Black Mass: Whitey Bulger, the FBI, and a Devil's Deal by Lehr, Dick, O'Neill, Gerard (2012)

PART THREE

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

JOHN LE CARRÉ,
THE RUSSIA HOUSE

CHAPTER SEVENTEEN

Fred Wyshak

The 1989 Mafia baptism the FBI captured 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 his deceased father once held tightly, 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. His colleagues feted him at a raucous party before he made 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 with 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.

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.

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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 US 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 although 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 shootouts, 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 US 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.

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The first obstacle Wyshak encountered as he set out on the Bulger highway was a mind-set. Many in the US Attorney’s Office wanted to stay religiously focused on the Mafia and follow the FBI’s lead, a long gray line headed for a decade by Jeremiah O’Sullivan and then, in his wake, by assistant US attorneys Diane Kottmyer and Jeffrey Auerhahn. (The pro-FBI contingent was led by Jim Ring and Kottmyer, a competent assistant in the Angiulo case and a dour O’Sullivan disciple addicted to the FBI.) Wyshak’s early effort to target Bulger was never opposed directly. The response was never, “That won’t work.” It was, “Interesting. Let’s talk more.”

Then Howie Winter strayed onto the playing field. By the end of 1989 Howie had been out of jail for a few years and was living in exile in rural Massachusetts, working at a garage and staying out of Boston while he was on parole. Winter had fallen on hard times and was collecting workmen’s compensation from a garage injury. But the lure of the kind of easy money he had made in the 1970s proved irresistible, and soon enough the state police and the DEA got a tip that Howie was moving cocaine. The detectives took the case to Wyshak, the outsider with no history or agenda and no ties to the FBI. Wyshak immediately formulated one of his game plans: an aging and wired Howie talking to Whitey about “Santa Claus.”

But they had to catch Howie first. The snitch network reported that Howie was foolishly taking some orders over the telephone. After sufficient “probable cause” detective work, Wyshak obtained court authority to do a wiretap on Winter’s phone and then held a meeting among federal and state investigators to go over “minimization” rules for investigators listening in on the calls.

The bug was compromised the first day it went up. All investigators had was Howie goofing around on the phone. An informant told them that Howie warned him away from telephone contact. It was a fast education for Wyshak in the ways of Boston law enforcement.

Wyshak had gone about the Winter investigation the way he did in Brooklyn—setting a course of action with several agencies in on the details. In New York it had been possible to collaborate over a cross-section of investigators. But not in Boston. So Wyshak was forced to adopt the prevailing need-to-know strategy. After putting out word that the Howie case was kaput, he began working in earnest on a new plan with a chosen few. Using what a colleague calls “great instincts,” he zeroed in on one of Winter’s cocaine suppliers as someone who would roll. The supplier was a fortysomething ex-convict who had just started a new family and had a wife and baby at home. The investigators built a cocaine trafficking case against him, then gave him the choice: doing heavy prison time or coming on board with prosecutors and staying home with the new family. The dealer was wearing a wire within a year, talking to Howie about distributing kilos of cocaine. In 1992 Howie was arrested as he attempted to sell coke. In a flash, Howie was looking at a minimum of ten more years in prison and as many as thirty if Wyshak could convince a judge that his earlier convictions for race fixing and extortion made him a career criminal.

Howie was taken to a motel, where Wyshak, state police Detective Thomas Duffy, and DEA Agent Daniel Doherty interrogated him. As if Winter didn’t know, they explained his predicament. He was told: we’re really after Whitey Bulger, who, by the way, hasn’t done you any recent favors. Can we work something out here? Howie listened hard and watched the question hang in the air. He asked to speak to his wife, Ellen Brogna, about it. “Become a rat?” she asked him in horror. “You should tell them to go fuck themselves.” So that’s what Howie did.

In May 1993 Winter pleaded guilty and was sentenced to ten years. Once king of Winter Hill, he left court dressed in a drab gray suit on a drab gray day, a sixty-two-year-old gangster looking at a decade in prison, carrying all his belongings in a brown paper bag. A convicted drug dealer with a strong wife—but no rat.

Wyshak had bagged a big target in Howie even if it didn’t get him to Whitey. And the plea bargain meant much more than one more Winter Hill figure behind bars; it forged a lasting alliance between the high-energy prosecutor and the state police detectives and DEA agents who were aching for another shot at Bulger. For his part, Wyshak just wanted to make cases. So they saddled up.

