Stephen Flemmi was a leader of the Winter Hill Gang, an organized crime group that controlled extortion, drug dealing and other rackets in South Boston and the wider Boston area from the early 1970s to the mid-1990s. He ran it with James Bulger. On October 14, 2003, at the age of 69, he appeared before Judge Richard G. Stearns in federal court in Boston and pleaded guilty to all counts of a superseding indictment, which covered ten murders committed between 1974 and 1985. On January 27, 2004, Judge Stearns sentenced him to life. On September 30, 2004, a court in Tulsa, Oklahoma, imposed a second life sentence for the 1981 murder of Roger Wheeler. A third followed in Florida, for the 1982 murder of John Callahan in Miami.
The pleas were part of a bargain. Prosecutors in Oklahoma and Florida, where both murders carried the death penalty, agreed not to seek it, and Flemmi gave them evidence against a retired FBI agent, H. Paul Rico, whom he named as a participant in the planning of the Wheeler murder. Rico died in January 2004, before he could be tried. Flemmi was later a witness at the Miami trial of a second former FBI agent, John Connolly, in 2008, and at the federal racketeering trial of Bulger in Boston in 2013. In both he testified that he and Bulger had been informants for the FBI and that agents had protected the gang.
In a 1999 ruling in the District of Massachusetts, Judge Mark L. Wolf found that Flemmi had been exchanging information with the FBI since the early 1960s. In November 1965, Special Agent H. Paul Rico targeted him for development as a Top Echelon informant, the highest status a source can achieve, and developed him as an asset against the Patriarca Family, the Mafia organization in New England. Rico rated the information he supplied as excellent.
An indictment against Flemmi that was dismissed in 2001 alleged that he and a co-defendant, Francis Salemme, had been close associates since at least 1967. Among its racketeering acts were four murders in 1967 and an attempted murder in January 1968, all alleged and none ever tried. Judge Wolf found that in 1969 Rico told Flemmi and Salemme that they were about to be indicted for the attempted murder and suggested they leave, and both did. The indictment alleged that Flemmi was a fugitive from about 1969 to 1974, and the court found that during that time he stayed in touch with Rico, who did not tell the agents investigating the flight about those contacts. In 1974, at Rico's request, Flemmi returned to Boston. As Rico had promised, the court said, he was released on bail at once and the charges against him were dropped.
The indictment described what followed. About 1974, it alleged, Raymond L. S. Patriarca, the head of the Patriarca Family, offered Flemmi made membership. Flemmi declined and aligned himself with Howard Winter, John Martorano and Bulger of the Winter Hill Gang, while pledging loyalty to Patriarca. After Winter was convicted around 1979, the indictment said, Bulger and Flemmi succeeded him as the leaders of the gang. Its business was loan-sharking, drug dealing and gambling, and federal prosecutors said it controlled extortion, drug dealing and other rackets in South Boston and the greater Boston area into the mid-1990s.
Judge Wolf said in 2001 that Flemmi had been able to commit the crimes charged largely because of the protection of the Federal Bureau of Investigation. The first of the ten murders to which Flemmi later pleaded guilty, that of James Sousa, is dated October 1974, the year of his return to Boston.
The ten murders to which Flemmi pleaded guilty, as federal prosecutors listed them at his sentencing on January 27, 2004, ran from 1974 to 1985. Some of the dates are approximate.
James Sousa died in October 1974. Edward Connors died on June 12, 1975, and Thomas King on November 5, 1975. Richard Castucci died on December 30, 1976. Roger Wheeler died in Tulsa on May 27, 1981. Debra Davis died in late 1981. John Callahan died in Miami on August 1, 1982. Arthur Barrett died in August 1983, John McIntyre on November 30, 1984, and Deborah Hussey in early 1985.
When he pleaded guilty on October 14, 2003, federal prosecutors set the killings in the context of the gang's history. Some of them, they said, belonged to the early 1970s conflict between Winter Hill and a rival group led by Al Notorangeli, and to the consolidation of the gang's control in South Boston later in the decade. Others they described as witness-elimination killings, among them those of Castucci, Callahan and McIntyre. Debra Davis and Deborah Hussey were young women, each 26 years old, and prosecutors said Flemmi pleaded guilty to murdering them together with Bulger.
At Bulger's trial in July 2013, Flemmi gave reasons for some of the deaths. He said that he and Bulger had been responsible for the death of Connors in 1975 after Connors was talking about gang business. He said that Castucci had been killed by Martorano at the request of the gang's leaders. He said that Davis died because she knew the gang was trading information for protection with Boston FBI agents, and that he had agreed she had to die. "It's affected me and it's going to affect me until the day I die," he told the jury.
