Betrayal: Whitey Bulger and the FBI Agent Who Fought to Bring Him Down (6 page)

BOSTON, 1981

In preparation for my meeting Bulger, and making my decision as to his fate as an informant, I set out to research as much as I could, assimilating the facts from file reviews and relying on previous experience and knowledge of the players involved. I drew off my Miami supervisory experience in ABSCAM, which taught me that file reports were important, but they don’t tell the complete story, especially when trying to determine what’s really going on in a man’s head.

They say a man is the sum of his deeds. Well, I started out by trying to learn everything I could about James “Whitey” Bulger’s deeds. I already knew he grew up in Southie, an Irish enclave just outside of Boston proper. Bulger’s home of Southie had been a hotbed for criminal activity long before he was born, making it an easy road to take. His brother Billy took a theoretically more civil road known as politics, following in the footsteps of congressmen like John William McCormack and Joe Moakley, to become president of the Masschusetts State Senate at the statehouse in Boston.

Whitey followed the gangster route and in 1956 was convicted of bank robbery. By 1975, when he was reopened as an informant by John Connolly shortly after Connolly’s transfer from the New York office, he had served nine years in various penitentiaries, including Alcatraz and Leavenworth. He had a reputation in Southie for being a nice kid, a kid who helped the elderly, the kind of kid who worked with the church in handing out turkeys on Thanksgiving and Christmas holy days.

Connolly liked to tell the “ice cream” story about how Whitey befriended him at the time the future FBI agent was being taunted by bullies in Southie. Whitey bought the younger, fearful boy an ice cream cone and sat down with him on nearby stoop.

“Those punks ain’t gonna bother you no more.”

Connolly looked up from the ice cream dribbling down the side of the cone.

“I’m gonna have a talk with them,” Whitey continued. “You got nothing to be scared of.”

From that point on, Connolly could hardly be objective in his dealings with Bulger. I suppose he viewed the expensive diamond ring Bulger would give him years later as no different from the ice cream cone.

What’s missing from Connolly’s heartwarming ice cream story is that Whitey was in reality the biggest bully in Southie, actually in all of Boston for that matter. Over the years, and despite Connolly’s sentimental view of him, Whitey had built a well-earned reputation as a stone-cold killer. He’d proven himself a brutally effective enforcer against the muffs who welched on their bets, as well as a part-time hit man for Raymond Patriarca, the head of the New England mob. Far from the saintly protector Connolly idealized, there was no arguing that Bulger was more comfortable with a gun in his hand than an ice cream cone. For years, the Massachusetts State Police, Boston Police Department, and Drug Enforcement Agency had Bulger lined up in their investigative crosshairs, only to have their efforts rebuked by Bureau interests committed to Whitey’s protection at all costs.

In preparation for assessing Bulger firsthand, I reviewed his FBI in-house files and materials. Morris and Connolly talked him up as a “great guy” who, more important, had provided a great deal of evidence about the mafia and drugs. Yet the “evidence” they boasted about was nowhere to be found in any of the files, just as Agents Knotts, Cronin, and Crawford had told me.

Morris emphasized the fact that Bulger did not drink, he did not do dope, and, in fact, had it in for the dopers in his territory around Boston, especially Southie. They painted a picture of Bulger as a veritable Robin Hood who distributed turkeys over the holidays to the poor and elderly just like he gave an ice cream cone to a bullied young boy years before.

“You’ll like Jim,” Morris and Connolly kept telling me, never referring to him by his more accepted nickname.

Connolly boasted that Bulger was a “great friend” of the FBI who never accepted money for his informant work, providing his services for the love of his country instead. Morris seconded Connolly’s benevolent description of Bulger as a guy I would not only like, but “love.” Morris, it seemed, had the unenviable job of cleaning up Connolly’s crap on paper. And both looked at the string of accolades coming their way from FBIHQ as a license to handle Bulger and Flemmi any way they chose, even if that entailed letting them “get away with petty crimes and such.”

