge from the old country.
So Johnny did what outsiders always do. He learned to fight. By age 12, he was the biggest kid in his class at Milton High. By 15, he was running with a crew of older boys who hung around the pool halls on Dudley Street. By 17, he had already done his first stint in juvenile detention for assault. He was, by every account, charming, quiet, polite to your mother, and absolutely willing to put a man in the hospital over a $5 debt.
His younger brother, James, was different. James was the good son, the college boy. Johnny was the one who took the calls his father didn’t want to know about. By the time he turned 21, Johnny was working as a bouncer at a club called Basin Street South in the South End. And he was making money on the side, running a numbers operation and collecting for a lone shark named Phil Wagenheim.
This is where his story really begins. Because at Basin Street sometime in 1964, Johnny Marterano met two men who would change his life forever. The first was Howie Winter, a stocky, soft-spoken Irish kid from Somerville who was already running the rackets in the Winter Hill section of town.
The second was a wiry, intense, sharpeyed kid from Souy named James Bulier. They called him Whitey because of his platinum blonde hair. You have to understand something. In 1964, Boston, you didn’t cross tribal lines. The Italians ran the north end under the Patriarcha family out of Providence. The Irish ran souy Charles Town and Somerville. They didn’t work together.
They killed each other. So when Howie Winter looked at this big halfallian kid from Milton and said, “I don’t care what your last name is, kid. You ride with us.” That was a moment that should not have happened. But Johnny Marterano rode. And from 1965 onward, he was Irish. The first killing came in 1965. A small-time hustler named Robert Paladino had insulted Johnny’s friend at a bar. The accounts vary on this.
What’s documented is that Paladino’s body was found. Johnny was 19. He never spoke of it on the record until 40 years later in a federal courtroom when he confessed under oath. He said it didn’t bother him then. He said it didn’t bother him now. By 1969, Johnny had killed at least four more men.
The Boston Irish gang wars of the late60s were the bloodiest in American history outside of prohibition. The Mlan faction in Somerville and the Mlaughlin brothers in Charles Town were exterminating each other over an insult that happened at a Labor Day picnic in 1961. 60 men died in those wars. 60. Johnny Marano fought on the winter hillside.
He didn’t pick the side because he believed in it. He picked it because Howie Winter treated him like a brother. Here’s where it gets interesting. By 1972, the wars were over. Howie Winter had won. The Winter Hill gang now controlled every Irish racket in the Boston area. bookmaking, lone sharking, truck hijackings, horse race fixing.
And sitting at the top of the operation, with Howie at his right hand and Johnny as his enforcer, was a coalition of men who had just survived a war that killed everyone they grew up with. They were rich. They were paranoid. And they were about to make the worst decision of their criminal lives.
They were about to let Whitey Bulier into the inner circle. Remember that name, Whitey Bulier. He will become important very soon. Because in 1975, while Johnny Marterano was running the day-to-day muscle for the gang, Whitey Bulier walked into a parking lot in Quincy and met with a man named John Connelly.
Connelly was an FBI agent. He had grown up in the same souy housing projects as Whiteidy. And on that day in 1975, Whitey Bulier became top echelon informant number BS1444. The FBI now had a rad at the heart of the Winter Hill gang. And nobody knew it. Not Howie, not Johnny, not the men who had bled for the operation for 10 years.
The FBI was about to weaponize that secret in ways that would protect Bulier and Steven Flemmy for the next 25 years. while Johnny Marterano did the killing. The first beneficiary of the new arrangement was a man named Roger Wheeler. But to get to him, you have to understand the horse race fixing scheme that put Johnny in the middle of a federal investigation in the first place.
In 1974, the Winter Hill gang had perfected a scheme called the boat race. Here’s how it worked. They identified jockeyies at small tracks in New England, New Jersey, and Atlantic City who were carrying gambling debts. They paid the jockeys $5,000 per race to throw the outcome. They knew which horses would lose, so they bet heavily on the long shots.
In a typical week, the gang would clear $100,000 in winnings, sometimes more. They were running this scam at 20 different tracks across six states. The problem was a man named Anthony Cula. He was the inside man on the jockey side. He got pinched in 1977 and he flipped. He named names. He named Howie Winter. He named Johnny Marterano.
