John Martorano was one of the leaders of the Winter Hill Gang, the Boston-area criminal organization that James Bulger and Stephen Flemmi later came to dominate. Over two decades, by his own account, he killed 20 people. He was a fugitive for 16 years, and when he was finally brought back to face federal charges he made a choice that reshaped one of the largest organized-crime prosecutions in Massachusetts: in September 1999 he agreed to plead guilty and to testify against Bulger, Flemmi and the law enforcement officers who had protected them.
His convictions rest entirely on guilty pleas. In US District Court in Boston he pleaded guilty to a Superseding Information charging ten previously unsolved murders in Massachusetts between 1973 and 1976, with other federal crimes. In 2001 he pleaded guilty in Florida to the second-degree murder of John Callahan, who died in 1982, and in Tulsa to the second-degree murder of Roger Wheeler, who died in 1981. His plea agreement also required him to detail eight further unsolved Massachusetts murders. Eight more killings, in the 1960s, he admitted but was never charged with. He received 14 years in federal prison, with concurrent 15-year terms from Oklahoma and Florida, and walked free in 2007 after about 12 years in custody. His testimony helped convict Flemmi, a former FBI agent and a former State Police lieutenant, and in 2013 he was a central witness at the trial of Bulger himself.
Martorano was born about 1940 or 1941; he was 72 when he testified at Bulger's trial in June 2013. He was raised a Catholic and served as an altar boy, and at that trial he traced his ideas of right and wrong to his upbringing. "My father always taught me that," he told the jury, adding that "the priests and the nuns I grew up with taught me that."
By the 1970s he held a senior place in the Winter Hill Gang. A federal indictment in the later racketeering case described him as one of the group's leaders in that decade, working in a supervisory role under Howard Winter. A First Circuit opinion described John Martorano as potentially the head of the enterprise's enforcement division, a role it summed up as "executing individuals who could prove to be a liability."
His bond with Bulger and Flemmi went beyond business. "They were my partners in crime, they were my best friends, they were my children's godfathers," he said in June 2013.
Martorano admitted 20 killings in all. Eight of them, by his account, took place in the 1960s. They were never charged.
Twelve of the 20, a federal appeals court said, dated from his years with Winter Hill. The federal Superseding Information to which he later pleaded guilty charged ten murders in Massachusetts between 1973 and 1976. In his 2013 testimony he spoke of a conflict with a rival group in 1973 and said that he and others killed the wrong man more than once in that period. He summed up one such death in two words: "Wrong guy."
The other two, Roger Wheeler and John Callahan, died outside Massachusetts, and they are the two killings for which state courts later convicted him.
Martorano never claimed to have acted for pay. He told the Bulger jury that he never killed for money and that he had "always tried to be a nice guy." Prosecutors, however, said that he had acted on the orders of Bulger and Flemmi when Wheeler died, and the federal appeals court that later reviewed the Connolly case set out the reasons the gang wanted Callahan dead. Martorano described himself in other terms. "I didn't enjoy killing anybody. I enjoyed helping a friend if I could," he testified in 2013. On another day of cross-examination he said: "I would rather be considered a vigilante than a serial killer."
Roger Wheeler was 55 years old in the spring of 1981. He had been born in Reading, Massachusetts, north of Boston, and he was the father of five children. By 1981 he lived in Tulsa, Oklahoma.
He died in Tulsa on May 27, 1981. For almost two decades no one was charged. When Martorano entered his plea agreement in 1999, the Wheeler case was among the killings he admitted. A federal judge in Boston recorded in 2001 that the investigations of the Wheeler and Callahan murders had been impeded by some members of the FBI "in an effort to protect Bulger and Flemmi."
The First Circuit, reviewing the case of the former FBI agent John Connolly, set out evidence that Martorano gave on that point. He testified that Connolly told Bulger and others that Brian Halloran, a gang associate, had implicated Martorano in the Wheeler murder.