Connolly understood that his informants had the right to continue their gambling operation and loan-sharking business and even to collect rent from bookmakers as long as there was no violence. His attitude was one of “don’t ask, don’t tell.” If the FBI had no direct corroboration from its own independent sources, then the office effectively knew nothing because Connolly didn’t want them to know anything.

The great paradox here was that Connolly was a self-proclaimed loyal agent who idolized and idealized the FBI in every way. In ironic counterpoint, he had that diamond ring Bulger had given him engraved with the motto of the Bureau: Fidelity, Bravery, and Integrity. I would later learn that the ring was stolen property. If the suspicions of Colonel O’Donovan and others were correct, Connolly had already provided Bulger plenty in return, in clear violation of the FBI’s
Manual of Investigative Operations and Guidelines.
That manual clearly states that agents are “to insure that [informants] are not provided any information other than that necessary to carry out their assignment.” The manual might have been vague about what crimes were permissible for informants, but made very clear the informant could not be a murderer or the head of a criminal enterprise. The head of a gang, like the Winter Hill organization, then, should have expressly been off limits.

Early one evening in late March of 1981, Morris drove me to Whitey’s condo in Quincy; it stood amidst a neat row of others just like it, plain vanilla and innocuous. Along the way he regaled me with story after story of his own experiences with the gangster, finishing each story with, “You’re gonna like this guy.”

I asked Morris about Whitey being described as the head of the Winter Hill Gang.

“Howie Winter is in jail,” he told me. “So it’s just a temporary appointment.”

“For how long?”

“Don’t know.”

“As long as Winter is in?”

“Could be.”

“That’s a long time.”

Morris seemed to have no problem with the fact that Bulger, as an FBI informant, was the acting head of an organized crime gang. After all, Morris was the “pencil” who could write up the reports in a way that convinced his superiors that Whitey was at the time the best informant to get the Bureau what it wanted. Everything else he covered was vague, noncommittal, and even muddled. I knew about informants; I had run enough of them myself in high-profile cases to know when the tail was wagging the dog.

In 1967, I was on special assignment in Mississipi from Memphis, where I’d been assigned after beginning my Bureau career in New Orleans two years earlier. I was charged with infiltrating the Ku Klux Klan and trying to develop informants. There had been a rash of murders down there, including hanging and shooting blacks and bombing synagogues.

My job was to get probable cause and evidence on Sam Bowers, the head of the White Knights of the Ku Klux Klan of Mississippi (WKKKKOM) and the perpetrator behind all the violence. There were klaverns, the Klan clubs, in my area around Hattiesburg and Laurel where I played the undercover role of a New Yorker going to school in Jackson. I would act naïve around people, especially those I suspected of being Klan sympathizers, in no small part because these “kluckers,” as we called them, were fundamentally proselytizers.

I’d always choose a propitious moment to reveal my true identity and attempt to develop an individual as an informant who could penetrate the klavern in question. The key was knowing how to identify kluckers or members of the WKKKKOM. Distinguishing the wannabes or would-bes from the true players being the trick.

The first person I tried to turn was anything but a wannabe. Joe Danny Hawkins turned out to be the head of the klavern in Jackson, as well as an avowed hater of law enforcement. Nothing I could say or do was going to change his mind. And the mere fact he was head of the klavern rendered him off limits to me as a potential Klan informant, anyway; opening him, in the Bureau’s eyes, would be an endorsement that the FBI approved some actions taken by him in the klavern. That made him a target as opposed to a potential RI, or Racial Informant.

Instead, I stepped down from Hawkins to go after lower-ranking members as informants, kluckers who weren’t in a position to make us complicit in their actions while they snitched on the Klan. Otherwise, we were no better than they, condoning any number of heinous acts that may or may not pay off in the end. That’s called professionalism, the polar opposite of what I found was transpiring when I got to Boston.

In one instance, I worked diligently on a female klucker named Kathy Ainsworth who was an elementary school teacher in the Jackson school system. She hailed from Brooklyn, New York, and I used our common roots to get friendly. Kathy was also the girlfriend of Thomas Tarrants, a hit man for the WKKKKOM and a member of the Silver Dollar Club, the secret group responsible for most of the killings and bombings throughout Mississippi.