And in 1979, federal indictments came down for race fixing. 21 defendants. But two names were missing from the indictment. Whitey Bulier and Steven Fleming. Their handler, John Connelly, had them removed. The official reason on paper was insufficient evidence. The real reason was that they were informants. Johnny didn’t see it.
Howie didn’t see it. They thought Whitey and Stevie had just gotten lucky. Howie went to prison. Johnny went on the run. And before he disappeared into Florida, he handed the entire Winter Hill operation to the two men he trusted most in the world. Whitey Bulier, Steven Flemmy. He gave them everything. The bookmakers, the territories, the loan customers, the connections.
He told them, “Take care of business. I’ll be back when this blows over.” That was 1979. He wouldn’t be back for 16 years. But before he left, there was one more job. World High, a company that operated highly frontends in Florida and Connecticut. Massive cash business, the kind of operation that processed millions of dollars in legal gambling every week.
The Winter Hill gang had been skimming from World High for years through a contact named John Callahan. Callahan was an accountant, a Boston College graduate, a man who wore expensive suits and loved hanging around tough guys. He worked at the company as a treasurer. He was their inside man. But in 1981, World High was sold to a Tulsa, Oklahoma businessman named Roger Wheeler.
Wheeler was clean, a self-made millionaire, Christian, conservative, father of four. He took one look at the company books and saw money was missing. Lots of money. He started asking questions. He hired auditors. He fired Callahan. and he made it clear he was going to follow the trail of the missing cash wherever it led.
The trail led directly to Whitey Bulier and Steven Flemmy in Boston through Callahan who knew everything. This is when Whitey Bulier made the call. He called Johnny Marterano who was hiding in Florida under a false name. He asked Johnny to come back for one job. Roger Wheeler had to die. Callahan had vouched that Wheeler had become a problem that couldn’t be solved any other way. Johnny agreed.
He didn’t ask questions. That was his code. If Whitey said it needed to be done, it needed to be done. May 27th, 1981. Tulsa, Oklahoma, Southern Hills Country Club. Roger Wheeler had just finished 18 holes of golf. It was 4:00 in the afternoon. He walked across the parking lot to his Cadillac.
He opened the driver’s side door and sat down. Johnny Marterano walked up to the window. He fired one shot into Roger Wheeler’s face from a distance of less than 3 ft. Wheeler died instantly. Johnny walked away. He flew back to Florida that same night. He never met Roger Wheeler. He didn’t know what Wheeler had done to deserve to die.
He had simply been told by Whitey that the man was a problem. That was enough. But here’s what Blackmass couldn’t put on screen. The Tulsa hit on Roger Wheeler was the killing that cracked the entire Winter Hill operation open. Because Wheeler wasn’t a mobster. He was a businessman, a pillar of the Tulsa community.
The FBI couldn’t bury his death the way they had buried the others. The Oklahoma authorities pushed hard. And as the investigation deepened, the bodies started piling up. John Callahan, the inside man at World High Lie, was found dead in the trunk of his own Cadillac at Miami International Airport on August 2nd, 1982. Johnny killed him. Whitey ordered it.
Callahan knew too much. He was a witness who could connect the Tulsa killing to the gang. Then came Brian Howerin in 1982, a low-level Winter Hill associate who had gone to the FBI to report what he knew about Wheeler. The FBI told Whitey that Howerin was talking. Whitey called Johnny.
On May 11th, 1982, Brian Howerin was machine gunned in his car outside Anony’s Pier 4 restaurant in South Boston. He died in front of a witness named Michael Donahghue, an innocent father of three who had just given Howerin a ride. Donahghue died, too. Collateral damage. Johnny pulled the trigger. By the mid 1980s, Johnny Marterano had killed 20 people.
Some over money, some over disputes, some because Whitey said so. The victims included Edward Connors, a bar owner who had gossiped too much about a previous murder. Thomas King, a Winter Hill rival who Whitey had personally lured to his death and Johnny had buried. Buddy Leonard, killed and dressed in King’s clothing to throw off police.
