Betrayal: Whitey Bulger and the FBI Agent Who Fought to Bring Him Down

by Robert Fitzpatrick

  There it was. After all the years of frustration and betrayal, I’d finally gone public about what I knew and had experienced, and for the first time I didn’t feel I was abandoning or reneging on the oath I’d taken as an agent. The only way the FBI could be fixed was to first acknowledge it was broken. Nothing I’d tried up to that point had worked, and more lives continued to be ruined or lost. By remaining silent I was essentially condoning that behavior. It wasn’t about getting even; if it had been, I’d have gone to the Globe the day I resigned and packed up my desk in Providence. I’d thought, hoped anyway, consenting to the interview might excise the demons of that period that had destroyed my dream. Instead, rehashing the whole sordid experience only made things worse, and I realized it didn’t mark the end of my war, only the beginning.

  It started to rain while we were on the beach, so Lehr and I went back to my house. I remained both tense and pissed, since I had just relived the darkest period of my life in chronicling why I’d left the Bureau. It all seemed so clear-cut when articulated in succinct fashion, though not to the FBI. Couldn’t they see the corruption? Couldn’t they see that they had been taken over by a thug, a sniveling rat? To the Irish a tout is a tout, and Bulger was a tout! I told Lehr I had worked multiple informants throughout my career in equally high-profile cases, so I knew what I was talking about. I had taught at the FBI Academy about these very informant problems and had been a profiler of people and events that spawned such debacles.

  I told Lehr about what Morris had said, “You’ll never close Bulger.” I was Irish, but not Boston-Irish. I didn’t know the inner city, but my childhood experiences in the Mount made me understand the culture and mores of Boston’s Irish Southie. When I started encountering Bulger and Connolly, I was quick to find out what made them tick. And yet the same pro-Bulger proponents continued to prevail. I had spent the formative years of my youth watching my back at the Mount and, thanks to Bulger and his Bureau cronies, I spent what should have been the peak of my professional life doing the same thing.

  “The FBI is being compromised. That’s what pisses the shit out of me. I mean the FBI is being used,” I told Lehr.

  Just as we were used as kids in the Mount, held hostage by bullies and counselors, forced to fend for ourselves as we carved out a reasonable degree of security that often extended no further than our bunks. The Mount as metaphor for Boston was especially fitting, given that the entire city was being harmed by the drugs and violence pushed by Bulger and the corruption that fed his empire. You just couldn’t escape it. If it wasn’t Whitey operating in the city’s seedy underbelly, it was his brother Billy ripping off the city and state from his office in the State House. The Brothers Bulger, Howie Carr’s brilliant and powerful study of the era, is subtitled How They Terrorized and Corrupted Boston for a Quarter Century for a very good reason.

  I went on to tell the Globe’s Dick Lehr that the root of the problem came down to what I had taught at the FBI Academy. The most basic seduction facing any FBI informant handler was “overidentification.” In other words, letting the informant run the agent instead of vice versa. To put it another way, Connolly and Morris had “gone native” with Whitey Bulger just as Rico and Condon had years before with Joseph Barboza. What was clear to me, and I hoped to Lehr, was that Bulger and other informants like Barboza had dragged the FBI’s name and reputation through the mud. And, for trying to get the Bureau straight again, my name had ended up shit-canned by the very people who should’ve joined my efforts instead of fighting them tooth and nail. If this were the Mount, I’d still be hanging from the steam pipes.

  The rain was still falling when Dick Lehr left my home, his windshield wipers fighting to slap it away as he drove off. I wondered what he’d do with what I’d given him and what he’d been able to glean elsewhere. Would the FBI squash his story somehow? Would power be exerted over his superiors at the Globe and its owners? After what had happened to me, anything seemed possible.

  Two months later, on September 19, 1988, the Boston Globe published the first installment of Lehr’s explosive Spotlight Series. The articles, which ran for four days, tore the lid off the whole unspeakable mess by encapsulating Bulger’s hold on the FBI and how that derailed the attempts of locals cops, Staties, and drug agents to put him away once and for all. The evidence and will to nail Bulger had always been there, forestalled by the Bureau at every juncture.

