In 2006, Martin Scorsese released The Departed and finally won an Oscar. Matt Damon played Blaze, a mole inside the Massachusetts State Police. He feeds information to Jack Nicholson’s crime boss. He gets caught. He gets shot in an elevator. Credits roll. Um >> >> except the real story did not end that way.
The real FBI agent who inspired that character was John Connolly. He was responsible for the murders of at least three men whose names he personally handed to the mob. And as of this recording, he is alive, out of prison, and collecting his federal pension. Southie, 1949. An 8-year-old kid named John Connolly is walking through the old Harbor housing project when older boys corner him over an argument about a ball.
He is outnumbered and about to get beaten. Then a 19-year-old from a few doors down chases the bullies off and buys the kid an ice cream cone. That 19-year-old was Whitey Bulger. Connolly never forgot it. He grew up in the same brick housing project as the Bulgers and looked up to Whitey the way younger kids look up to the toughest guy on the block.
He stayed close to Whitey’s younger brother Billy, who would later become president of the Massachusetts State Senate. Billy encouraged him to go to college. He did. He went to Boston College, then law school. In October 1968, he joined the FBI after a recommendation from House Speaker John McCormack. He served in Baltimore, San Francisco, and New York.
Then in 1973, he got what he had been waiting for, a transfer home. Back to Boston. The timing was perfect. The FBI had been trying to dismantle the Italian Mafia in New England for years. They needed inside information. Connolly told his bosses he could deliver something nobody else could, a high-level informant from inside the Irish mob.
Connolly made his move in 1975. He went to Whitey Bulger, the same man who had chased off those bullies 25 years earlier, and recruited him as a top-echelon FBI informant. On paper, the mission was simple. Bulger would help the FBI destroy the the Patriarca crime family. In exchange, the FBI would look the other way on his own operations.
Connolly would manage the relationship. And at first, it worked exactly as planned. Bulger and his partner, Stephen Flemmi, gave the FBI the layouts of Mafia meeting spots. They literally drew diagrams so agents could plant listening devices. In 1981, those bugs were installed at the Prince Street headquarters of Gennaro Angiulo, the boss of the Boston Mafia’s North End operation.
A 3-month wiretap operation captured Angiulo incriminating himself in racketeering and murder. On September 19th, 1983, Angiulo was arrested. He was convicted in 1986. The Italian mob in Boston was finished. Uh the FBI celebrated. Uh Connolly received eight commendations over his career from every director from J.
Edgar Hoover through William Sessions. He was their star agent. He was the architect of the most successful organized crime operation in New England history. But Bulger had not become an informant to help the government. He had become an informant to eliminate his competition. And once the Italians were gone, he filled the power vacuum himself.
Connolly was not managing an asset. He was protecting a business partner. And that partnership was about to cost people their lives. I think this is the part of the story most documentaries skip past. The FBI did not dismantle the Italian mob through good police work. They handed New England to one criminal organization um in exchange for taking out the other one >> >> and called it a victory.
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Here is what the FBI’s star agent was actually doing while those commendations hung on his wall. In May 1981, a businessman named Roger Wheeler owned a company called World Jai Alai. Wheeler discovered that someone inside his organization was skimming money for the Winter Hill gang, approximately $10,000 a week.
He started asking questions. >> >> He wanted an investigation. On May 27th, 1981, a hitman named John Martorano shot Wheeler in the head as he sat in his car after playing golf at Southern Hills Country Club in Tulsa, Oklahoma. The murder happened 1,500 miles from Boston, but the order came from Whitey Bulger.
The Wheeler killing created a problem. Too many people knew too much. And one of them was about to talk. A Winter Hill gang associate named Brian Halloran walked into the FBI in January 1982 and offered to cooperate. Halloran had witnessed Bulger and Flemmi planning the Wheeler murder. Uh he knew they had asked him to be the shooter, and when he refused, they had Wheeler killed anyway.
Uh Halloran was willing to testify. Uh Connolly learned about it. He was supposed to be running informants, not protecting them. But he told Bulger. Halloran was sitting in a waterfront bar in Boston. It was May 11th, 1982. A truck driver named Michael Donahue offered to give him a ride home. Donahue was 32 years old.
He had no connection to organized crime. He was just doing a favor for an acquaintance. Um they never made it. Um Bulger’s crew opened fire on the car as it left the bar. Halloran and Donahue um were both killed. The innocent truck driver died because he was in the wrong place at the wrong time. And the FBI informant died because Connolly handed his name to the mob.
