Black Mass: The Irish Mob, the Boston FBI, and a Devil's Deal (42 page)

But Jim Ahearn didn’t care. He told the FBI director that the DEA’s conduct was “reprehensible.” He was “deeply disappointed.” His words were “in your face”: the Boston office and John Connolly were above reproach, and Whitey Bulger was the best thing ever to happen to the FBI.

It was a high-water mark in Bulger hype and FBI bravado. And once again Whitey weathered the squall in his back yard. The DEA investigation lopped off top enforcers such as John “Red” Shea and Paul “Polecat” Moore and snared scores of dealers. But no Whitey. Now it was time to coast home. Nearing retirement, Connolly wrote a report saying that Bulger and Flemmi were also thinking of calling it a day, “packing it in and going into various legitimate businesses that they own.” Flemmi, for one, was spending more than $1 million—in cash—to buy up a slew of real estate in the affluent Back Bay neighborhood.

But what Connolly considered “legitimate business” a new team of federal prosecutors would soon regard as money laundering. Despite how it seemed at decade’s end, Connolly and the gang would never have it so good again.

Some things are necessary evils, some things are more evil than necessary.

The 1989 Mafia baptism
captured by the FBI on tape seemed like a scene out of
Saturday Night Live—
as burly men took stilted oaths and burned holy cards. But it was a deadly serious event in the history of the New England mob, a last-gasp attempt by the beleaguered boss, Raymond Patriarca of Rhode Island, to bring warring Boston factions together. “Junior” was a pretender to the throne once held tightly by his deceased father, and he hoped that adding some new blood to the ranks would help calm Boston’s troubled waters. Notable Boston Mafia malcontents Vinnie Ferrara and J. R. Russo were there, nodding and smiling. Leaving the show of unity, Ferrara said, “Only the ghost knows what really took place over here today, by God.”

Not quite. Whitey Bulger was rubbing his hands on the sidelines, gleefully aware that another Mafia cadre was about to bite the dust by putting racketeering evidence on tape for the feds. Once again top mafiosi would soon face the music played in court and have little choice but to plead guilty to long terms. Patriarca, with the lightest criminal record, was sentenced to eight years; Russo got sixteen years; and Ferrara was dealt the stiffest sentence of all—twenty-two years. Once again Whitey and Stevie had helped target their enemies and then got out of the way.

The shattered mobster hierarchy also paved the way to the top for Stevie’s old partner from the 1960s, Cadillac Frank Salemme. Just out of jail, Salemme was planning a rapid ascension. He revived a loose alliance with Flemmi, a reunion of their two-man death squad of the late 1960s when they carried out hits for Larry Zannino. Salemme would soon manage to survive a clumsy assassination attempt against him outside a pancake house, for which he blamed Ferrara. But the gunfire did not slow his ambitious program to take over the Mafia and ally himself with Flemmi and Bulger.

The law enforcement terrain began to shift as well. For starters, John Connolly stepped down at the end of 1990. He was feted by his colleagues at a raucous party before making a soft landing as head of corporate security at Boston Edison, a company that had long curried favor with Senate President William Bulger. Around the same time, Connolly moved into a condo building in South Boston that had adjoining units belonging to Kevin Weeks and Whitey Bulger. Connolly quickly moved up the corporate ladder to the job of in-house lobbyist and an executive salary of about $120,000. From a Prudential Tower office above Boston’s Back Bay, Connolly worked with legislators at Bulger’s state house and did some Washington lobbying for the utility. But his interests stayed parochial. His office wall, decked out with photos of local politicians and sports figures, had a special place for Ted Williams, his boyhood icon.

Without Connolly in place, Bulger began to scale back and focused on South Boston holdings rather than looking for new business. He even forged a uniquely Whitey Bulger retirement plan: he “won” the state lottery. After a winning ticket was sold at his Rotary Variety Store, Bulger informed the $14.3 million jackpot winner that it would be in his best interests to acquire a new partner. Whitey and two allies left the customer half of the proceeds. Bulger claimed about $89,000 a year in after-tax income for himself—a stipend that could support his lifestyle against audits by the increasingly snoopy IRS. Investigators later found that Bulger paid the ticket holder $700,000 in dirty money to get an official cut worth $1.8 million over the next twenty years.

For his part, Flemmi launched his 401k plan with real estate trusts he controlled through relatives and in-laws. The 1990s marked his whole-hog immersion in Boston’s toniest neighborhood, the onetime Brahmin bastion of Back Bay. In 1992 he sunk $1.5 million in cash into a six-unit condominium building and two smaller units and some residential property in surrounding suburbs.

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.

Both Wyshak and Kelly had instinctively rejected the unspoken view that the FBI was the best client in the office. Both had worked in U.S. Attorney’s Offices where prosecutors worked with agents from several federal and state agencies, not just the FBI. And it fit with Wyshak’s mantra. No screwing around. Try the cases. Win some. Lose some.

After a while another prosecutor, James Herbert, joined the Wyshak-Kelly team, arriving as the best writer in the office. Like his writing, he was orderly, clear-minded, and to the point. Not as madcap as his new colleagues, Herbert was a levelheaded scrivener making his way around the courtroom. He had an Ivy League résumé more typical of the office’s lawyers, the kind that ran three pages to Wyshak’s four paragraphs.