Review: Whitey – The Life of America’s Most Notorious Mob Boss, by Dick Lehr and Gerard O’Neill

The last in a trilogy of books about the notorious Irish-American mobster James ‘Whitey’ Bulger

Sat, Aug 8, 2015, 05:00


Book Title:
Whitey: The Life of America’s Most Notorious Mob Boss


Dick Lehr and Gerard O’Neill

Ebury Press

Guideline Price:

Some years ago I was fortunate enough to interview for this newspaper David Cornwell, better known as John le Carré. The conversation turned to his father, Ronnie, a notorious confidence trickster, whose funeral was attended by the great and not-so-good of the London criminal fraternity, one of whom laid a meaty hand on the younger Cornwell’s shoulder and intoned, “David, we was all bent. But your dad, ’e was very bent indeed.”

Some variation on that description might equally apply to the Boston mobster James “Whitey” Bulger, a man who, even by the low behavioural standards associated with the profoundly psychopathic, remains a man of spectacular unpleasantness. Under other circumstances it might have been a source of perverse pride to our small nation that the man whose position at the top of the FBI’s Most Wanted list was usurped only by Osama bin Laden should have held an Irish passport (his great-grandfather William Bulger came from Co Wexford), but even a cursory examination of Whitey Bulger’s crimes puts paid to any illusions of a Robin Hood thumbing his nose at the feds.

This is a killer and mutilator of women, a man who filled a personal cemetery by the Neponset River in Boston with his victims, and who is that most hated of criminal figures, the fink, the rat. This is no stand-up guy.

To understand the Boston that became Bulger’s fiefdom it’s important to recognise the impact of bussing, the well-intentioned if ultimately disastrous attempt to forcibly desegregate the city’s schools, particularly the decision to send black students from Roxbury High to white, Irish South Boston, and vice versa. The middle class of Southie reacted by fleeing to the suburbs, leaving an angry, insular Irish immigrant hard core ripe for exploitation. This would become the heart of Bulger’s empire.

Over the course of two decades, from the 1970s until the 1990s, Bulger took control of Boston’s criminal underworld, earning a fortune of $10 million-$20 million (€9 million-€18 million) through racketeering, extortion and drugs, while also finding time to run guns to the IRA in the ill-fated venture that ended with the capture of the Marita Ann, in 1984. In large part he became king simply by being more ruthless than any of his competitors.

Dick Lehr and Gerard O’Neill, the authors of Whitey, ascribe more than 20 killings to Bulger, from relatively routine hits – drive-by shootings and close-up assassinations – to more hands-on affairs: he stabbed the unfortunate Louis Litif, himself a murderer, 38 times with an ice pick, then shot him in the head just to make sure he was dead.

More disturbingly, Bulger appeared to enjoy strangling women. His closest associate, Steve Flemmi, lost two girlfriends, Debra Davis and Deborah Hussey, to Bulger in this way. Lest one begin to feel sympathy for Flemmi, he lured both lovers to their graves – and yanked out their teeth after death to hamper identification.

“Whitey is a vicious individual,” a report by the FBI noted in 1975, but he was fortunate in his choice of associates, none more so than in his relationship with the man who, by a coincidence of nomenclature, leads me to write this review: an FBI agent named John Connolly.

The mystery novelist James Lee Burke once observed that “if you give the devil an air conditioner, you’ll never get him out of the office”. Or, to put it another way, there are no small evils. In the 1960s the FBI became obsessed with taking down the Mafia. Boston agents took this as a cue to throw out the rule book, to the extent of coaching informants to perjure themselves in order to send innocent men – or innocent, at least, of the crimes of which they were accused – to die in jail. Flemmi, Bulger’s partner in femicide, had long been an informant for the feds, and it was he who brokered the early meetings between Bulger and Connolly, aided by the fact that Connolly, like Bulger, had grown up in south Boston, and idolised Whitey’s older brother, the oleaginous Bill Bulger, later to become president of the Massachusetts state senate.

Duplicitous Connolly was ambitious, and he knew that turning Bulger into a top-echelon informant against the Mafia would make his career. The cleverer, more duplicitous Bulger understood that by selling out his rivals he would help his own rise to the top of the heap. And if a little killing was required along the way, then so be it.

Bulger committed 11 murders on the FBI’s watch, and the bureau’s operatives, anxious to protect their source, were complicit in more than half of them. Connolly had created a monster, but he didn’t care. He was receiving commendations from his superiors on one hand and lucrative handouts from Bulger on the other. He even appeared in an instructional video for the bureau, in which he used the commendably Runyonesque term “a melancholy situation” to describe one in which the informant has more power than the agent.

This particular melancholy situation couldn’t last, however, especially when Bulger progressed from murdering low-level gangsters to killing “civilians”, including businessmen who crossed him and women who made the mistake of dating his colleague. In 1994 racketeering indictments were filed against Bulger and Flemmi. Connolly, by now retired from the FBI but still watching out for his old associates, managed to get a message to Bulger in time for him to flee, but Flemmi was arrested, as was Connolly. The FBI’s reputation was irreparably damaged, and further wounds were self-inflicted through subsequent stonewalling and incompetence.

Bulger vanished with his girlfriend, Catherine Greig, and managed to stay under the radar for more than 14 years, until he was eventually arrested in Santa Monica, California, and returned to Massachusetts, where, now that he is 85, he will almost certainly die in prison.

Whitey Bulger has been good for Lehr and O’Neill, as Whitey completes a loose trilogy that began with The Underboss, in 1989, and continued with the excellent Black Mass, from 2000, which has now been made into a film, with Johnny Depp as Bulger. Whitey should be their lap of honour, not least because the mobster’s apprehension in 2011 provides an ending for their tale, but its flaw lies in the very man who gives the book its name.

If you throw enough pollutants into a pond, then eventually you may end up staring at a three-eyed fish, but the fish itself will be less interesting than the factors that gave rise to its existence. Bulger, despite a personal history that includes multiple murders, the criminal rule of a city, incarceration in Alcatraz and the ingestion of LSD as part of a CIA-funded experiment on prisoners, is a kind of absence in his own biography, a psychopathic void defying understanding or definition. Even the death of his young son appears neither to alter nor, more importantly, to humanise him. He simply is, and soon he will cease to be. Whitey is almost certainly the best book that will ever be written about him, and should probably be the last. When he dies they’ll have to screw him into the ground.

John Connolly’s latest novel is A Song of Shadows