The Whitey Bulger trial ended on August 12, 2013, when a Boston federal jury convicted the former Winter Hill Gang leader on 31 of 32 racketeering-related counts, finding him responsible for 11 of the 19 murders charged in the indictment.1U.S. Department of Justice. Federal Jury Convicts James “Whitey” Bulger Three months later, U.S. District Judge Denise J. Casper sentenced him to two consecutive life terms plus five years. The case exposed a nearly three-decade corrupt relationship between Bulger and the FBI agents who were supposed to be investigating him.
What Bulger Was Charged With
The indictment described Bulger as the leader of a Boston criminal organization from 1972 to 1999. The central charge was a violation of the Racketeer Influenced and Corrupt Organizations Act, which makes it a federal crime to run an enterprise through a pattern of criminal activity.2Office of the Law Revision Counsel. 18 USC 1962 – Prohibited Activities Prosecutors used RICO to bundle dozens of separate crimes into a single case with Bulger at the top of the pyramid.
Nineteen murders were alleged as predicate acts of the racketeering conspiracy.3Justia. In re Bulger Beyond the killings, the government charged Bulger with extorting bookmakers, drug dealers, and legitimate business owners under threat of violence, along with money laundering, weapons possession, and conspiracy to traffic narcotics.
The Immunity Defense the Judge Rejected
Before trial, Bulger’s lawyers announced an unusual theory: that Jeremiah O’Sullivan, a now-deceased federal prosecutor who had led the New England Organized Crime Task Force, had given Bulger blanket immunity from prosecution in exchange for his work as an informant. If a jury believed it, the government would effectively have licensed his criminal activity for decades.
Judge Casper ruled that any alleged immunity agreement was a legal question for the court, not a factual defense for the jury.3Justia. In re Bulger An earlier judge assigned to the case had gone further, concluding that even if O’Sullivan had made such a promise, he lacked the authority to immunize the crimes at issue.
Bulger refused to argue the immunity issue to the judge, insisting the question belonged with the jury. The First Circuit Court of Appeals called that a “calculated risk” resting on a “misguided” belief and upheld the trial court. With the immunity theory gone, Bulger had no coherent defense left to present. He chose not to testify.
The Witnesses Who Sank Him
The prosecution built its case on three former members of Bulger’s inner circle, each of whom had cut cooperation deals to avoid harsher punishment.
John Martorano
Martorano, a Winter Hill Gang hitman, described Bulger as a hands-on killer who often drove during hits. He walked jurors through a series of murders in which the wrong people were sometimes shot before the intended targets were killed. Martorano served roughly 12 years in exchange for his testimony.
Stephen Flemmi
Flemmi, Bulger’s closest partner, gave the trial’s most disturbing testimony. He said he watched Bulger strangle Deborah Hussey, Flemmi’s own stepdaughter, at the top of a basement staircase. He also described the killings of Arthur “Bucky” Barrett and John McIntyre in what prosecutors called a “death house,” where gang members pulled the victims’ teeth to defeat identification and buried the bodies in the basement. Flemmi testified that Bulger insisted on killing anyone he thought might inform. Flemmi admitted to 10 murders and avoided the death penalty through his deal.
Kevin Weeks
Weeks, a longtime Bulger lieutenant, corroborated key pieces of the other two accounts and described how the extortion network operated day to day. He also confirmed the corrupt relationship between Bulger and his FBI handlers.
Defense counsel hammered all three as career criminals who had bought lighter sentences by telling prosecutors what they wanted to hear. The volume of overlapping detail across three witnesses made that argument hard to land.
The FBI Corruption Exposed at Trial
What set the Bulger case apart from an ordinary mob prosecution was the FBI’s role in enabling him. In 1975, agent John Connolly recruited Bulger as a “top echelon informant” who would feed intelligence on the rival Italian-American Mafia in exchange for protection. The arrangement lasted nearly three decades.
Connolly and his supervisor, John Morris, accepted cash payments from Bulger and Flemmi totaling at least $235,000. In late 1994, Connolly tipped Bulger off to a pending indictment, and Bulger and his girlfriend Catherine Greig disappeared before agents could arrest them. He spent 16 years as a fugitive and was captured in Santa Monica in June 2011.4FBI. Most Wanted Fugitive Bulger Captured in Santa Monica
Connolly was convicted of federal racketeering charges in 2002 and sentenced to 10 years. While serving that term, he was indicted in Florida for second-degree murder in the 1982 killing of businessman John Callahan, a potential witness against Bulger’s crew. A Florida jury convicted him, and a judge added 40 years to run after the federal sentence.
The Verdict
The jury deliberated more than 32 hours across five days before returning verdicts on August 12, 2013. It convicted Bulger on 31 of the 32 counts and held him responsible for 11 of the 19 alleged murders.1U.S. Department of Justice. Federal Jury Convicts James “Whitey” Bulger Jurors could not reach unanimous decisions on six of the murder allegations and found the evidence insufficient on the others. One juror later described the deliberations as “insane” and “heated” and said he personally believed the evidence supported guilty findings on all 19 murders.
The racketeering conspiracy conviction was the linchpin. The jury agreed that Bulger had run the Winter Hill Gang as a criminal enterprise for roughly 27 years, and the extortion, money laundering, and drug convictions followed from that finding.
The Sentence
In November 2013, Judge Casper sentenced Bulger, then 84, to two consecutive life terms plus five years. She told him the “scope, callousness and depravity” of his crimes were “almost unfathomable.” The court ordered him to forfeit $25.2 million and pay $19.5 million in restitution to the victims’ families.1U.S. Department of Justice. Federal Jury Convicts James “Whitey” Bulger The sentencing hearing gave the families their first chance to speak to Bulger directly in court.
What Happened After
Bulger did not die of old age. On October 30, 2018, less than 12 hours after being transferred to U.S. Penitentiary Hazelton in West Virginia, he was beaten to death in his cell. He was 89 and using a wheelchair. Federal prosecutors later charged three inmates, Fotios “Freddy” Geas, Paul DeCologero, and Sean McKinnon, in connection with the killing. Prosecutors alleged Geas and DeCologero entered the cell shortly after doors opened at 6 a.m. and struck Bulger in the head repeatedly with a lock wrapped in a sock, while McKinnon acted as a lookout. Geas and DeCologero were charged with conspiracy to commit first-degree murder and aiding and abetting first-degree murder; McKinnon was charged with conspiracy and making false statements to a federal agent.