But the chain of deaths was not finished. The Wheeler murder still had loose ends. That summer, the FBI started looking at a former World Jai Alai executive named John Callahan. Callahan had been the company’s president before Wheeler bought it. He had introduced Bulger to the company in the first place. Investigators believed Callahan would crack under questioning and implicate everyone.
Connolly warned Bulger. He indicated that Callahan would not hold up. Hitman John Martorano lured Callahan to Miami on July 31st, 1982. He shot him, stuffed his body in the trunk of a Cadillac, and left the car in a parking lot at Miami International Airport. Three days later, police checked the trunk and found Callahan’s bullet-ridden corpse. He was 45 years old.
Connolly did not pull a trigger. He did something worse. He handed over the names of people who had trusted the FBI with their lives. And those people died because of it. I would argue Connolly belongs in a worse moral category >> >> than the men who pulled the triggers. Martorano was a hitman. He never pretended to be anything else.
Connolly wore the badge, took the oath, and used that position to kill three witnesses by phone. Two years later, he did it again. Uh fisherman named John McIntyre from Quincy, Massachusetts, got arrested for drunk driving in 1984. Normally, that would be the end of it, but McIntyre had a secret.
He had been part of a failed attempt to run guns to the IRA aboard a boat called the Valhalla. During his arrest, he started talking about it. Authorities learned details of the gun-running operation. The crew had worked with Bulger. Connolly learned McIntyre was cooperating. He told Bulger.
Bulger lured McIntyre to a house in South Boston. On November 30th, 1984, Bulger interrogated him and murdered him personally. >> >> McIntyre was 32 years old. A drunk driving stop had become a death sentence. Three informants, three murders, one FBI agent connecting them all. And somehow, nobody inside the Bureau noticed. Actually, somebody did notice.
John Morris, Connolly’s supervisor on the organized crime squad, knew exactly what was happening. He knew because he was on the payroll, too. Bulger’s gang paid Morris $7,000 in cash bribes. They sent him so many bottles of expensive wine uh that they nicknamed him Vino. Uh they paid for airline tickets for his mistress, who happened to be his secretary.
They gave him a silver-plated wine bucket. And in 1979, Morris personally persuaded federal prosecutor Jeremiah O’Sullivan to drop racketeering charges against Bulger and Flemmi. There were not one, but two corrupt FBI agents running the Boston organized crime operation. And one of them was the boss. The money Connolly received was staggering.
During the 1980s, he earned between $45,000 and $65,000 a year as an FBI agent. In that same period, he bought a 27-foot Sea Ray boat for $46,000, a South Boston condo for 63,000, a second condo in Brewster for 80,000, and land in Chatham for 98,000. Then he built a house on the land for 132,000. An IRS special agent named Sandra Lemansky calculated the math at trial.
It did not add up. Stephen Flemmi later testified that he and Bulger paid Connolly $235,000 in all over the years. He said they gave him envelopes with $5,000 for for vacations and $10,000 at Christmas. In 1983 alone, Connolly received two separate receiving the second one, he looked at Flemmi and said, “I am one of the gang.
” Flemmi also testified that they paid cash bribes to five other FBI agents in Boston. The corruption ran deeper than anyone outside the organization knew. If you are finding the real version of this story more disturbing than anything Hollywood showed you, subscribe. New episodes drop every week. For a while it seemed like nobody >> >> would ever expose any of this.
Connolly retired from the FBI in 1990. Before leaving, he filed a memo stating that Bulger and Flemmi had retired from organized crime and gone into legitimate business. That was a lie. Uh but it went into the official record. Morris, however, was getting nervous. In 1988, 2 years before Connolly retired, Morris became terrified that someone was about to expose the whole arrangement.
So he did something calculated. He leaked information about the FBI’s protection of Bulger to the Boston Globe in an off-the-record interview. He did not do it out of conscience. He did it to get ahead of a story he knew was coming to control the narrative before it controlled him. The Globe ran a report. And slowly, the dominoes started falling.
On December 23rd, 1994, Connolly learned that a RICO indictment against Bulger was imminent. He had been retired for 4 years. He had no official access to that information. He still found out. And he called Bulger. Bulger grabbed approximately $800,000 in cash and fled Boston with his girlfriend, Catherine Greig. For the next 16 years, America’s most wanted gangster lived in a rent-controlled Santa Monica apartment under the name Charlie Gasco.
He paid $1,145 a month in cash, bought identities from homeless people, and walked his two cats. He stayed completely off the radar. When Bulger was finally captured, investigators found $800,000 hidden in the walls of his apartment, the same amount he had taken when he fled.
