Crime Library: Criminal Minds and Methods

James 'Whitey' Bulger

The Whitey Plague

Whitey was on a tear, and Special Agent Connolly covered for him at every opportunity. When Oklahoma investigators working the Wheeler case asked for photos of Bulger and Flemmi to show to potential witnesses, Connolly refused, saying that his TEs had declared their innocence and that was good enough for him. These investigators pressed for Bulger and Flemmi to take polygraph tests, and again Connolly shielded his informants. He finally relinquished photos only after his superiors threatened to drop Bulger and Flemmi from the Top Echelon Informant Program if he didn't comply. But thanks to Connolly, Bulger and Flemmi escaped indictment for any of their murders. Connolly and his supervisor John Morris convinced their superiors that Bulger and Flemmi were indispensable in their quest to topple the Mafia in Boston. And so the Whitey Bulger plague continued.

Connolly in particular treated Bulger like a star, and over time the stardust started to rub off on Connolly himself. Now wearing flashy double-breasted suits and styling his hair in a John Gotti-like blow-dry, he looked more like a wiseguy than a Southie guy, and fellow agents jokingly referred to him as "John Cannoli."

In the early 1980s Connolly and Morris skewed their reports on Bulger to enhance his value as an informant. Morris later admitted under oath that he and Connolly also gave Bulger and Flemmi advance warning whenever they learned that other agencies were investigating the two gangsters. Morris and Connolly were in deep with the bad guys, and Morris had even accepted bribes from Bulger, "mad money" for Morris's burgeoning affair with his secretary that came in envelopes delivered by Connolly.

But as informants, Bulger and Flemmi were far less valuable than their handlers made them out to be. It was true that Bulger and Flemmi knew Jerry Angiulo and his four brothers, had had meetings with them, and had even been to Angiulo's headquarters at 98 Prince Street in Boston's North End. But the information they provided was nothing the FBI didn't already know. Bulger and Flemmi had been asked to find out if 98 Prince Street had an alarm system, but they never found out for sure. Flemmi made a rough sketch of Angiulo's office for the feds, but they already had the layout of the building. Flemmi knew a bit more about Angiulo's headquarters than Bulger did because he'd been courted by the Mafia for years, but what he knew didn't amount to much.

Gerry Angiulo
Gerry Angiulo

The real source of usable information was an anonymous disgruntled bookie who worked for the Angiulo organization. This nondescript bookie, according to the Boston Globe, "hated Angiulo for his greed and crude ways, his lack of loyalty to the real money men - the bookmakers." A frequent visitor to 98 Prince Street, this bookie not only provided information about the building itself, he revealed the ins and outs of the Mafia's gambling operations.

With the help of this information, six FBI agents broke into 98 Prince Street in January 1981 and planted two listening devices in the walls, connecting them to batteries concealed above the ceiling. The feds listened in on the Mafia's business for four months, getting details on loan-sharking and gambling operations that earned "$45,000 a day in gross receipts." The FBI built a case that eventually resulted in 23 convictions, including Jerry Angiulo and two of his brothers.

But when the FBI reports on the case were written, Bulger's and Flemmi's guardian angels made sure that their favorite informants were given a starring role in the investigation. Connolly and Morris acknowledged that Bulger and Flemmi were far from upstanding citizens, but they argued that when compared to the Mafia, Whitey and Stevie were minor threats and should be kept on as informants. With Angiulo's empire in ruins, Whitey Bulger soon became the undisputed top dog of Boston's organized-crime scene. His rackets grew, and with his FBI protectors running interference for him, the city was his to exploit.

Ilario  Zannino
Ilario Zannino

Bulger formed alliances with Mafia members who had escaped the Angiulo convictions, and the state police observed several made men paying regular visits to Bulger at the Lancaster Street garage, showing him the kind of respect reserved for a don. The man who succeeded Angiulo as boss, "Cadillac Frank" Salemme, was willing to work hand-in-hand with Bulger.

Frank Salemme
Frank Salemme

In a bugged conversation that took place in April 1981, Mafia underboss Ilario Zannino warned a deadbeat gambler that he'd better pay an $80,000 debt to Bulger and Flemmi because "they're with us." According to the Boston Globe, Zannino then turned to his legbreaker, who was standing nearby, and asked, "Are they with us? Are they with us?"

"A thousand percent," the legbreaker answered.

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