  The Globe series marked the first public exposure and rebuke of the FBI’s handling of the Bulger fiasco. Mention of Angiulo, who’d been taken down by my squad, formed another ironic counterpoint, since that was what Whitey had been enlisted to help with but he instead ended up accomplishing nothing that didn’t serve his own ends. The Globe series went on to describe, in fairly amorphous terms, the DEA’s attempt to get Bulger via federal wiretaps (thanks in large part to intelligence furnished by John McIntyre before he “disappeared”). To no avail, of course, since Connolly, Morris, and probably others made sure Whitey knew his car and condo were all bugged.

  In fact, as the Globe article from September 20, 1988, alluded, those in the DEA involved in the 1984 Bulger investigation had determined they couldn’t even share their intentions or information with the FBI. As anyone in law enforcement knows, this represents an egregious break from established procedure and protocol, and the DEA would only have opted for it had they determined no other viable option existed. It seemed to me they’d come to the same conclusion I had long before: that the FBI had absolutely no intention or desire to deal with Whitey Bulger as a problem or even recognize that he posed one.

  If I’d had any questions about Lehr’s intentions or veracity in our walk on the beach, his Spotlight Series written in tandem with Gerard O’Neill and Christine Chinlund pretty much vanquished them. The series of articles chronicling the rise to power of Whitey and Billy Bulger finally dug deep enough below the surface to find the same mess I’d found eight years before when I arrived in Boston, and their reporting gave my own accusations a fair and thorough hearing.

  “Part Three,” for example, covered a portion of the FBI’s complicity in helping to fuel Bulger’s rise to power. (The series also expertly paralleled Whitey’s pursuits with those of his powerful pol brother Billy, especially fitting since my investigation of at least one of the scandals involving Billy was derailed by my departure from Boston.) It was the beginning of the end for Whitey Bulger and his enablers, but, even then, the end would not come soon enough. The new Boston SAC, James Ahearn, would publicly defend the FBI position by flatly denying Bulger and Flemmi’s informant status instead of the usual “no comment.”

  The Spotlight Series wasn’t afraid to name names either, and did a commendable job of tying the disparate strands together, while suggesting some of the twisted connections that seemed too incredible to believe. It even revisited the 1979 Race Fix case that cemented Jeremiah O’Sullivan’s complicity in the Bulger debacle and that remains to this day one of the clearest shots the Bureau had to get Whitey, although they failed to act.

  The Race Fix case had sent several Winter Hill Gang members to federal prison. One of these, Anthony “Fat Tony” Ciulla, was unequivocal in his insistence that Whitey Bulger and his right-hand man Stephen Flemmi had taken a hefty cut of the profits. But the ever-crusty Jeremiah O’Sullivan, who saw his position as head of the Strike Force as a stepping-stone to a lucrative career as a high-profile defense attorney, which he went on to pursue in the 1990s, still refused to indict the two men who were the operation’s kingpins.

  “We had no evidence against them outside of Ciulla’s word,” he told the Globe reporters. “Very rarely do you indict on just the word of an informant.”

  25

  BOSTON, 1995

  “Did you hear about Bulger?” one of my old squad members asked over the phone in early 1995.

  “What’s he done now?”

  “He’s gone.”

  “Guess he got one last tip,” was all I could think to say, a better prophet than I’
d ever imagined, as it turned out.

  I suppose I knew this day would come, the only conceivable resolution given the FBI clearly had no intention of ever prosecuting Whitey. I remember feeling strangely ambivalent at first, taking the news in stride. On the one hand, Bulger’s disappearance dredged up all the painful memories about my failed attempts to close him. On the other, the fact that he had been allowed to slip away was final affirmation of the Bureau’s utter incompetence and malfeasance in their dealings with him. This while providing no vindication for my efforts or claims at all, and only reviving my bitterness.