Roger Wheeler, 55, was the chairman of Telex Corporation, based in Tulsa, and had bought the company World Jai Alai. He was killed in Tulsa on May 27, 1981. Prosecutors said the gang wanted control of World Jai Alai and that Wheeler had come to suspect Flemmi and Bulger of skimming money from it. The company's security chief at the time was Rico, who had retired from the FBI in 1975.
The early Tulsa investigation went cold. A police sergeant, Mike Huff, who was 25 at the time of the killing, arrested Rico about 22 years later. Wheeler's son said that Rico had been a suspect of Huff's since 1982, and that the arrest in 2003 was a milestone in a 22-year effort to get justice for his father.
Martorano, who by 2001 had admitted his part, agreed to cooperate. In May 2001 he pleaded guilty in the Wheeler case to second-degree murder. He testified that Flemmi and Bulger ordered the killing and that Rico helped by giving the gang details of Wheeler's schedule. Rico denied any involvement.
Flemmi said that in a telephone call in May 1981 Rico had confirmed that he and others wanted Wheeler killed. He also said that he and Martorano met Rico in Miami more than a year after the killing to talk about money they had been promised, and that Rico told them none was available because the planned purchase of World Jai Alai never went ahead.
John Callahan, 45, was a former president of World Jai Alai. He died in Miami in 1982. At Connolly's trial, gang members testified that Callahan was killed after Connolly told the Boston gang that Callahan might implicate them in the 1981 murder of the Oklahoma man.
In 2005 a Miami-Dade County grand jury indicted Connolly in the case. The indictment alleged that Connolly conspired to kill Callahan and that Bulger, Flemmi and Martorano carried it out. The state attorney, Katherine Fernandez Rundle, said Connolly's information had been the guiding hand that led to the deaths.
The original federal racketeering indictment was returned in January 1995. It charged Flemmi and Bulger with racketeering and racketeering conspiracy, and the racketeering acts it listed included murder. Bulger fled Boston and remained a fugitive until 2011, when he was arrested in Santa Monica, California. Flemmi was held.
The warning that indictments were coming was later traced to the FBI. At Connolly's trial in 2002, a Bulger associate testified that in late December 1994 Connolly told Bulger, Flemmi and Salemme that indictments were about to come down. Connolly, who had retired from the FBI in 1990, was convicted by a Boston jury on May 28, 2002 on four of five counts, including racketeering, obstruction of justice and lying to the FBI. On September 16, 2002, Judge Joseph L. Tauro sentenced him to more than ten years. Connolly denied wrongdoing and said his dealings with the informants had been approved by his FBI supervisors.
On September 28, 2000, a 32-count federal indictment was unsealed in Boston against Bulger, Flemmi and an associate, Kevin P. O'Neil. It charged racketeering, racketeering conspiracy, extortion, money laundering and other crimes, and it alleged that the gang had taken part in 21 murders, 18 of them with Bulger's participation and ten with Flemmi's. It alleged that the gang conspired to kill Wheeler to gain control of World Jai Alai.
Flemmi's position in the original case rested on his status with the FBI. On August 21, 2001, before Judge Wolf, he pleaded guilty to a superseding information charging six counts of extortion and one count of money laundering conspiracy. The agreement was a binding plea under Rule 11(e)(1)(C). It carried 120 months on each count, to run concurrently, a special assessment of $400 and forfeiture. The court dismissed the Fourth Superseding Indictment, with its racketeering and racketeering conspiracy charges, with prejudice. Judge Wolf called those charges fundamentally flawed and said it was inconceivable to him that the case would have been brought by a properly informed prosecutor. He added that Flemmi had substantial authorization defenses and that he doubted anything of institutional importance had been achieved by the case.
The murder charges against Flemmi remained pending before Judge Stearns, and trials in Oklahoma and Florida were contemplated.
Prosecutors in Tulsa filed charges on March 14, 2001. Bulger, Flemmi and Martorano were each charged with first-degree murder and conspiracy to commit murder in the death of Wheeler. District Attorney Tim Harris said he would seek the death penalty against Bulger and Flemmi. Martorano's charge was to be reduced to second-degree murder if he testified, with a 15-year term, and Harris said the Oklahoma case would probably not go to trial until the Boston charges were resolved.
In Boston, on July 17, 2001, Flemmi pleaded not guilty to 17 charges, including ten murders, racketeering, extortion, money laundering, obstruction of justice, perjury and evidence tampering. The penalty, if he was convicted, was life. Assistant U.S. Attorney Brian Kelly expected to call about 50 witnesses at a trial of about six months, to begin the following year. The arraignment had been delayed for nearly ten months because more than 40 Boston-area lawyers had declined the case and Flemmi said he could not afford counsel; an assistant federal defender was assigned in late June. Oklahoma and Florida both had the death penalty, and he faced separate state murder charges in each: the 1981 Wheeler case in Tulsa and the 1982 Callahan case in Miami.