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The Wyshak posse picked up the trail that state police Detective Charles Henderson had blazed back in the early 1980s. Henderson had overheard suburban Jewish bookies on wiretaps talking about “Whitey” and “Stevie.” As head of the Special Service Unit, Henderson had arrested all the bookies at one time or another and now knew they were paying rent to Bulger. Whitey annoyed the combative detective on a personal level. He also realized Bulger was getting a pass on his extortion, that no one else in law enforcement gave a rat’s ass about it except the state police and a few local prosecutors. (In fact, the FBI had a formal policy of not stooping to chase lowly bookies.)

But Henderson saw the bookies as a bridge to Bulger and knew that they would be vulnerable to a concerted assault—if one could ever be mounted. Henderson knew well the bitter legacy of the Lancaster Street garage and even something about the Halloran murder aftershocks. But most of all he was a visceral cop who decided he’d had enough of this bully who swaggered out of South Boston on a pass from the FBI. Henderson did some long-range planning. He needed bookie cases that would enable police to take control of gambling profits by using forfeiture statutes. It was a sure way to get a bookmaker’s full attention. And he needed to hand the bookies over to federal prosecutors like Wyshak as witnesses against Bulger for some kind of racketeering case. As he began plotting his way at the end of the 1980s, he realized that politics was at least as important as evidence.

By 1990 Henderson saw that the timing was finally right. He had just been promoted to head of the uniformed state police. And there was a new lineup at the top of law enforcement that could work together. The new state attorney general, Scott Harshbarger, the new district attorney in Middlesex County, Thomas Reilly, and US Attorney Wayne Budd were friends who could work together. One factor plaguing earlier efforts against bookies and organized crime had been the fragmented jurisdictions of county district attorneys. It made it hard to chase bookies with phone taps across county lines. So one of the first moves Henderson made in his new job was to have Harshbarger’s office obtain blanket court authority to chase bookies across county lines. His second was to appoint his protégé, Thomas Foley, as head of the Special Service Unit.

The plan was to make cases against bookies that could be handed off to the feds, who could use their tougher sentences to turn bookmakers, accustomed to paying $3,000 fines in state court and never going to jail, into witnesses. The middle-class bookies were more businessmen than archcriminals, and there were not many who would stand up to ten years in a federal prison.

The effort got under way in Middlesex County, chosen because of its heavy betting (it was the state’s most populous county) and because the state police worked well with Reilly, who had been a longtime prosecutor there. Phone taps went up in 1991 and multiplied quickly as one bookie led investigators to another. There soon was an embarrassment of riches, and the state police had to make a fast decision: whether to chase both Bulger’s gang and Mafia bookies. In some fancy footwork the investigators slyly handed off Mafia bookie “Fat Vinny” Roberto to the FBI but quietly retained control of Chico Krantz and his crew of Jewish bookies paying Bulger.

Although Roberto eventually fizzled, state investigators made dramatic progress with Chico, especially when a search warrant uncovered the keys to Chico’s cash box. Krantz played it cozy, but the idea that he could stay out of jail and get some of his money back if he did a little talking intrigued him. Whitey was where things bogged down.

Foley was ideally suited for carrying out the next step in the delicate mission. Having worked on special assignment since 1984 with the US Attorney’s Office and the FBI, he knew how to ease the case to federal prosecutors who wouldn’t just turn things over to the FBI for more legwork. Foley took his pitch and Chico’s predicament down the hall to Fred Wyshak. Foley convinced him that a criminal merger had taken place and power had shifted to Bulger’s gang. Wyshak was so impressed that he didn’t even make a wisecrack.

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Bringing in skittish bookies looking for a deal to stay out of jail was one thing; slipping under Bulger’s stranglehold on drug dealing in South Boston was quite another. Throughout the 1980s Southie had been an impregnable fortress, but now a crack began to show.

Timothy Connolly was a mortgage broker trying to outrun his roots as a South Boston tavern owner. He had a simple story of extortion to tell about Bulger putting a knife to his throat for money. But the US Attorney’s Office tried to turn Tim Connolly’s solid single into a home run. They constructed an elaborate plan to infiltrate Bulger’s financial operation, a doomed effort that fell far short of the mark. Just as some in the FBI would have liked, Timothy Connolly was forgotten—almost.