Kathy rejected my overtures initially; she was a racist but against killing, and knew full well what was going on. I appealed to her humanitarian side, challenged her with the question of what kind of role model she was for her students? By condoning Tarrants’s actions, I made her see she was also effectively complicit in them. As a former social worker, I was able to appeal to her moral side. She’d gone into teaching “to do the right thing,” and I was offering her the opportunity to do another right thing.

Through “fisur,” or physical surveillance, and other techniques, we found the hideout and factory where the Silver Dollar Club made bombs and planned attacks on the black and Jewish communities. After accumulating probable cause and evidence, we followed Tarrants and Ainsworth to Meridian, Mississippi, for their planned attack on the Meyer Davidson Synagogue.

Tarrants arrived at the synagogue, whereupon he got out with a satchel of explosives to be placed at the back of the building, leaving Kathy in the car. At the time, the FBI did not have exclusive jurisdiction, so we turned the takedown over to the locals, including the Mississippi State Police. The targets were bull-horned by these law enforcement officials and told to drop the satchel.

Outside, Tarrants opened fire with a 9mm machine gun, drawing return fire from law enforcement immediately. Kathy was shot and killed at the wheel of the car. Tarrants threw her out of the car and began a wild chase through town. He was captured and taken into custody after taking several shots to his legs and chest.

The information ultimately provided by him and others we drew into our net was instrumental in stopping the bombings and murders. Director Hoover gave us all commendations. My “attaboy” recognized my informant development and contribution to the arrest of none other than Sam Bowers himself, the mastermind behind all the Klan’s activities. Our real FBI investigative code name, Bombings in Mississippi, came to an end soon thereafter in what remains a crucial, game-changing moment for the civil rights movement that would be immortalized in the Gene Hackman film
Mississippi Burning.

To this day I feel ambivalent about what happened to Kathy. She had helped us nail Tarrants and ultimately Bowers, and she had given her life in the effort. On the other hand, she knew who these people were and supported them every way imaginable. While she may not have condoned killing, she was apparently a self-avowed racist who’d enabled the actions of Tarrants and others in causing pain and heartache for countless victims while terrorizing an entire region. I was sorry she’d been killed but I couldn’t let myself be waylaid by her death. No one forced her to take the wheel of the car that day, any more than the other times she’d been along for the ride on Tarrants’s murderous escapades.

I told the story of my experience with Bombings in Mississippi and ABSCAM to Morris and others to make them understand that the FBI cannot have the leader of an organization as an informant. Morris listened attentively but showed no sign that my message was getting through. Maybe he had learned to lie so well, he was successfully doing it to himself.

I wanted both him and Connolly to know going into the meeting with Bulger that they were operating under my rules and standards now. At that point I thought I had FBIHQ backing me up. I thought this play was mine to make alone.

Maybe Morris and Connolly’s smug attitudes should have told me something then and there. In retrospect, it was clear that they knew something I didn’t.

What I did know was that I was about to meet the gangster guilty of presiding over an unprecedented reign of terror throughout the city of Boston, much of it condoned and supported by two FBI agents who knew I was about to interrogate him.

“Here we are,” John Morris said, pulling up to Bulger’s condominium in Quincy.

7

QUINCY, MASSACHUSETTS, 1981

I directed Morris to stay in the car and “lay chickie,” a euphemism for watching someone’s back from my days at Mount Loretto. Morris responded with a look of bemusement. The truth was I didn’t want Morris present because I wanted to get an independent, objective assessment of Bulger. Morris, it was becoming more and more evident, was too enamored with Whitey to be anything but counterproductive to my task.

“You’re gonna like this guy,” he said one more time as I climbed out of the car in front of Bulger’s condo, reaffirming my decision.

Prior experience with informants conditioned me to know that Morris might actually be right. The informants I had developed and met through other agents have led me to believe that they were mostly decent people doing whatever they could to please for whatever motive: money, ego, revenge, or simply to avoid incarceration. I’ve learned over the years that there are good informants and bad informants. Good informants are all alike, while the bad ones are all different.