The second job of any intelligence organization, after identifying where danger lies, is to protect its secrets. In theory the secrets are being kept from enemies so that the organization—the Federal Bureau of Investigation or the Central Intelligence Agency, say—can pursue the rest of its important work, but in practice the secrets held most tightly are those that can wreck careers, let cats out of bags, or bring a halt to operations—the secrets of failure kept from public exposure. The glacial progress of the investigations of the two most damaging spies in American secret history, Aldrich Ames at the CIA and Robert Hanssen at the FBI, may be explained in part by the queasy certainty of high agency and bureau officials that they were going to catch unshirted hell when the news got out. Of course, the longer the wait the worse the explosion, but who wants trouble today when it can be put off until tomorrow—and maybe even left to ruin the career of the next person to fill the job?
Hiding trouble seems to be part of the ethos of intelligence agencies, especially at the FBI, which rejected and denied all criticism during its half-century under J. Edgar Hoover, the strange celibate who built the bureau in his own crabbed image. “Investigation” was the mission he hid behind: he insisted the bureau only collected facts—it did not interpret them. Filed in his “Do Not File” file were the capital’s most embarrassing personal secrets; when he acquired a juicy one he made sure the subject knew about it—a main reason why no president dared fire him, although several wished to, and why congressional committees rarely turned down his budget requests.
Personal survival was Hoover’s first goal but the second was to protect America from the kind of internal decay which fire-and-brimstone orators of yesteryear used to call “moral pollution.” For decades, as recounted in Ronald Kessler’s history The Bureau, Hoover detested all those he considered un-American—most famously godless socialists and Communists—and found ways to hound and torment them; but Hoover’s deepest loathing was reserved for “sexual perverts,” Negro agitators like Martin Luther King Jr., and civil libertarians who denounced the bureau’s appetite for gossip, rumor, and innuendo.
Still, Hoover, who died in office in 1972, was both rigid and adaptable. When public enemies changed he did, too, and by the mid-1960s the bureau was seeking telephone wiretaps, bugs, mail covers, and especially confidential informants who could deliver intelligence about the Ku Klux Klan and the loosely organized families of Italian-American gangsters known as La Cosa Nostra (“Our Thing”) or the Mafia, an old word which has no accepted translation. For years Hoover resisted pressure to go after organized crime, fearing that the bureau’s special agents would be corrupted by Mafia money. But Robert F. Kennedy, United States attorney general under his brother Jack, refused to take no for an answer, and eventually the FBI began to pursue the Mafia with all the energy, and many of the same techniques, it had brought to bear in Hoover’s long campaign against the American Communist Party. There used to be a joke in the 1960s that half the Communists at Party meetings were reporting to the FBI on the other half, and the joke was not far short of the truth. The Mafia was harder to penetrate but the technique was the same—find somebody on the inside, get close, and turn the screw.
Confidential informants are really the same as spies—persons with a nominal allegiance or at least access to a targeted individual or group, who are willing to provide investigators with secret information, usually in return for money or preferment. FBI agents are trained in the art of recruiting informants at the bureau’s academy in Quantico, Virginia, and what they are taught is very similar to the techniques learned by CIA trainees at Camp Peary a little farther down the Virginia coast. For both organizations, rule one in agent-handling is control. Money helps, loyalty is nice, and shared ideals make everybody feel good, but the bedrock of control is fear and the purpose of control is to keep the handler and his mission on top.
Agent-running is not about making friends; it is about collecting information for the purpose of law enforcement or national security. FBI Special Agent John Connolly built a dazzling reputation in the Boston field office during the 1970s and 1980s as a consummate recruiter and handler of confidential informants who provided information used to prosecute bosses in the Italian mob, a top priority of the bureau once Hoover had finally been brought to admit that the Mafia actually existed. Connolly was a native son, born and raised in South Boston (“Southie”), where the Irish mob ran the gambling, loan-sharking, and drug business. A childhood friend of many who ended up on the wrong side of the law, Connolly was a sharp dresser who liked a good time, was easy and affable in manner, and had more brass than brains. Most important, he had a pipeline into the world of Boston mobsters and he helped his bosses make the kind of cases that get headlines.
According to Dick Lehr and Gerard O’Neill, Boston Globe reporters who expanded their investigative journalism on the Irish mob into an important book called Black Mass, Connolly was for years the golden boy of high bureau officials including FBI Director William Sessions, whose troubled tenure finally ended when President Clinton took the overdue step of firing him. In 1989, Lehr and O’Neill write, Sessions “traveled to Boston to personally congratulate the Boston agents, singling out Connolly for his handling of informants.” Connolly investigated no major cases, ran no big programs, never had a desk in Washington. He collected information from confidential informants. “The way you solve crime, ninety-nine percent of it,” Connolly said in a radio interview, “is when people tell you what happened. I mean, every director of the FBI has said that informants are our most important resource.”
