1995, January. A payphone rings inside a modest brick row house on East 3rd Street in South Boston. The man who picks it up is not just anybody. He is the president of the Massachusetts State Senate, the most powerful elected official in the Commonwealth not named governor. The voice on the other end belongs to his older brother.
His older brother is, at that exact moment, the most wanted fugitive in America. 16 days earlier, James Joseph Bulger, the man the world knows as Whitey, walked away from his Quincy apartment with a tip from a corrupt FBI agent and vanished. He would stay vanished for 16 years. And the very first phone call he made from the run, the call to [clears throat] the family he left behind, was answered by his kid brother, William Michael Bulger, Billy, president of the Senate, future president of the University of Massachusetts, the man who
took that call and never told a soul. This wasn’t just another mobster’s relative. Billy Bulger was a 5’6 former classical scholar who quoted Cicero on the Senate floor, who ran Massachusetts politics with an iron grip for 18 years, who hosted an annual St. Patrick’s Day breakfast that every Kennedy, every congressman, and every presidential hopeful in America had to attend if they wanted to win Massachusetts.
He was the most feared political operator in New England. And his older brother was burying bodies in basements 4 miles from the State House. This is the story of how two boys from a South Boston housing project went in opposite directions and stayed loyal to each other anyway. How one became a killer protected by the FBI, and the other became the kingmaker who refused to give him up.
This is the part the Black Mass movie never showed you, the part that’s bigger than the movie because the movie was about the gangster. The real story was about his brother. Here’s what the history books skipped. Whitey Bulger was an FBI informant. Everybody knows that now. What they forget is that while Whitey was running South Boston for the FBI, Billy Bulger was running Massachusetts for himself and nobody.
Nobody in the Bureau, nobody in the press, nobody at the Justice Department, nobody on Beacon Hill wanted to ask the question out loud. What did the brother know? You have to understand where they came from. The Bulger family lived in the Old Harbor project on Logan Way in South Boston.
A red brick public housing development built in the 1930s. James Joseph Sr., the father, lost his left arm in a railroad accident as a young man. He worked when he could. The family was poor. Six kids in a small apartment. The mother, Jean McCarthy Bulger, was the spine of the household. Irish Catholic, daily mass, rosary at night. She believed in education the way she believed in God, total, unquestioning.
There were three boys who mattered. James, born in 1929. William, born in 1934. And John, the youngest, who would grow up to be the clerk magistrate of Boston Juvenile Court. Three brothers, three paths, one last name that would mean trouble in Massachusetts for the next 70 years.
Jimmy was the wild one from the start. Blonde hair so bright the neighborhood started calling him Whitey when he was 8 years old. He hated the name. He’d swing on you if you used it, but it stuck. By 13, he was running with a street gang called the Shamrocks. By 14, he had his first arrest. Larceny, then assault, then armed robbery. He was sent to a juvenile reformatory.
He came out worse. He always came out worse. And here’s a detail that tells you everything about the strangeness of this family. In 1949, when Whitey was 19 years old and already a known street tough, he and his little brother Billy and a few neighborhood kids appeared on a children’s television program called The Howdy Doody Show.
They were in the Peanut Gallery. Whitey Bulger on Howdy Doody. Smiling for the camera. Two years before his first federal prison sentence. Billy was the opposite, quiet, studious. He read everything. While Whitey was kicking down doors, Billy was kneeling at 6:00 a.m. mass before walking to school.
He went to Boston College High, then Boston College, then Boston College Law. Three degrees from the Jesuits. He memorized Virgil in Latin. He could recite the entire Aeneid from memory by the time he was 25. The neighborhood watched these two brothers and shook their heads. The smart one and the savage one. Same kitchen table, same mother’s rosary, different planets.
In 1956, Whitey got hit with a federal indictment for armed bank robbery. He pulled three banks in three states. The FBI caught him in Revere with a girlfriend and a suitcase of cash. He pleaded guilty. 20 years, federal time. He served at Atlanta, then Alcatraz, then Leavenworth. Nine years total. The Alcatraz years would shape him.
He claimed later he was a test subject in the CIA’s MK Ultra program. He said they gave him LSD for 50 weeks and he never slept right again. Some of that is documented, some of it isn’t. What’s is is the man who walked out of Leavenworth in 1965 was harder, colder, and more careful than the kid who went in. While what he was inside, Billy was rising. He passed the bar in 1961.
He ran for state representative in 1960. He won. He was 26 years old. He represented South Boston, the same [clears throat] streets his brother had terrorized. And here’s the thing, the neighborhood loved him for it. In South Boston, a place where loyalty was the only currency that mattered, having a brother in federal prison wasn’t a liability. It was a credential.
It meant you were one of them. Billy never ran from the connection. He embraced it. He used to joke about it. That was the genius of the man. By 1970, Billy was in the state Senate. By 1978, he was president of the state Senate. He would hold that seat for 17 consecutive years. The longest tenure of any Senate president in Massachusetts history.