Earlier in October 2003 Flemmi had begun to cooperate with prosecutors. In exchange for his help in the Wheeler case, Tulsa's district attorney made what he called a measured and calculated decision to drop the pursuit of the death penalty. Florida prosecutors did the same in the Callahan case. The agreement allowed prosecutors in Tulsa to charge Rico, then 78, with murder and conspiracy, and he was arrested in Florida that week.
Flemmi came before Judge Stearns on October 14, 2003. He pleaded guilty to all counts of the superseding indictment, 17 counts in all. The government said it would recommend the maximum federal penalty possible, life, and that Flemmi would plead guilty to first-degree murder charges in Florida and Oklahoma. The indictment also covered offenses that were not murders: trafficking in cocaine and marijuana, extortion of drug dealers, bookmakers and loan sharks, the collection of debts by extortion, money laundering through the South Boston Liquor Mart and the Rotary Variety Store, perjury in testimony given in August 1998 in a related case, and obstruction of justice.
Prosecutors described the killings in court while relatives of the dead watched. A brother of one victim was removed from the courtroom after he shouted at Flemmi. Flemmi, speaking to the court, apologized to the victims' families, the public and the court. "I truly am sorry," he said. The U.S. Attorney, Michael Sullivan, said Flemmi might supply information that would lead to more indictments.
Judge Stearns sentenced Flemmi on January 27, 2004 to life. The case had been prosecuted by Assistant U.S. Attorneys Fred M. Wyshak Jr., Brian T. Kelly and Colin Owyang of the Organized Crime Strike Force Unit in the office of U.S. Attorney Michael J. Sullivan. The investigation had involved the DEA, the Massachusetts State Police, IRS Criminal Investigation, the Boston Police Department and other agencies.
Rico had died in Tulsa on January 16, 2004, while awaiting trial. He had denied any part in the Wheeler murder and was never tried.
On September 30, 2004, Flemmi was sentenced to life in Tulsa for the Wheeler murder, under the plea agreement that spared him the death penalty. Martorano, who pleaded guilty to second-degree murder in the Wheeler case, was sentenced to 14 years. In Florida, Flemmi received a life sentence for the Callahan murder.
In 2008 Flemmi testified at Connolly's trial in Miami. He said that Connolly had protected the gang from prosecution and passed along information about suspected informants within its ranks. On November 6, 2008 the jury convicted Connolly of second-degree murder in the death of Callahan and acquitted him of conspiracy.
Flemmi's most extended testimony came at Bulger's racketeering trial in Boston. Bulger had fled Boston in the mid-1990s and was arrested in Santa Monica in 2011. He faced 32 counts, including 19 murders. Flemmi, then 79, began testifying on July 18, 2013. Prosecutor Fred Wyshak asked about his relationship with Bulger, and he answered, "Strictly criminal."
He told the jury that he and Bulger had been FBI informants and had met agents hundreds of times, giving information about the New England Mafia and smaller South Boston criminals, in what he called a quid pro quo relationship in which Bulger took the lead. He said Bulger had organized drug dealing in South Boston, from which Flemmi earned a substantial amount of money over time. He said Bulger had introduced him to Connolly in 1975 and that Connolly's warnings, passed on through Bulger, helped the gang avoid investigations. He also said the gang paid Connolly about $230,000 in cash over 15 years and paid five other Boston FBI agents. On one day he showed diagrams he had drawn for the FBI, marking places where the rival Mafia gathered.
He described nine killings that Bulger ordered, approved or carried out, among them Connors, Davis and Hussey, and he also described the death of Brian Halloran. Bulger's lawyer cross-examined him. Under that questioning Flemmi accepted that he had lied in court before; he said he had done so to protect his corrupt relationship with the FBI and that he was telling the truth now. The defense also pointed to differences between his 2013 account of how Davis and Hussey died and what he had said at earlier trials. Flemmi called them inadvertent mistakes.
On August 12, 2013, the jury convicted Bulger of racketeering conspiracy and other offenses and found that he had played a role in eleven murders: Deborah Hussey, Paul McGonagle, Edward Connors, Thomas King, Richard Castucci, Roger Wheeler, Brian Halloran, Michael Donahue, John Callahan, Arthur Barrett and John McIntyre. It made no finding on the death of Davis. In November 2013 Bulger was sentenced to two consecutive life terms. Bulger's lawyers had acknowledged his involvement in gambling and loan-sharking but challenged the credibility of witnesses who had received lighter sentences.
