Black Mass

As the new decade dawned, the Mafia was dissolving once again, and the Bulger-controlled Winter Hill gang was moving upscale and uptown. On both sides of the line, the key players began harvesting the fruits of the 1980s.

Whitey Bulger had legitimate income for the first time since he was a courthouse janitor.

Stevie Flemmi made $360,000 on the resale of his Back Bay building.

John Connolly landed a big job at a major utility.

Jeremiah O’Sullivan was charging $300 an hour as a defense lawyer at a white-shoe Boston firm. And the FBI’s Jim Ring soon followed him there as an investigator.

Only John Morris struggled as the decade began. He’d barely escaped the investigation of 75 State Street leaks to the Boston Globe. Regaining his balance, Morris moved on to Washington with an assist from a rising star in the bureau, Larry Potts, who had once worked in Boston. Morris then finally got the promotion he had been after and became assistant agent in charge of the Los Angeles office.

THEN along came Fred Wyshak. Born in Boston, Wyshak was new old blood who had returned home after a decade as a crime fighter in the rough and tumble of Brooklyn and New Jersey. He arrived at the U.S. Attorney’s Office in 1989 with a reputation as a case maker who did not suffer fools or mince words. He had no time for or patience with agents who dogged it or didn’t get it. Unlike the more typical federal prosecutor with an Ivy League background and no street sense, Wyshak had no stepping-stone jobs in mind. He just wanted to make cases—the bigger the better. Within weeks Wyshak had but one question: how come no one is doing this Bulger guy?

He had been told that Bulger was just about ungettable, that he was smart and shifty and never talked freely on the phone or dealt directly with anyone who would roll, that he had regularly outfoxed the DEA, the state police, and, most recently, the Boston police. Besides, Wyshak was told, Bulger’s not worth it. Why not check out the new Mafia boss, Cadillac Frank Salemme, the next big case?

Wyshak smiled his small smile while his skeptical eyes said, “Really?” He had seen the real Mafia in New Jersey, and Angiulo successors like Salemme seemed like penny ante bookies. In fact Wyshak was coming off a major victory in Newark, a conviction of the city’s Mafia head, a man who had so dominated the trade unions that he annually extracted millions of dollars from contractors dependent on union labor and work terms. As a prosecutor in his midthirties, Wyshak hadn’t thought twice about calling the special agent in charge of the Newark FBI office and saying, “Let’s go.”

Wyshak knew the difference between big and little fish, and as he looked over the Boston underworld, he kept coming back to Bulger. The question lingered and tantalized. Why did no one seem to care about such a natural target?

When he arrived in Boston as a thirty-seven-year-old prosecutor, Wyshak had a decade’s experience in making cases in Brooklyn and Newark by getting defendants to roll against each other. He also knew how to assemble and manage a massive racketeering case against several underworld leaders. He could do the paperwork, and he could fight in court. He learned to keep ahead of defense lawyers and developed an instinct for which defendants would fold and which would hang tough.

But while Wyshak brought his considerable playbook to town, nothing prepared him for the backstage politics of Boston. His jock mentality had a New York edge that often cut two ways. Not everybody liked him. A case maker who was always pushing a game plan, he gravitated to workers, not talkers. He disdained one agent as a “donkey stuck in mud.” In one of the first meetings with the best ally he would have in Boston—the long-suffering state police—Wyshak rubbed against one detective as “an arrogant son of a bitch, a kid from New Jersey telling us how everything works.” Yet to a small circle of friends Wyshak was a closet comedian who made lunch a riotous event with snide asides. He joked about how everybody hated him, including his own family. And when the punch was spiked at one office Christmas party and secretaries were crashing into walls, it was Wyshak taking it in with mischievous eyes.

Although Wyshak worked out elaborate strategies long in advance, his basic approach was not hard to figure out. With a heat-seeking instinct for the weak link in any criminal enterprise, he used Hobson’s choice as a weapon. Be a defendant or be a witness. Get on board or pack for prison. Robert Sheketoff, a defense lawyer who worked against Wyshak, came away respecting his tenacious intelligence but viewing him as a zealot. “I don’t understand how the government can crush a human being on the theory that if they crush enough human beings you get a greater good,” Sheketoff said. But about Wyshak’s strategy he could only grimace and say, “Hey, it’s working.”

Over the years Wyshak battled judges and defense lawyers with arms flailing, voice rising, chin jutting. In one typically stormy sidebar conference an exasperated judge once threw down his glasses on his bench and stammered at Wyshak, “You stop. You stop.”

Wyshak greeted witnesses with perfunctory goodwill and then got right to it. He once turned on an FBI agent with machine-gun intensity. “Tell us what you really think,” Wyshak demanded of the agent, who, like nearly everyone in the bureau’s Boston office, detested the prosecutor. Every time the agent began to respond, Wyshak fired another question while the judge futilely insisted, “Let him answer, let him answer.”

At first, Brian Kelly was yin to Fred Wyshak’s yang. Though Kelly did not have the experience that Wyshak brought to a big case, the young prosecutor wanted to do them badly. They shared an irreverent disregard for office politics, though Kelly had the more traditional background for the job of federal prosecutor and was an archconservative, distinctive even in a Republican shop. (An honors graduate of Dartmouth College, he was to the right of the National Review.) And unlike a lot of the career-obsessed attorneys in a competitive office, Kelly didn’t particularly care if he lost some cases as a way to learn something. But most of all, he could roll with Wyshak’s tart tongue and sharp elbows. He could even make Wyshak laugh and slow down. When others huffed off muttering, “I can’t believe he said that,” Kelly would smile and say, “Cut the shit,” or, “What makes you so smart?” Kelly had a nickname for everyone, and Wyshak was “Fredo,” just like the over-his-head brother in The Godfather.

In addition to having an even temperament, Kelly could get people to row in the same direction and was able to rebuild some of the bridges that Wyshak incinerated. After a couple of years the prosecutors became as inseparable as Bulger and Flemmi, playing off each other in and out of court. Most of all, they enjoyed the courtroom shoot-outs, and they enjoyed a challenge. They would get both in taking on Whitey Bulger.