By Chuck Strouse
By Scott Fishman
By Terrence McCoy
By Ryan Yousefi
By Ciara LaVelle, Kat Bein, Carolina Del Busto, and Liz Tracy
By Pepe Billete
By Ryan Yousefi
By Kyle Swenson
Meanwhile Whitey's criminal enterprise loan-sharking, extortion, drug-dealing, bookmaking, murders of assorted underworld figures continued without a hitch. His influence flourished to some degree because the Italians had been rendered impotent. And since Whitey also snitched on other, minor hoods in Southie, his competition was reduced.
Other law enforcement agencies tried to investigate and wiretap Whitey, but the operations always inexplicably failed. Whitey and Flemmi seemed untouchable. Many cops around Boston wondered just what kind of information was passing between the FBI and Whitey. "People suspected Connolly had a relationship with Flemmi and Bulger," commented the anonymous Massachusetts lawman. "There was no constraints put on him whatsoever in the handling of those informants."
But Connolly didn't operate in a vacuum, the official added. "There were a lot of others in the agency who enabled him."
One of Connolly's superiors, John Morris, was one such enabler. He would later testify that he hosted several dinner parties at his house for Connolly, Whitey, and Flemmi. Often, Morris said, they would all exchange gifts: a bottle of wine (Whitey nicknamed Morris "Vino") or $1000 in cash (so Morris could fly his girlfriend to meet him during an FBI conference).
This cozy situation might have continued in Boston if Whitey and Flemmi hadn't decided to expand their empire to Miami.
By day John Callahan worked as an accountant at a legitimate firm in Boston. By night he partied with gangsters including Whitey Bulger and Steve Flemmi. He was a tall, burly guy who was married to a nice girl in the suburbs and had two little kids. Like Whitey, he was Irish. And like Whitey, he had grown up in a working-class home just outside Boston. He also excelled at sports at one time, he had been an Olympic weightlifter.
According to public records, around 1980, Callahan was skimming money and laundering cash for Whitey through one of his accounts World Jai-Alai, based in Miami. (It is now called Miami Jai-Alai.) Back then, it was owned by a rich investor named Roger Wheeler, who lived in Oklahoma. Wheeler trusted the people working for him because many were former federal agents. "I feel comfortable surrounded by FBI types," he told the Miami Heraldin 1979. "We have six in the company here."
By 1981, Wheeler suspected that something shady was going on and called for an audit of the business's books.
Halloran was a Boston street hustler, an alcoholic cokehead who did jobs for Whitey and occasionally the Italians. He told authorities that Callahan had offered him $20,000 to kill Wheeler, but he had declined the job.
He also implicated Whitey and Flemmi, and claimed to have information tying them to other murders. Some FBI agents not Connolly wanted to put Halloran in the witness protection program, but the request was denied. The cokehead didn't have enough evidence, FBI brass said.
Then in May 1982, Whitey and Flemmi gunned down Halloran in a spectacular midday ambush outside a Southie bar. Whitey drove a souped-up blue Chevy fitted with a smoke screen and an oil slick; he wore a light brown wig and a floppy mustache. It would later become clear that he liked wearing disguises when he killed people.
Soon cops in two states began looking for Callahan. At first, prosecutors contend, Connolly blocked access to the accountant. Then, they allege, he told Whitey and Flemmi that the Yale grad would "fold" and implicate them in the murders.
In court papers and through his lawyers, Connolly denies this. He claims he merely pumped his sources for information about the Halloran murder. The FBI agent had never even met Callahan; he had spoken to him on the phone once.
Indeed during this time, Connolly was attending a master's degree program at Harvard's Kennedy School of Government. The agent was well liked by the other, bookish graduate students; they were awed when, after class, he would hold secret meetings with his gangster informants in Harvard Square. Connolly was elected president of his class an unlikely role for a man plotting a murder.
John Martorano was one of Whitey's foot soldiers. He was a thick-faced, pug-nosed, stocky guy born in a Boston suburb in 1940. School wasn't easy for him he was dyslexic but he became captain of the Milton High football team. His athletic prowess would take him nowhere, though. He fell in with mobsters, who recognized his one shining talent: killing. He murdered a man for the first time when he was 24 years old. Dozens more corpses would follow.
Sometime at the end of July 1982, Whitey and Flemmi summoned Martorano to New York for a meeting. Callahan, the corrupt accountant, had to go, they said.
Martorano, in an uncharacteristic plea for mercy, argued that Callahan's life should be spared. He was a friend who often let the assassin stay at his South Florida condo.