  That wasn’t all. The fact that Bulger was now on the lam presented a very real threat to me. He’d already made his intentions plain to John Morris, and the fact that he was now free to come after me, and my family, unsettled my wife Jane and our two young daughters, who were afraid to go to sleep, to school, or leave the house at all. Our friends offered us safe harbor, a place to hide from a man they knew wanted vengeance against me for pursuing him without end. Bulger had killed plenty for just talking about him, telling the truth, and I’d continued to do just that in my years after leaving the Bureau. The tension was palpable, increasing with each call from friends or associates to check on my well-being. I was never far removed from my gun and made sure the blinds were always drawn over the windows. Seeing the fear in the faces of my wife and daughters replaced my anxiety with anger over the fact that their lives were being disrupted by this psychopath who should have been jailed long before he had the opportunity to escape. I almost wish Bulger had come after me, so I could have settled things once and for all myself.

  Bulger’s disappearance became a de facto demarcation point whereby the debacle, as far as I was concerned, moved the action from the street almost entirely into the courtroom. John Connolly, who would soon face trial and imprisonment for his actions, had retired from the Bureau. John Morris would suffer a heart attack while in Quantico following a telephone call from Whitey apocryphally telling him “he was going down with the ship,” a threat to effectively end his career as well. And not long after Whitey vanished, hearings before Judge Mark Wolf in Boston federal court would further expose much of the way the FBI had done business in Boston over the years.

  The playbook had already begun to change with Connolly’s retirement as 1990 drew to a close. It’d be easy to say he saw the writing on the wall, but the writing had been there for years, Connolly brash and arrogant enough to ignore it. Still, he saw an opportunity to get out while the getting was good. I heard a hell of retirement party was held for him; guess my invitation got lost in the mail. Whitey’s, too. Connolly’s loyal service to one Bulger, though, had earned him payback from another Bulger. Among the “perks” of his retirement package was a “lobbying job” for Boston Edison, a power company, at Billy Bulger’s State House complete with a $112,000 annual salary.

  “We take care of our own here,” Billy had told me during our one meeting, as much a show of force as a warning.

  And he had taken care of John Connolly splendidly. Connolly had paid his dues to the Bulger family and was now reaping the rewards. John Morris left Boston soon after, bound for Los Angeles to become Assistant Special Agent in Charge there, en route to his heart attack a few years later. I’d like to say I smiled over the irony of Morris assuming the same position in L.A. I’d held in Boston, but I didn’t.

  As for Whitey, years prior to his disappearance he hit the lottery on someone else’s ticket. The jackpot number had been purchased at the Rotary Variety Store Bulger owned, and he was able to “cajole” the winner into splitting the proceeds fifty-fifty with him. That amounted to about $90,000 a year after taxes, enough to live pretty well on if it ever came to that.

  But this time even Whitey must have seen the writing on the wall, especially with the security blanket he’d maintained, in the form of Connolly and Morris, gone. Not that he intended to lay low, not with the Boston rackets and a drug trade under his control. The new mafia boss, Frank “Cadillac” Salemme, may not have taken his orders directly from Bulger, but neither did he make any move that would have stoked the old tribal fires between Boston’s Irish and Italian mobs. The only kind of peace Whitey knew was one that left him calling the shots, and Salemme was happy to cede whatever it took to keep that peace. Since he’d have far less insulation to cushion him the next time his escapades resulted in blowback, Whitey was more than happy to let Salemme take the heat while he laid low, at least in relative terms.

  Then a new “sheriff” came to town, specifically an assistant in the U.S. Attorney’s Office by the name of Fred Wyshak. The New York–born Wyshak had the advantage of a proven background, like mine, having successfully prosecuted the New Jersey mob in his last stopover. He didn’t have to worry about John Connolly, John Morris, or James Greenleaf running interference for the murderous Bulger. Nor was he beholden to the legacy and rules of the FBI that had so hamstrung my efforts.

  Brian Kelly, a thirty-year-old U.S. attorney who worked the case with Wyshak, couldn’t believe the evidence before them, specifically that a pair of psychopaths, Bulger and Flemmi, had been able to run roughshod over one of the largest Bureau offices in the country. To Kelly and Wyshak himself, this was absolutely mind-boggling and further complicated by the fact that they couldn’t find a single example over the past decade where information provided by the prized Bulger had led to an arrest, much less successful prosecution.

