Johnny Martorano: The Hitman Whitey Bulger Used to Kill for the FBI

Añadido: 2026-06-07

[00:00:00]May 27th, 1981. 4:12 in the afternoon.

[00:00:04]Southern Hills Country Club, Tulsa, Oklahoma. The parking lot is quiet.

[00:00:09]Midweek. The kind of dry Oklahoma heat that makes the asphalt shimmer. A man named Roger Wheeler has just come off the 18th hole. He's a self-made millionaire, church-going man, father of four. He's wearing golf shoes, carrying his keys, heading toward his Cadillac in the afternoon sun. He never saw the man walking toward him. One shot. Close range. Roger Wheeler was dead before he hit the seat. The shooter walked back to a rental car without breaking stride and was airborne to Florida before sunset.

[00:00:39]His name was Johnny Martorano, and at that point he had already killed at least 15 men for the Winter Hill gang in Boston. Roger Wheeler wasn't a mobster.

[00:00:49]He wasn't a rival. He was a businessman who'd made the mistake of buying a company that the wrong people had been stealing from, and that was enough. This is the story of how a half-Italian, half-Irish kid from the Boston suburbs became the most dangerous hitman the Irish mob ever produced. How the FBI turned a blind eye to his crimes for two decades, and how a single piece of paper in a federal lockup cell in 1995 brought the whole rotten structure crashing to the ground. Boston, 1940. The North End bled into Somerville, and Somerville bled into everywhere else. Johnny Martorano was born December 13th, 1940, into a city that ran on ethnicity. If your name ended in a vowel, you belonged to the Patriarca family's orbit up in the North End. If you were Irish, you ran with the Somerville crews, the Charlestown boys, the South Boston crowd. You didn't mix. You definitely didn't work together, and you were, without question, one or the other.

[00:01:55]Johnny was neither. His father, Angelo, was Sicilian. His mother was Irish. Two bloodlines that shared exactly one thing in common in Boston at that time, a deep mutual suspicion of each other. From the time he was old enough to understand the streets, Johnny existed in a gap between two worlds. Neither side fully claimed him. So, he did what marginalized kids often do. He became somebody nobody wanted to mess with. By his teens, he was already the biggest, most intimidating presence in any room he walked into. Not loud about it, not flashy, just quietly, unmistakably dangerous. By his early 20s, he was working the door at a club called Basin Street South in the South End, running numbers on the side, collecting debts for a loan shark, and learning quickly that violence was the only currency that consistently held its value. It was at Basin Street around 1964 that Johnny met two men who would define his entire life. The first was Howie Winter, a compact, soft-spoken operator from Somerville who ran the Winter Hill section of town and was already consolidating power over every Irish racket north of the city. The second was a wiry, platinum blonde kid from the South Boston housing projects who went by the nickname Whitey, James Whitey Bulger. When Howie Winter looked at this mixed heritage kid from Milton and said he could ride with the crew regardless of his last name, that was a rarer offer in 1964 Boston than it sounds. Johnny took it. And from that point forward, he was Irish in every way that mattered on those streets. The late 1960s Boston was a war zone. The McLaughlin brothers out of Charlestown and the McLean faction in Somerville had been systematically wiping each other out over a dispute that started at a Labor Day cookout in 1961.

[00:03:53]By the time it was over, more than 60 men were dead. The bloodiest gang war in American history since prohibition.

[00:04:00]Martorano fought on the Winter Hill side because Howie Winter had treated him like family. Simple as that. He didn't need ideology. He needed belonging. By 1972, the war was over. Howie had won.

[00:04:14]The Winter Hill gang now controlled bookmaking, loan sharking, truck hijacking, and an elaborate horse race fixing scheme that was generating hundreds of thousands of dollars a week across tracks in six states. The scheme worked through a fixer named Anthony "Fat Tony" Ciulla, who identified jockeys carrying debt and paid them to dictate race outcomes. The gang knew which horses would lose before the gates opened. They bet accordingly. It was almost elegant. Then Ciulla got arrested in 1977.

[00:04:48]He flipped and in 1979, federal indictments landed on 21 members of the Winter Hill operation. Two names were not on the indictment, Whitey Bulger and Stephen "The Rifleman" Flemmi. The reason those two names were missing wasn't insufficient evidence. It was that FBI agent John Connolly, a Southie native who had grown up in the same housing projects as Bulger, had been running Whitey as a top echelon confidential informant since 1975.

[00:05:18]Flemmi, too. For four years, these two men had been sitting in FBI debriefing rooms feeding information on everyone around them. Howie Winter didn't know.

