Throughout the 1980s, Bulger, Flemmi and Weeks operated rackets throughout
Eastern Massachusetts including loansharking, bookmaking, truck hijacking,
arms trafficking and
extortion. State and federal agencies were repeatedly stymied in their attempts to build cases against Bulger and his inner circle. Among the reasons for this was the trio's fear of wiretaps and their strict protocol of never discussing business over the telephone or in vehicles. Other reasons included South Boston's code of silence and
corruption within the FBI, the MSP and the BPD. Although Connolly was Bulger's most infamous source inside law enforcement, Weeks has stated that MSP lieutenant
Richard J. Schneiderhan, the crew's only source inside that agency, was valued more highly. Bulger formed alliances with members of the Patriarca family who had escaped the conviction that sent the Angiulo brothers to prison. In 1984, Bulger acquired Stippo's Liquor Mart adjacent to the Old Colony Housing Project by forcing the proprietor, Stephen "Stippo" Rakes, to sell him the business at gunpoint for $67,000. Bulger renamed the business the South Boston Liquor Mart and used the backroom as his gang's primary headquarters. He also forced local bars to buy alcohol from this business.
World Jai Alai Winter Hill associate John "Jack" Callahan was fired from his role as president of World Jai Alai (WJA), a
parimutuel betting company which operated in
Connecticut and
Florida, after he lost his gaming license in Connecticut due to his associations with organized crime. Callahan subsequently
conspired with former FBI agent
H. Paul Rico, who had served as Callahan's head of security at WJA, and Richard P. Donovan, another former WJA president, to regain control of the company by purchasing the business from its owner, Tulsa businessman Roger Wheeler. Callahan offered Bulger, Flemmi and Martorano a $10,000 per week "
skim" from the parking and concession proceeds at WJA's
fronton in
Hartford, Connecticut, if the Winter Hill Gang would protect WJA against interference by the Mafia, to which the gangsters agreed. Wheeler refused to sell WJA to Callahan and his associates, who agreed that Wheeler had to be killed. Fearing that Wheeler was on the verge of reporting the skimming operation to authorities, Bulger ordered his murder. On May 27, a disguised Martorano, using guns shipped by bus from Bulger and Flemmi, killed Wheeler by shooting him in the face in the parking lot of the Southern Hills Country Club in Tulsa. After Connolly told Bulger in July 1982 that the FBI wanted to question Callahan in connection with Wheeler's murder, he and Flemmi decided to kill Callahan. On August 1, Martorano lured Callahan into a car and shot him in the head during a meeting at
Fort Lauderdale International Airport. With the assistance of
Joe McDonald, Martorano left the body in the trunk of Callahan's leased
Cadillac in a garage at
Miami International Airport. Allowing Callahan's body to be discovered went against Bulger's plans, however, leading him to complain about Martorano: "There's plenty of sand down there. He should have got off his fat ass and buried him!" Michael Solimando, Callahan's business partner, was summoned to Triple O's and told by Bulger that he was now responsible for a fictitious debt that Callahan had purportedly owed him. Bulger threatened Solimando, a bodybuilder, with a replica
Thompson submachine gun and said: "Your muscles aren't going to do you any good now." After flying to Switzerland and emptying Callahan's accounts, Solimando delivered $480,000 to the Winter Hill Gang, he made "a ton of money selling drugs," according to federal prosecutor Brian Kelly. Bulger became involved in
drug trafficking in 1981, While he profited from the distribution of
marijuana and cocaine, Bulger prohibited dealers from selling
heroin in South Boston. In April 1983, he learned that
Charlestown drug smuggler Joseph "Joe" Murray was importing marijuana into South Boston without the approval of the Winter Hill Gang and, in retaliation, tipped off Connolly about Murray's operations. Afterwards, Murray commenced monthly payments to Bulger for the privilege of warehousing his contraband in South Boston and for protection from the Winter Hill Gang. Bulger, Flemmi and Weeks were subjected to intense DEA surveillance in 1989 and 1990 but escaped being charged in the investigation. The DEA crackdown—which targeted three separate drug rings led by Shea, Paul Moore and Hobart Willis, each of whom reported to Bulger—effectively put Bulger's drug operations out of business. Shea quietly served a long prison sentence and refused to admit to having paid
protection money to Bulger, Flemmi and Weeks. Shea repeatedly got into fights with other inmates who accused Bulger of being "a rat," earning him a legendary reputation in South Boston. One such criminal was Arthur "Bucky" Barrett, a
safecracker and thief who allegedly participated in the theft of $1.5 million from the Depositors Trust bank in
Medford on Memorial Day Weekend of 1980. Barrett had refused to give Bulger a cut of the money from the heist, Immediately following the murder, Bulger reclined in a couch. Meanwhile, in the basement, Flemmi removed Barrett's teeth in the belief it would prevent later identification while Weeks and Patrick Nee dug a grave in the basement's dirt floor. Afterwards, Nee expressed anger that Barrett had been killed, expecting only an extortion to take place.