Connolly was indicted on December 22nd, 1999 on federal charges of alerting Bulger and Flemmi to investigations, falsifying FBI reports, and accepting bribes. Flemmi, Martorano, and Kevin Weeks all testified against him. Morris testified, too, having received full immunity for his cooperation. In 2002, Connolly was convicted of racketeering and obstruction of justice.
He was sentenced to 10 years in federal prison. Uh but that was the federal case. The state case was still coming. In 2008, Florida prosecutors charged Connolly with second-degree murder for the Callahan killing. The legal theory was unusual. Uh Connolly was demonstrably on Cape Cod when the trigger was pulled in Miami, but prosecutors argued that he was a principal in the first degree because he provided the information that caused the murder to happen. The tip-off was the trigger.
The jury agreed. On November 6th, 2008, Connolly was convicted. In January 2009, uh Judge Stanford Blake sentenced him to 40 years in Florida state prison, um to run consecutively after his federal sentence. At the sentencing, the judge looked at him and said that he had crossed over to the dark side.
He had left law enforcement. He had forfeited that badge that so many people wear proudly. The conviction did not go unchallenged. A Florida appellate panel initially overturned it in May 2014, voting two to one, finding that Connolly did not carry or discharge the gun. On July 29, 2015, the full court reinstated the verdict, six to four.
One judge wrote that it no longer matters whether Connolly hired a hitman, turned to his mob friends, served as a lookout, provided the gun, or pulled the trigger himself. The information was enough. Meanwhile, Bulger was finally caught. Agents arrested Bulger and Catherine Greig outside their Santa Monica apartment on June 22nd, 2011, acting on tips prompted by an FBI advertising campaign.
He was 81 years old and had been a fugitive >> >> for 16 years. A former model named Anna Bjornsdottir, who had been Miss Iceland in 1974 and lived in the same neighborhood, recognized him from the campaign and called the FBI. Bulger was convicted in August 2013 on 31 of 32 counts, including involvement in 11 murders.
He received two life sentences plus 5 years. But even his story was not over. On October 29th, 2018, at age 89, Bulger was transferred to USP Hazelton, a federal penitentiary in West Virginia known internally as Misery Mountain. 5 hours before he arrived, an inmate named Paul Calogero told his mother in a recorded phone call that the notorious gangster was on his way.
More than 100 uh Bureau of Prisons staff uh knew about the transfer. Nobody protected him. Within hours of arriving, Bulger was beaten to death by multiple inmates. The weapon was a sock wrapped around a padlock. He was 89 years old. A Justice Department Inspector General investigation later found that the killing resulted from multiple layers of management failures, widespread incompetence, and flawed policies.
There was no malicious intent on the part of staff, just bureaucratic blunders that left America’s most notorious informant at the mercy of rival gangsters on his first day at a new prison. And Connolly? In February 2021, he was granted compassionate release from Florida state prison. Prison doctors said he was terminally ill with melanoma and diabetes and likely to die within the year.
He returned to Lynnfield, Massachusetts. >> >> He underwent a 10-hour surgery that resulted in the removal of his ear. He has now outlived that terminal prediction by several years. And here is the detail that makes this story different from the movie. Under federal law, an FBI agent only loses their pension if convicted of espionage or treason.
Murder does not qualify. John Connolly, convicted of second-degree murder for his role in the death of John Callahan, still collects his federal retirement check every month. That one statute tells you more about how the FBI views its own conduct than any internal review ever has. Selling secrets to a foreign government is unforgivable.
Selling informants to a domestic killer is a paperwork issue. >> >> The movie ends with Matt Damon dead in an elevator. The real story continues. In March 2026, Connolly’s lawyers filed a motion in Miami-Dade Circuit Court to vacate his murder conviction. They cited handwritten manuscripts found after Bulger’s death in which Bulger identified supervisor John Morris, not Connolly, as the source who warned him about Callahan.
Bulger called Connolly a sacrificial lamb and said he had deliberately let Connolly take the blame to protect Morris. Morris, of course, received full immunity years ago. He can’t He cannot be prosecuted regardless of of what Bulger’s papers say. If the motion succeeds, the man who spent his career protecting one of the most dangerous criminals in American history could walk away without a single conviction standing.
The FBI agent who fed informants to the mob, who watched three men die because of information he passed, who warned a fugitive to run and let him escape for 16 years, he would be free, cleared, still collecting his pension. The Departed won Best Picture at the 79th Academy Awards.
Martin Scorsese got his Oscar. He later said that nothing in the film was exaggerated. If you want to see another case where the real story behind a famous mob movie turned out to be worse than the film, that video is on screen now.