He controlled the budget. He controlled committee assignments. He controlled which bills lived and which bills died. Governors learned not to cross him. Michael [snorts and clears throat] Dukakis tried. Michael Dukakis lost. Bill Weld tried later. Bill Weld lost, too. Billy ran the building, period. He had a style nobody could replicate.
5’6″, bow tie, a voice that could go from County Cork lilt to courtroom Latin in the same sentence. He’d quote Shakespeare at a budget hearing. He’d quote Cicero at a press conference. He’d quote his mother at a wake. He was funny. He was vicious. He was charming. And underneath all of it, he was a machine politician of the old school.
He remembered every favor. He remembered every slight. He never forgot a name. He never forgot a vote. And then there was the breakfast. Every St. Patrick’s Day, Billy Bulger hosted a political breakfast in South Boston. It started small in the 1970s. By the 1980s, it was the most important political event in New England.
Senators came. Governors came. Presidential candidates came. Tip O’Neill came. Ted Kennedy came. John Kerry came. Bill Clinton came. They had to come. If you skipped Billy’s breakfast, you weren’t serious about Massachusetts. The room was packed. The cameras rolled. And Billy stood at the microphone and did stand-up comedy for an hour.
He sang Irish songs. He roasted the governor sitting 3 ft from him. He told stories about the neighborhood. And every single year, without fail, he made a joke about his brother, the fugitive, the killer, the most wanted man in America. Billy would lean into the microphone and say something like, “I’d like to thank my brother Jim for not being able to make it this morning.
” He sends his regards from somewhere. The room would explode in laughter. Politicians who knew better laughed along. Reporters who should have been asking harder questions laughed along. It was theater. It was deflection. It was a brother turning his brother’s body count into a punchline. And it worked. For decades, it worked.
While Billy was telling jokes at the Park Plaza, Whitey was running South Boston with a machine pistol and an FBI badge in his pocket. He’d come home from Leavenworth in 1965. He went to work for the Killeen gang. Then he switched sides and helped wipe out the Killeens. By the mid-1970s, he was second in command of the Winter Hill gang.
Then he was the boss. He partnered with Stephen Flemmi, a stone-cold killer with his own FBI handler. Together, they built the most profitable Irish criminal enterprise in American history. The schemes were beautiful in their simplicity. Extortion. If you owned a bar in South Boston, you paid Whitey. If you ran a bookmaking operation in Dorchester, you paid Whitey.
If you wanted to move cocaine through the docks, you paid Whitey. The numbers got staggering. By the 1980s, the Bulger organization was clearing over $25 million a year in tribute payments alone, and every dime of it was protected. Because Whitey Bulger was top-echelon informant in the FBI’s files. He had a handler, Special Agent John Connolly, a South Boston kid who grew up two blocks from the Bulgers.
A kid who remembered being protected by Whitey on the playground when he was 8 years old. Connolly fed Whitey everything. Wiretaps, informants, indictments before they came down. In 1981, a businessman named Roger Wheeler bought the Telex Corporation. He found out the Winter Hill gang was skimming millions through World Jai Alai. He hired an investigator.
The investigator was named John Callahan. Whitey found out. On May 27th, 1981, Wheeler was shot in the head in the parking lot of the Southern Hills Country Club in Tulsa, Oklahoma. One bullet between the eyes. Three months later, Callahan was found in the trunk of his Cadillac at Miami International Airport.
Two bullets in the head. The FBI knew Whitey ordered both hits. The FBI did nothing because John Connolly buried the files. It went on for years. Bodies in basements, bodies in marshes, bodies under the Neponset River Bridge. Deborah Hussey, Deborah Davis, Bucky Barrett, Brian Halloran, Michael Donahue, an innocent truck driver who happened to be giving Halloran a ride. All of them killed.
Some buried by Whitey personally with a shovel and a bag of lime. And 4 miles away at the State House, Billy Bulger was approving the state budget and quoting Yates. Now, here’s the question. The question nobody wants to answer cleanly. What did Billy know? He knew his brother was a criminal. That was public knowledge.
The newspapers wrote about it every week. The Boston Globe ran a four-part series on Whitey in 1988 that essentially exposed him as an FBI informant. Billy read the papers. Billy was not stupid. But did Billy know about the murders? Did Billy know about the bodies? Did Billy know about John Connolly? In 1995, the federal indictment came down.
On December 23rd, Whitey got the tip from Connolly. He ran. He took his girlfriend Catherine Greig and a duffel bag of cash and identity documents and he disappeared. He went to Grand Isle, Louisiana. Then to New York. Then eventually, after years, to a stucco apartment on 3rd Street in Santa Monica, California.
And in January of 1995, weeks after he ran, the phone rang at the home of a Bulger family friend named Edward Phillips. Whitey was on the line. Billy was summoned. Billy took the call. According to Billy’s own later sworn testimony, he and Whitey spoke briefly. Whitey said he was okay. Billy told him not to worry about the family.