Arms trafficking During the most violent period of
the Troubles, sympathy for
Irish nationalism and the
Provisional Irish Republican Army (IRA) was common in South Boston, as were efforts to raise money and smuggle weapons for the IRA's
campaign against the
British presence in Northern Ireland. From the start of his involvement with the FBI, Bulger emphatically refused to betray the IRA.
Valhalla departed
Gloucester and rendezvoused off the west coast of Ireland with
Marita Ann, an IRA ship that had sailed from
Tralee. During the return voyage, the
Irish Navy stopped
Marita Ann and seized the hidden arsenal, arresting IRA members
Martin Ferris, Mike Browne and John Crawley. The operation had been compromised by IRA member
Sean O'Callaghan, an informant for the
Irish National Police. The seizure marked the complete end of any major attempt by the IRA to smuggle guns out of the U.S., which had largely ceased three years earlier with the arrest of their primary gunrunner,
George Harrison, by the FBI. The
United States Customs Service received notice of the weapons transfer and seized
Valhalla when it stopped in Boston on October 16, en route back to Gloucester. No weapons were found on the trawler, Quincy police then arranged for the FBI, the DEA, and the Customs Service to participate in McIntyre's debriefing. McIntyre implicated Bulger in the botched gunrunning to FBI Agent Roderick Kennedy, who was friendly with Connolly. After hearing of Kennedy's interview with a
Valhalla crew member, Connolly told Bulger of the cooperation. After McIntyre's disappearance, an FBI agent named Philip Brady told his family that he was likely murdered by the IRA. On September 5, 2006, Judge
Reginald C. Lindsay ruled that the mishandling of Bulger and Flemmi caused the murder of McIntyre, awarding his family $3.1 million in damages. Lindsay stated the FBI failed to properly supervise Connolly and "stuck its head in the sand" regarding numerous allegations that Bulger and Flemmi were involved in drug trafficking, murder and other crimes for decades.
Murder of Deborah Hussey In 1985, Bulger decided to kill Flemmi's 26-year-old stepdaughter, Deborah Hussey, who he regarded as a liability. Hussey knew about the Winter Hill Gang's dealings and had started going to a bar they frequented, where she indiscriminately named Bulger and Flemmi in conversation to acquire money from low-level gangsters who feared her stepfather. On January 14, 1985, Flemmi drove Hussey to East Third Street, which Bulger now nicknamed "the Hauntey," where Bulger strangled Hussey in the kitchen.
Massachusetts Lottery In the summer of 1991, Bulger and Weeks, along with associates Patrick and Michael Linskey, came into possession of a winning
Massachusetts Lottery ticket which had been bought at a store he owned. The four men shared a prize of around US$14 million. Bulger was widely thought to have obtained his share of the jackpot illegitimately.
Downfall After Connolly retired from the FBI in December 1990, Bulger and Flemmi were "closed" as informants as the Bureau no longer desired their services. In April 1994, a joint task force of the DEA, the MSP and the BPD launched a probe of Bulger's illegal gambling operations. The FBI, by this time considered compromised, was not informed. After a number of bookmakers agreed to testify to having paid protection money to Bulger, a federal case was built against him under RICO. According to Weeks: In 1995, Bulger and Flemmi were indicted on
racketeering charges along with two prominent Boston
mafiosi, Frank Salemme and Bobby DeLuca. During the discovery phase, Salemme and DeLuca were listening to a tape from a roving bug, which is normally authorized when the FBI has no advance knowledge of where criminal activity will take place. They overheard two of the agents who were listening in on the bug mention offhandedly that they should have told one of their informants to give "a list of questions" while speaking to the mobsters. When their lawyer, Tony Cardinale, learned about this, he realized that the FBI had lied about the basis for the bug in order to protect an informant. Suspecting that this was not the first time such a thing had happened, Cardinale sought to force prosecutors to reveal the identities of any informants used in connection with the case. Federal judge
Mark L. Wolf granted Cardinale's motion on May 22, 1997. On June 3, Paul E. Coffey, the head of the Organized Crime and Racketeering Section of the Department of Justice, gave a sworn statement admitting that Bulger had been an FBI informant. Coffey stated that since Bulger was accused of "leading a criminal enterprise" while working as an informant and was also now a
fugitive, he had "forfeited any reasonable expectation" that his identity would be protected. ==Fugitive==