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.
THE first obstacle Wyshak encountered as he set out on the Bulger highway was a mind-set. Many in the U.S. 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 U.S. 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 and interrogated by Wyshak, state police detective Thomas Duffy, and DEA agent Daniel Doherty. 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.
THE Wyshak posse picked up the trail that had been blazed back in the early 1980s by state police detective Charles Henderson. Henderson had overheard suburban Jewish bookies on wiretaps talking about “Whitey” and “Stevie.” As head of the Special Service Unit, Henderson had arrested all of 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.