Connolly’s most important resource was his fifteen-year relationship with James (“Whitey”) Bulger and Stevie (“The Rifleman”) Flemmi, which began in 1975 and ended, officially at least, with Connolly’s retirement in 1990. Bulger, a few years older than Connolly, was the brother of William Bulger, a leading Massachusetts politician who for many years ruled the state senate and is now president of the University of Massachusetts campus in Boston. Connolly was a childhood friend of Billy’s and knew Whitey, whose early life in crime graduated from robbing trucks to robbing banks before it was interrupted in 1956 by nine years in jail, served in federal penitentiaries in Atlanta, Alcatraz, and Leavenworth, where he is said to have taken part in an experimental CIA drug program using LSD. When Whitey got out of jail in 1965 his brother got him a job as a custodian in a Boston courthouse, but Whitey wanted more out of life than a broom and a janitor’s pay and he soon resumed his life of crime, starting with bookmaking.
If spies catch spies, as the mole hunters like to say, then criminals catch criminals, and in 1975 John Connolly, recently transferred to the organized crime squad in the Boston field office, successfully recruited Whitey to help him catch the Mafia gangsters who were the bureau’s top priority. The moment of recruitment is called “the pitch”; it involves both a request and an offer. What Connolly wanted was information that the FBI later used to put away the Angiulo brothers, who ran the rackets in Boston’s North End.
But what Connolly offered was not immediately clear to others. In theory confidential informants help out because they are in a squeeze—facing indictment and a long jail term. Sometimes, in a modest way, they are paid, or they are given a pass on minor offenses that are integral to the pattern of crime they are helping to shut down. But Whitey wasn’t in a squeeze, he never got paid, and his ongoing crimes were far from minor. So what lay behind this unholy pact between the FBI and an Irish mobster? What did Whitey get in return for committing the one sin Southie would never understand or forgive—talking to the cops?
Dick Lehr and Gerard O’Neill of The Boston Globe played a significant part in finding the answer to this question, beginning with a story in the Globe in 1988 about the brothers Bulger—one a powerful and respected politician, the other a criminal. But what the reporters found still stranger was Whitey’s apparently charmed life: the Boston Mafia was being pulled down by the FBI in one high-profile case after another, but nothing seemed to stick to Whitey. It was hard to explain unless somebody was protecting him. In May 1988 O’Neill was stunned during an interview when an FBI supervisor, John Morris, suddenly dumped the answer on him—James “Whitey” Bulger was an informant for the FBI, he had grown close to his handler, John Connolly, and it wasn’t luck that protected Whitey from the law. A second FBI source confirmed Morris’s story and the Globe published it in September. The bureau naturally denied the connection. “That is absolutely untrue,” said Jim Ahearn, the special agent in charge of the Boston field office. “We specifically deny that there has been special treatment of this individual.”
But once tugged, the thread of Bulger’s special relationship with the FBI continued to unravel and in 1998, during an extended federal court hearing, the story emerged in copious and painful detail. By that time Whitey and his partner Stevie Flemmi had been indicted on federal racketeering charges. Whitey disappeared in 1995 and his whereabouts are still unknown, but Flemmi was picked up when he unwisely tried to sneak back into Boston. At trial his lawyer offered a novel defense: nothing Flemmi did during the years of racketeering covered by his indictment was unknown to the FBI, which was using him and the missing Whitey as informants, and what had been overlooked then could not be charged as crimes now. Federal Judge Mark Wolf eventually rejected that claim and Flemmi in due course was convicted and sentenced to prison for life. But the judge’s 661-page ruling on the FBI’s handling of Bulger and Flemmi, backed up by 17,000 pages of sworn testimony, starkly revealed the terms of the unholy pact.
What Whitey Bulger got from John Connolly, and by extrapolation from the FBI, was immunity. It was a criminal’s dream: he got rid of many personal rivals and enemies, who were investigated, wiretapped, prosecuted, and jailed by the Feds, and in return he received timely information which allowed him to quit talking on phones as soon as they were wiretapped, to move his place of operations when it came under surveillance, and above all to deal in the time-honored manner with informers when they began to tell investigators about his crimes. Whitey and the Rifleman were eventually charged with twenty-one murders, eleven of them committed while acting as informants for the FBI, and three of those removed were men who had begun to talk to the FBI.