John B. Callahan was a Boston man who had known Martorano for decades. Martorano called him a close friend. Callahan died in Florida on August 1, 1982, the second of the two killings outside Massachusetts that Martorano later admitted in court.
The federal appeals court that reviewed Connolly's conviction described the background. As investigators in Boston pressed their inquiry into the Wheeler case, Connolly warned the group that they would "all go to jail" if something did not happen to Callahan. Martorano and an associate then killed Callahan, the court said, to deflect the Boston investigation. Martorano told the Bulger jury that Bulger "insisted on it."
Under cross-examination in 2013, defense lawyer Hank Brennan put it to him directly: "You even lied to your best friend, John Callahan, before you murdered him." Martorano replied: "To me that was a necessity."
Martorano's first federal case came in 1979, when he was indicted on racketeering charges with Howard Winter. He did not stand trial. He became a fugitive and stayed one from 1979 until January 1995, when he was picked up in Florida. The Wheeler and Callahan cases both fell within those years of flight.
In August 1995 a federal grand jury in Boston indicted him again, this time on racketeering and related charges tied to gambling, loan sharking and extortion. The charges were first brought in the case that named Flemmi, and they were later alleged in a separate indictment. Salemme, Bulger, Flemmi and others were defendants in the wider prosecution, which ran through several superseding indictments.
The case turned into a long inquiry into the FBI's handling of its informants. The defense argued that the bureau had given Flemmi and Bulger free rein to commit crimes short of murder. US District Judge Mark L. Wolf, who presided, issued a series of decisions in 1999 in the matters of Salemme, Flemmi and Martorano.
For Martorano, the most important fact to emerge from those years was that his two partners had been informants for the FBI. He later said he learned it in 1995 and called it the "worst day of my life"; other evidence places the disclosure in a judge's ruling in 1997. "After I heard that they were informants, it sort of broke my heart," he told the Bulger jury. His view of informers was plain. "An informant is a Judas, a rat, a no-good guy," he said in 2013.
Martorano began plea negotiations with federal prosecutors in 1998. By September 1999 the terms were settled. On September 9, 1999, he agreed to plead guilty to federal racketeering charges and to testify against Bulger and Flemmi, a deal that could free him in less than eight years. He was 58, and he had admitted killing 20 people, Roger Wheeler among them.
On September 30, 1999, he pleaded guilty in US District Court in Boston to the Superseding Information. It charged him with ten previously unsolved murders committed in Massachusetts between 1973 and 1976. The plea agreement covered eight more unsolved Massachusetts murders, which he agreed to detail, and the murders in Oklahoma and Florida. The First Circuit later summed up the arrangement: "He pled guilty to ten (federally charged) murders, some other federal crimes, and two state murder charges." In return he was required to cooperate against Bulger, Flemmi and corrupt members of law enforcement.
The agreements ran with the US Attorney's office and with authorities in Massachusetts, Oklahoma and Florida. The agencies behind the case were the Drug Enforcement Administration, the Massachusetts State Police, the Criminal Investigation division of the Internal Revenue Service and the Boston Police Department. The prosecutors were Assistant US Attorneys Fred M. Wyshak Jr., Brian T. Kelly and James D. Herbert of the Organized Crime Strike Force Unit.
The state cases followed in 2001. On March 14, 2001, prosecutors in Tulsa County charged Martorano, Bulger and Flemmi in the Wheeler case. Martorano was charged with first-degree murder and conspiracy to commit murder, with the charge to be reduced to second-degree murder if he cooperated and a 15-year term to follow. Oklahoma prosecutors said they would seek the death penalty against Bulger and Flemmi, but not against Martorano. In both Oklahoma and Florida he had faced a possible death sentence when he chose to cooperate.
In March 2001 he pleaded guilty in Florida to second-degree murder in the Callahan case, again agreeing to testify against Bulger and Flemmi in exchange for the reduced charge.
On May 3, 2001, he appeared in Tulsa and pleaded guilty to the second-degree murder of Roger Wheeler under his plea agreement. He was 60. Asked for his plea, he answered "guilty." The Oklahoma sentence was 15 years.