[00:05:27]Johnny didn't know. The men who had bled through the gang wars together had no idea the two people at the top of the organization were federal assets. Howie went to prison. Johnny went on the run, disappearing into Florida under a series of false identities. And before he left, he handed the entire Winter Hill operation to the two men he trusted most in the world. He gave Bulger and Flemy everything, the territories, the customers, the connections, the contacts. He told them to hold it together until he could come back. He trusted them completely. That was the last truly loyal thing Johnny Martorano ever did, and it would destroy him.

[00:06:08]Florida, 1981, the call came in. Roger Wheeler, the new owner of World Jai Alai, a gambling company that Bulger and Flemy had been quietly looting through their inside man, a Boston College accountant named John Callahan, had figured out money was missing. He'd hired auditors. He'd terminated Callahan, and he was clearly prepared to follow the trail wherever it led. Bulger called Martorano. Wheeler needed to be handled. Martorano flew to Tulsa. He'd never met Roger Wheeler in his life. He didn't ask why the man deserved to die. Whitey had said it needed doing. That was enough. The Wheeler murder set off a chain reaction that couldn't be contained. Oklahoma authorities didn't treat a prominent businessman's murder the way Boston handled the deaths of criminals, quietly and incompletely. The investigation pressed hard, and as it closed in, the body count climbed. Callahan was found in the trunk of a Cadillac at Miami International Airport in August 1982.

[00:07:14]Martorano had killed him on Bulger's orders because Callahan was a live wire who knew everything. Then, Brian Halloran, a low-level Winter Hill associate who had approached the FBI about what he knew, was machine-gunned outside Anthony's Pier 4 restaurant in South Boston in May 1982. John Connolly had reportedly tipped Bulger that Halloran was talking. An innocent man named Michael Donahue, who had simply offered Halloran a ride home, died in the same burst of gunfire. He had three kids. He had nothing to do with any of it. By the time Martorano was arrested in Boca Raton on January 6th, 1995, found by federal agents due to a bank account filed under his real name, a careless mistake after 16 years underground, he had killed 20 people.

[00:08:05]The federal holding facility in Plymouth, Massachusetts, late 1995. His lawyer came to see him with documents, federal filings, unsealed indictments, and buried inside them the truth that had been kept from him for 20 years.

[00:08:21]Whitey Bulger had been FBI informant number BS-1444 since 1975. Stephen Flemmi had been feeding the bureau information for just as long. Every man Johnny had killed for, every risk he had absorbed, every year he had spent in hiding, all of it had been done on behalf of two men who were simultaneously informing on the operation to the federal government. The men he'd gone to the mattresses for were rats. The men whose word he'd treated as law had been sitting across from FBI handlers the entire time, trading names and details to stay free while Johnny did the wet work. He put down the paperwork. He sat in silence for a long moment. Then he told his lawyer, "Tell them I'll talk." What followed was the most controversial plea deal in the modern history of American organized crime. Johnny Martorano gave the government everything, every murder, every name, every location, a complete road map. John Connolly, the FBI agent who had run Bulger and Flemmi for decades, was convicted of racketeering in 2002 and second-degree murder in 2008.

[00:09:31]He's serving 40 years. Stephen Flemmi pleaded guilty to 10 murders and is serving life. Whitey Bulger fled Boston, lived as a fugitive for 16 years, was caught in Santa Monica in 2011, convicted in 2013, and was beaten to death in his cell at a federal penitentiary in West Virginia on October 30th, 2018 by inmates who knew exactly what he was. Johnny Martorano received 12 years. 12 years for 20 deaths. He was released in 2007. He moved back to the Boston suburbs. He wrote a book with journalist Howie Carr.

[00:10:11]He sat down for a 60 Minutes interview and explained, without visible remorse, why he didn't consider himself a murderer. Because, he said, he had a code. He never harmed women or children.

[00:10:24]Every man he killed had, in his view, done something to earn it.

[00:10:28][clears throat] Michael Donahue's family, the three kids who lost their father because he offered the wrong man a ride, never got a way in on Johnny's code. This is what Boston's gang era actually cost. Not the mythology, not the code and the loyalty and the leather jackets. The real cost was this. The FBI decided the Winter Hill gang's violence was an acceptable price to pay for dismantling the Patriarca family. They got their Italian mob convictions, and in exchange, Whitey Bulger ran the streets of Boston with federal protection for a quarter century, while Johnny Martorano killed 20 people with no one stopping him. 20 families paid that bill. Roger Wheeler's son has spent decades making sure nobody forgets his father's name. Somewhere tonight in Massachusetts, Johnny Martorano is a free man. The math works out to roughly 7 months of prison time per life taken.

[00:11:25]That's the deal the United States government agreed to. That's the story they couldn't fit into Black Mass.