In July 2021, citing his age, Flemmi wrote to a judge in Oklahoma asking for release. On August 18, 2021, the Florida Commission on Offender Review heard his petition for early release by conference call and voted 3 to 0 to deny it. Flemmi, then 87, did not speak. His daughter urged the commissioners to release him, saying he had shown remorse. Davis's brother was the only person who spoke against parole and told the commissioners that Flemmi did not deserve to breathe.
The commission said Flemmi could apply again in seven years, when he would be 93, and estimated that he would finish his federal sentence on May 4, 2218. As of August 2021 he was held in federal custody, serving life sentences imposed by a federal court and by courts in Oklahoma and Florida.
Three features of the legal setting explain how a man charged with ten murders came to be sentenced in three courts by agreement.
The first is the FBI's Top Echelon Informant program. Judge Wolf found in 1999 that Rico had targeted Flemmi for that status in 1965. In 2001 he said that the racketeering charges were flawed partly because Flemmi and Bulger had been Top Echelon informants during the period charged, and he noted an FBI review that had concluded Flemmi was at least tacitly authorized to take part in policy-making of the Mafia. Those findings were the background to the dismissal of the racketeering indictment in August 2001.
The second is the federal racketeering statute. The 2000 indictment charged Flemmi with racketeering conspiracy under 18 U.S.C. 1962(d) and racketeering under 18 U.S.C. 1962(c), and with extortion under 18 U.S.C. 1951. The indictment set out murders, including those of 1967 and 1968, as racketeering acts of the alleged enterprise.
The third is the form of the pleas. The August 2001 agreement was a binding plea under Rule 11(e)(1)(C), which fixed the 120-month term when the court accepted it. The 2003 agreement was a package across three jurisdictions: Oklahoma and Florida, where the death penalty was available, gave it up in return for Flemmi's evidence against Rico, and the U.S. Attorney said further indictments might follow.
Bulger has denied that he was an FBI informant, and his defense told the 2013 jury that agents, including Connolly, had tipped him off. Flemmi's testimony that both men were informants was given as a cooperating witness who had already been sentenced to life and had avoided the death penalty by cooperating.
Flemmi accepted under cross-examination that he had lied in court before. Bulger denied killing Davis and Hussey. The Bulger jury made no finding on Davis's death.
The four murders of 1967 and the attempted murder of 1968 in the earlier indictment were never tried and were dismissed with prejudice on August 21, 2001. They are allegations only. The charges brought against Flemmi in 1968 had been dropped in 1974.
Rico, charged in Oklahoma, denied any part in the Wheeler murder and died before trial. The allegations about his role come from Martorano and Flemmi.
Flemmi's statement that the gang paid Connolly about $230,000 and five other agents was testimony; Connolly denied wrongdoing.
November 1965: Special Agent H. Paul Rico targets Flemmi for development as a Top Echelon informant.
1967: four murders alleged as racketeering acts in the later indictment (dismissed 2001).
January 1968: an attempted murder alleged in the same indictment.
1969: Rico tells Flemmi and Salemme they are about to be indicted; both leave Boston.
1974: Flemmi returns to Boston at Rico's request; released on bail, charges dropped.
October 1974: James Sousa dies, the first of the ten murders.
1975: Edward Connors (June 12) and Thomas King (November 5) die.
December 30, 1976: Richard Castucci dies.
About 1979: Bulger and Flemmi succeed Howard Winter as leaders of the Winter Hill Gang.
May 27, 1981: Roger Wheeler dies in Tulsa.
Late 1981: Debra Davis dies.
August 1, 1982: John Callahan dies in Miami.
August 1983: Arthur Barrett dies.
November 30, 1984: John McIntyre dies.
Early 1985: Deborah Hussey dies.
January 1995: racketeering indictment returned against Flemmi and Bulger; Bulger flees.
September 28, 2000: 32-count indictment unsealed in Boston.
March 14, 2001: Tulsa prosecutors charge Bulger, Flemmi and Martorano with first-degree murder in the Wheeler case.
July 17, 2001: Flemmi pleads not guilty to 17 charges in Boston.
August 21, 2001: guilty plea to seven counts before Judge Wolf; 120 months; the 2000 indictment is dismissed.
May 28, 2002: Connolly convicted in Boston.
October 14, 2003: guilty plea to all counts of the superseding indictment before Judge Stearns.
January 16, 2004: Rico dies in Tulsa.
January 27, 2004: sentenced to life in Boston.
September 30, 2004: sentenced to life in Tulsa.
November 6, 2008: Connolly convicted in Miami after Flemmi's testimony.
July 18 to 24, 2013: Flemmi testifies at the Bulger trial.
August 12, 2013: Bulger convicted.
August 18, 2021: Florida Commission on Offender Review denies Flemmi parole, 3 to 0.