Billy did not ask where he was. Billy did not tell him to come in. And here is the part that mattered. Billy did not call the FBI. For 8 years, that phone call sat in the shadows. Whitey stayed gone. Bodies kept getting dug up. The FBI scandal got bigger and bigger. John Connolly was indicted in 1999 for racketeering and obstruction.
The story of FBI corruption in Boston became a national scandal. And Billy Bulger by this point had left the Senate. In 1996, he had been appointed president of the University of Massachusetts, the state’s flagship public university system. Five campuses, 60,000 students, a $200,000 salary, the most prestigious academic job in New England.
They handed it to a man with no academic experience because nobody in Massachusetts had the nerve to tell Billy Bulger no. Then came June of 2003. The United States House of Representatives Committee on Government Reform, chaired by Congressman Dan Burton of Indiana, opened hearings on FBI corruption in Boston. They subpoenaed Billy Bulger.
They wanted him under oath. They wanted to know about the phone call. They wanted to know what he knew. On June 19th, 2003, Billy Bulger sat at the witness table in room 2154 of the Rayburn House Office Building in Washington, D.C. Bow tie, wire-rimmed glasses. He was 69 years old. The cameras were rolling. C-SPAN was carrying it live.
And Billy Bulger, the master orator, the man who could quote Cicero from memory, invoked the Fifth Amendment. He refused to answer. He said his appearance had been compelled and he would not testify under those conditions. The hearing was rescheduled. They granted him immunity. He came back. And on June 20th, 2003, he finally talked.
He admitted the 1995 phone call. He admitted he had not contacted law enforcement. He said, “I do have an honest loyalty to my brother, and I care about him. He said, ‘I don’t feel an obligation to help everyone catch him.'” Those words went around the world. The president of the University of Massachusetts had just told the United States Congress that he would not help catch his fugitive brother who was wanted for 19 murders.
The reaction was nuclear. Mitt Romney, the governor of Massachusetts at the time, called for Billy’s resignation. The Boston Globe called for his resignation. The faculty of UMass called for his resignation. Billy resisted. He always resisted. But the math had changed. He no longer ran the Senate.
He no longer controlled the budget. The favors he had banked for 40 years were no longer enough. On August 6th, 2003, William Michael Bulger resigned as president of the University of Massachusetts. He took a $960,000 severance package and went home to South Boston. He never apologized. Not once. In his 2009 memoir, While the Music Lasts, and in every interview he ever gave afterward, he said the same thing.
He loved his brother. He had no information about his brother’s crimes. He had nothing to apologize for. Some people believed him. Most people didn’t. The truth was probably somewhere in between, and nobody was ever going to find it. Eight years after Billy’s resignation on June 22nd, 2011, Whitey Bulger was arrested in Santa Monica, California.
81 years old, white beard. He had been hiding for 16 years in an apartment with 30 firearms and $800,000 in cash stuffed into the walls. He was extradited to Boston. He went to trial in 2013. The jury convicted him on 31 counts of racketeering, extortion, and money laundering. They found him responsible for 11 of the 19 murders charged.
He got two life sentences plus 5 years. He was sent to a federal penitentiary in Hazelton, West Virginia. On October 30th, 2018, within 12 hours of his arrival, two inmates beat him to death with a sock filled with a padlock. He was 89 years old. He died on the floor of his cell. Billy did not attend the funeral mass publicly.
Billy is still alive as of this telling. He lives quietly. He reads. He tends to his family. He occasionally surfaces at a wake or a christening in South Boston. And the old neighborhood still treats him with the deference of a king because that’s what he was. For 40 years, William Michael Bulger ran Massachusetts. And nobody, not the FBI, not the Globe, not the governor, not the United States Congress, ever made him answer the one question that mattered.
Did you protect him? Did you know? He took the answer with him into retirement. He may take it to his grave. Here is what this story really reveals. The Departed showed you the cop and the killer. Hollywood loves that symmetry. But the deeper Boston story was never about the cop. It was about the brother. It was about how a city the size of a major American media market allowed two boys from a housing project to run both halves of the same machine for 30 years.
The criminal machine and the political machine. Same blood. Same kitchen table. Same mother’s rosary. And not one institution in Massachusetts, not the press, not the FBI, not the state police, not the courts, had the nerve to ask the obvious question until it was too late. That’s the real lesson of the Bulgers.
Power doesn’t always wear a gun. Sometimes power wears a bow tie. Sometimes power quotes Virgil. Sometimes power tells a joke about its fugitive brother and the whole room laughs. And while the room is laughing, the bodies are being buried 4 miles away. The brother who buried them died on a prison floor in West Virginia.
The brother who never told is still here. Still quiet. Still loyal. Still the most fascinating political figure Massachusetts ever produced. Because in the end, the most dangerous Bulger was never the one with the machine pistol. It was the one with the gavel.