Four years later, in 1994, Brian Kelly bumped into an investigator in a courthouse corridor. “Don’t forget the Tim Connolly stuff,” the investigator said. “It’s good.” Kelly looked at him blankly. Tim Connolly? Tell me about him, Kelly asked.

It had all started, the investigator recalled, in 1989. A car almost cut Tim Connolly off as he walked along a South Boston sidewalk on a simmering summer day. It screeched up the curb, and Connolly squinted into the sun to see inside. With a rush of adrenaline, he saw Whitey Bulger and Stevie Flemmi glaring out at him. The driver barked to meet Bulger at the Rotary Variety Store and sped away.

Tim Connolly was flummoxed. What’s this? he thought with a gnarled stomach. He got an emphatic answer the second he made his way into the dark storage room in the back of the variety store. “You fucker,” Bulger screamed at him, pulling a knife from a sheath strapped to his leg. Bulger began viciously stabbing empty cardboard boxes stacked against the wall.

Tim Connolly’s hanging offense was that he had taken too much time in arranging financing for someone who owed Bulger money from a busted drug deal. Tim Connolly had simply not moved fast enough.

Holding the knife against Connolly’s throat as Flemmi watched the door, Bulger slowly simmered down. As with similar tirades, Bulger’s fury seemed calculated, another episode in the Bulger production called “A Second Chance.” “I’m going to let you buy your life,” he said. It was the classic Bulger scenario and price all over again—$50,000 and how-you-get-it-is-your-problem. Once again a terrified victim was thankful to be paying Whitey for not killing him.

Tim Connolly pleaded for some time and said he had to go to Florida in the next few days. Bulger set the terms: twenty-five large before he went, and twenty-five on his return. Tim Connolly borrowed $25,000 and brought it in a paper bag to the store. As he left, an appeased Bulger told him, “You are now our friend.”

When Tim Connolly returned from Florida, he took $10,000 more to the store. But Bulger had no time for him now and motioned him to his associate, Kevin Weeks. After taking the money, Weeks looked up and said, “Where’s the rest?” Coming, Connolly said wearily. Coming.

But in fact Tim Connolly was going. Desperate to get away from a killer debt, he began talking with a lawyer who could get him to federal prosecutors. Like Brian Halloran, he was looking for a safe haven. But the bloody history showed that nothing involving Whitey Bulger was simple or easy.

Within a matter of weeks Tim Connolly was swept up again, this time on the other side of the line. The DEA and Boston Police were wrapping up their investigation into South Boston, and Tim Connolly was subpoenaed to talk about a second mortgage he arranged for one of Bulger’s dealers.

Using phone taps and shoe leather, detectives had worked their way up from a street dealer to the highest level in Bulger’s cocaine network. The evidence included taps on the phone of a dealer who had lost money in a deal involving Bulger—the same dealer who got Tim Connolly summoned to the variety store. The detectives knew nothing of the threat to Tim Connolly but wanted to find out if he was financing drug deals through his banking connections. What the local police also didn’t know was that Tim Connolly was already dealing with the FBI after making his way to the US Attorney’s Office.

But as always seemed to happen when events veered dangerously close to Bulger, there was a derailment in federal offices. One of the top prosecutors in the US Attorney’s Office, A. John Pappalardo, decided to use Tim Connolly to get into Bulger’s finances. He turned Tim Connolly over to two handpicked FBI agents who had no ties to John Connolly. They wired the mortgage broker as a way to get an inside look at Bulger’s money laundering. But then Whitey Bulger suddenly stopped dealing with Tim Connolly.

In the end Tim Connolly was not used in the DEA and Boston Police case against Bulger Drug Network because they never knew about the extortion in the back room. And the FBI’s attempt to use Tim Connolly on Bulger’s money laundering never got off the ground. But if investigators and even some prosecutors never knew Tim Connolly’s value when it counted the most, the same cannot be said of Whitey Bulger. He knew all about the threat that Tim Connolly posed, almost immediately after the FBI had him wired.

Stevie Flemmi said that after Tim Connolly was sent to the FBI, “Mr. Bulger told me that Tim Connolly was wired up and that he was directing [at] us as a target … the information came from the FBI.” Flemmi was quite certain the tipoff came from John Connolly.

Kelly took all of this in. It was a lesson in how hard it would be to bring a case—any case—against Bulger. But it was also a reminder that perhaps—just perhaps—it could be done.