Richie Castuchi, a rever bookmaker who Whitey had been told was talking to the FBI. The grim irony, Castuchi wasn’t the rat. Whitey was. Whitey had Castuchi killed to deflect suspicion from himself. Johnny did the killing. He didn’t know. The bodies kept stacking. And through it all, Johnny lived under fake names in Florida. Quiet Life, Pool, Sunshine.
He read books. He stayed in shape. He thought he had gotten away clean. January 6th, 1995. The arrest in Boca Raton. The agents found him because of a tax filing mistake. A bank account in his real name that should not have existed. He went to a federal holding facility in Plymouth, Massachusetts.
He was facing race fixing charges from 1979. He thought that was the worst of it. Whitey would take care of his family. Whitey would put money on his books. Whitey would handle it. Whitey was a standup guy. That’s what Johnny believed. Then in late 1995, his attorney came to see him with documents, federal court filings, indictments unsealed.
And in those documents was the truth. Whitey Bulier had been a federal informant since 1975. So had Steven Flemmy for 20 years. While Johnny killed for them, fled for them, did time for them, took the weight for them, they had been sitting in FBI debriefing rooms naming every member of the Winter Hill gang to John Connelly. Every man Johnny had ever trusted.
Every man he had killed for was a rat. The story goes that he was eating a steak in the federal holding cell when his lawyer handed him the papers. He read them. He put the steak down. He didn’t say anything for a long time. Then he looked up and said one sentence. I’m done. Tell them I’ll talk.
That moment somewhere in a federal lockup in late 1995 ended the Whitey Bulier era. Johnny Marterano agreed to cooperate. >> I killed 20 people for Whitey Bulier and then he betrayed me. >> He named every killing, every co-conspirator, every body, every location. He gave the federal government a roadmap to dismantle the Winter Hill gang and the corrupt FBI agents who had protected it.
John Connelly, the FBI agent who had run Whitey for 25 years, was convicted of rakateeering in 2002 and seconddegree murder in 2008. He’s serving 40 years. Steven Fleming plead guilty to 10 murders and is serving life. Whitey Bulier fled before the indictment, lived 16 years as a fugitive, was caught in Santa Monica in 2011, was convicted in 2013, and was beaten to death in his prison cell on October 30th, 2018 by inmates who knew he was a rat. Johnny Marterano.
He got 12 years, 12 years for 20 murders. The plea deal was the most controversial in modern American legal history. The victim’s families called it obscene. The prosecutors called it necessary. Without Marterano, there was no case against Connelly, no case against Bulier, no case against the FBI’s top echelon informant program.
He served his sentence at a federal medium security facility. He was released in 2007. He moved back to the Boston suburbs. He sold real estate. He sold a book to a journalist named Howie Carr. He sat down with Steve Croft on 60 Minutes and explained calmly why he didn’t consider himself a murderer. Because he said he had a code.
He never killed women. He never killed children. He never killed anyone who didn’t, in his estimation, deserve it. The families of Michael Donahghue, the innocent father who happened to be giving Brian Howerin a ride, do not agree. What this story reveals is the price of the bargain. The FBI used Whitey Bulier to take down the Italian Patriarcha family in New England. It worked.
They got their convictions. But the cost was that Whitey Bulier ran the streets of Boston with federal protection for 25 years. And Johnny Marterano killed 20 people while the agents who could have stopped it looked the other way. That’s the real story. Not the glory, not the loyalty, not the code, the bargain. The government decided that one set of crimes was acceptable to solve another.
And 20 families paid the bill. Roger Wheeler’s son still speaks about his father. He has not stopped. He never will. Because somewhere in Massachusetts tonight, Johnny Marano is sitting in a comfortable home watching television. A free man, the executioner. 20 bodies, 12 years served. 7 months per life.
That’s the math the United States government agreed to. And that’s the story Black Mass left out. If you found this story as disturbing as we did, hit subscribe. We drop a new mob documentary every week. Drop a comment below. Was Johnny Martano a vigilante or the biggest mass murderer to ever walk free in American history? Tell us what you think.