  Fred Wyshak, who I met only briefly and with whom I had very little real interaction, didn’t have to worry about embarrassing the Bureau. He had the entire United States government behind him and was smart enough to first target Howie Winter, recently released from a long stretch of prison. His Winter Hill Gang had been remade in Whitey Bulger’s image. Operating out of Southie as a satellite of the Sommerville Winter Hill Gang, it was similar in a way to the North End as an organized crime satellite to Patriarca’s OC Providence gang. It allowed Bulger to pull the wool over Winter’s eyes because no one knew what was going on “down there” in Southie.

  Howie Winter later remarked that Bulger built his power base that way, and Winter had no choice but to accept it: there was plenty of work to go around, some of which made him fodder for Wyshak on a drug beef. What’s clear from this arrest was that Wyshak’s focus was trained on Bulger. And when Winter refused to give Whitey up, clinging to an old code his Winter Hill rival had long abandoned, Wyshak resolved to find another way to get his true quarry.

  That is, until the new assistant U.S. attorney fell victim to the culture of corruption that still pervaded the Boston office of the FBI, even with the recent departures of John Connolly and John Morris and less recent transfer of James Greenleaf. Wyshak wired up a Bulger money launderer named Tim Connolly (no relation to John) to get the dirt he needed, only to have Whitey suddenly clam up around Connolly. Stephen Flemmi would later testify that Whitey had been tipped off, the tradition seemingly having outlived its founders.

  Still, Wyshak didn’t give up. He set his sights on what he saw as the weak link of Bulger’s operation—bookmaking—to make a federal racketeering case against him. With his FBI family and Jeremiah O’Sullivan no longer there to short circuit such efforts, Whitey found himself suddenly vulnerable. The man wearing the bull’s-eye instead of the one painting it on others. Wyshak went after Bulger’s army of bookies like a pit bull, ultimately accumulating enough evidence to secure racketeering indictments against Salemme, Flemmi, and Whitey himself in late 1994. Flemmi was taken into custody, Salemme fled to Florida where he, too, was arrested a few months later, but Whitey was nowhere to be found. Whether he was tipped off or not in one last show of deference by the Bureau, at least to some, remains in dispute. What isn’t in dispute is that his gangster associate Kevin Weeks funneled enough money to Whitey early on to keep him on the lam through America’s underbelly. Places he wouldn’t have been caught dead in before, where his status as a legendary kingpin on the streets of Boston meant nothing.

  The next contact
anyone else had with Whitey was none other than John Morris in that phone call while Morris was serving as training director at the FBI Academy. There are differing versions of that conversation, but one thing is clear in all of them: Whitey warned Morris not to talk, not to give him up. Do that and Morris would be going down, too. Or worse. Bulger disappeared for good after that call and, other than a few rumored sightings, wasn’t heard from again until his June 2011 capture in Santa Monica, California.

  But his name surfaced plenty in the now infamous Wolf hearings that began three years after his disappearance. Infamous because the mob-related testimony and evidentiary material blew the lid off the FBI’s casual use, and protection, of criminals as informants, and nearly blew up the case against Frank Salemme and the other defendants.

  “The court has reviewed the defendant’s Motion to Disclose Confidential Information and Suppress Electronic Surveillance conducted in this case,” wrote the presiding judge, Mark Wolf, in one of his rulings after several days of closed sessions. “In this case, in which the defendants are charged, among other things with conducting a racketeering enterprise, the fact that a codefendant was during the relevant period a confidential informant for the FBI would, if true, constitute exculpatory information to which his codefendants are entitled.”

  In other words, the State, and thus the FBI, had no choice but to reveal who their informants were and how exactly they had been used. What many had suspected for decades, starting with Colonel John O’Donovan of the Massachusetts State Police, the very root of the cancer that had infected the Boston office, was about to be laid bare for public inspection in open court. And that would mean, under no uncertain terms, many of the claims that had followed my interview with Whitey Bulger that night in his Quincy condo, and subsequent recommendations that he be closed as an informant, were going to be revealed. Specifically, that he had played the FBI for years without furnishing the exacting information that supposedly made him indispensable.