The federal sentence came later than the plea, after years of testimony. On June 24, 2004, Judge Wolf formally accepted the guilty plea and sentenced Martorano to 14 years in prison, followed by five years of supervised release. The Oklahoma and Florida sentences of 15 years each were to run concurrently with the federal term. He served his time in a special facility for government witnesses. He did not appeal.
At the sentencing he apologized to the families of the people he had killed. Some of the relatives did not receive the apology well.
US Attorney Michael J. Sullivan defended the bargain while making no excuse for the man. "Martorano is a criminal who committed numerous unspeakable acts of violence," he said, adding that Martorano's "decision to cooperate, literally opened the floodgates." He said he hoped "the victim families and the public understand the horrible dilemma we in law enforcement faced in this case." Prosecutors credited Martorano's cooperation with helping to convict former FBI agent John Connolly, former State Police Lieutenant Richard Schneiderhan and Stephen Flemmi.
The former FBI agent John Connolly was convicted in federal court in Boston in 2002, and the First Circuit affirmed that conviction on August 14, 2003, in an opinion that drew on Martorano's account of how Connolly had passed information to the gang.
In 2008 Connolly went on trial in Miami for the Callahan murder, and Martorano testified there as well. Connolly was convicted of second-degree murder and sentenced to 40 years. On May 28, 2014, Florida's Third District Court of Appeal voided that conviction in a 2-1 decision, with the ruling stayed for further appeal.
Martorano left federal prison in March 2007, after about 12 years in custody counted from his capture in 1995. He was 66. He declined to enter the witness protection program and went back to the Boston area.
The terms of his cooperation drew criticism once he was free. The government paid him $20,000 after his release. Connolly's lawyer, Manuel Casabielle, said in January 2008: "they are paying him for his testimony, past, present and future."
In 2008 he gave a television interview to Steve Kroft in which he rejected the word informer. "One's got the courage to stand on the stand," he said, "the other ones are doing it behind your back and dropping dimes." In the same interview he described himself as a government witness, not a rat.
Bulger's trial opened in US District Court in Boston in June 2013. Martorano, then 72, was the first of Bulger's top former associates to take the stand, beginning on June 17, 2013.
He told the jury that he had gone along with Bulger and Flemmi "because they were my partners." "We were up to our necks in murders," he said. He described his shock at learning that both men had been informing for the FBI, and said it was that discovery that turned him toward the government.
Brennan cross-examined him on June 18 and 19. He pressed Martorano on the money he had made since his release: he said he received Social Security, about $70,000 from a book about his life and $250,000 from a film company, with up to $250,000 more to come if a film were made. Brennan also pressed him on the varying stories he had told over the years. Martorano admitted that he had once lied to a state trooper about one of the killings. "I recanted that," he said. Bulger's other lawyer, J.W. Carney Jr., said prosecutors had "basically threw their hands up in the air and said, 'Take anything you want.'"
On redirect, Wyshak took him through 11 killings one at a time, and Martorano confirmed Bulger's involvement in each.
In August 2013 the jury convicted Bulger on 31 of 32 counts, including 11 of the 19 murders charged. On November 14, 2013, US District Judge Denise Casper sentenced him to two consecutive life terms plus five years and ordered $19.5 million in restitution.
After the sentencing, the families of the dead spoke about the men who had gone free. The niece of one of Bulger's victims called the freedom of Martorano and of another former associate, Kevin Weeks, "ludicrous." "I don't think there will ever be justice," she said. Prosecutor Brian Kelly answered the criticism directly: "By pleading guilty, he doubled his time in prison." Wyshak said the Martorano deal had "brought Weeks to the table."
Bulger's appeal to the First Circuit put Martorano's deal at its center. Bulger argued that the government had made an off-the-books promise that Martorano would not have to testify against his own brother, Howard Winter or another associate. The court found the evidence for that "hardly conclusive" and noted that the written plea agreement contained an integration clause.
Bulger also pointed to an anonymous letter of October 2012 alleging that Martorano had been gambling illegally and that a State Police handler had blocked any inquiry. The State Police found the allegation unfounded, and Martorano said he had simply gambled with a friend at a casino. The court did not treat Martorano as a clean witness. The jurors, it said, "had plenty of reasons to question his veracity."
In June 2013 Martorano was living in Massachusetts, where the local police chief said he was not on parole and could live where he pleased.
The case against Bulger and Flemmi leaned on cooperating witnesses who had taken part in the gang's crimes. Martorano was the first of Bulger's top associates to make such an agreement and the first to testify against him at trial. His federal plea agreement, made with the US Attorney's office, was matched by agreements with authorities in Massachusetts and in the two states where Wheeler and Callahan died. The price of the bargain was set out by the First Circuit: his cooperation was required against Bulger, Flemmi and corrupt members of law enforcement, and in return he received a fourteen-year federal sentence. His pleas to second-degree murder in Oklahoma and Florida spared him the death penalty that prosecutors in Tulsa said they would seek against Bulger and Flemmi.
The same prosecutions exposed how the FBI had handled Bulger and Flemmi as informants. Judge Wolf's decisions of 1999 dealt with that relationship at length, and the federal courts later found that some FBI members had impeded the Wheeler and Callahan investigations to protect the two men. Connolly's federal conviction, his Florida murder conviction and its later reversal, and Bulger's own trial all drew on Martorano's account.
Only 12 of the 20 killings Martorano admitted rest on convictions: the ten federal murders and the two state cases. The eight further Massachusetts murders detailed under his plea agreement, and the eight killings he placed in the 1960s, are admissions only and were never tried.
His motive is contested. He said he never killed for money and called himself a vigilante rather than a serial killer. Prosecutors said he acted on the orders of Bulger and Flemmi in the Wheeler and Callahan cases, and the First Circuit described him as possibly the head of the gang's enforcement division.
His reliability as a witness was challenged at every trial. Defense lawyers pointed to the payments he received after his release, the money from a book and a film company, a lie he admitted telling a state trooper, and the varying stories he had told over the years. The First Circuit noted the claim of an unwritten promise in his deal and found it unproven.
About 1940 or 1941: John V. Martorano is born.
1960s: Eight killings later admitted by Martorano, never charged.
1973 to 1976: Ten murders in Massachusetts later charged in the federal Superseding Information.
1979: Martorano is indicted on federal racketeering charges with Howard Winter and becomes a fugitive.
May 27, 1981: Roger Wheeler dies in Tulsa, Oklahoma.
August 1, 1982: John B. Callahan dies in Florida.
January 1995: Martorano is taken into custody in Florida.
August 1995: He is indicted in Boston on racketeering and related charges.
1998: He begins plea negotiations with federal prosecutors.
September 9, 1999: He agrees to plead guilty and testify against Bulger and Flemmi.
September 30, 1999: He pleads guilty in US District Court, Boston, to the Superseding Information.
March 14, 2001: Tulsa County prosecutors charge him with first-degree murder and conspiracy to commit murder in the Wheeler case.
March 2001: He pleads guilty in Florida to second-degree murder in the Callahan case.
May 3, 2001: He pleads guilty in Tulsa to the second-degree murder of Roger Wheeler.
August 14, 2003: The First Circuit affirms John Connolly's federal conviction.
June 24, 2004: Judge Mark L. Wolf sentences Martorano to 14 years and five years of supervised release.
March 2007: He is released from federal prison.
2008: He testifies at Connolly's murder trial in Miami; Connolly is convicted of second-degree murder and sentenced to 40 years.
June 17 to 19, 2013: He testifies at Bulger's trial in Boston.
August 2013: Bulger is convicted on 31 of 32 counts, including 11 murders.
November 14, 2013: Bulger is sentenced to two consecutive life terms plus five years.
May 28, 2014: A Florida appeals court voids Connolly's murder conviction, 2-1.