Testimony has now begun in a Boston court in the trial of FBI most wanted crime boss and informant James “Whitey” Bulger. Bulger is accused of committing nineteen murders and a laundry list of other crimes. Check out coverage of the trial’s opening and some context in CNN, The Washington Post, and The New York Times. A good deal of the evidence that will be introduced by the prosecution and the defense is described in the recently published Whitey: The Life of America’s Most Notorious Mob Boss by Dick Lehr and Gerard O’Neill, which former federal prosecutor, defense lawyer and author Ron Liebman reviewed in April.

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James J. “Whitey” Bulger, who became the FBI’s most-wanted fugitive after Osama Bin Laden was taken down, was captured at age 82 in June 2011, after he and his girlfriend spent 16 years on the run. He now sits in a jail cell, awaiting trial, and most likely will spend the remainder of his life behind bars.

Bulger was the brutal, indeed monstrous, crime boss of the Irish mafia in South Boston. There is an oeuvre of Whitey Bulger books, news stories and fictionalized accounts. Not only have professional writers contributed to this mass of material, but several of the gangsters associated with Whitey have also tried cashing in on the legend with their own collaboratively written books. Even his brother Bill (more on him later) has written a memoir. There is also is at least one Whitey website.

Two new Bulger biographies were recently published within days of each other. Both were written by co-author teams who either were or still are associated with the Boston Globe. I read the one written by Dick Lehr (Boston University professor and former Globe reporter) and Gerard O’Neill (Pulitzer Prize-winning former Globe editor), who also co-authored an earlier Whitey book: Black Mass: Whitey Bulger, The FBI, and a Devil’s Deal, soon to become a movie starring Johnny Depp. (The authors report that, while Bulger was on the lam, someone thought he spotted Bulger leaving a movie theater showing the Oscar-winning film “The Departed,” in which Jack Nicholson plays a Boston gangster bearing more than a casual resemblance to Whitey.)

Lehr and O’Neill start at the very beginning, tracing the Bulger ancestors’ early migration, from Ireland to Newfoundland and then eventually to Boston. The Boston neighborhood populated by so many of these immigrants was known as Southie.Mercifully, the authors spend little time on this family-tree analysis, but with enough detail for the reader to put in focus the picture of the classic Irish working-class experience with its strong quest for survival and search for a better life. Whitey Bulger’s story is a kind of rags-to-riches tale, but one from the dark side. The authors take his story, from his juvenile delinquency through his time in the ranks of Southie’s so-called Winter Hill gang, and then lead us step by step through his rise to the head of Boston’s Irish mob, his crime spree, his flight from justice and eventual capture. 

Along the way, we learn of Whitey’s time served for bank robbery, from 1956 to 1965, including a stint in Alcatraz. While in prison Whitey, a voracious reader, studied biographies of WWII generals. He seems to have taken much of what he learned about the need for stern (in his case brutal) leadership from his prison reading.

His real life of crime blossomed after his release: Whitey went from convicted bank robber to loan shark, drug dealer, protection racket chief and murderer. He ordered hits, often using gang member John Maritano as his assassin of choice, but also on occasion took matters into his own hands. With his crew of thugs — Maritano, Stevie Flemmi, Kevin Weeks and Frank Nee — Bulger’s reign of terror eclipsed even that of Boston’s North End Italian Mafia. 

But there was a kink in his life of crime. Whitey was a longtime FBI informant. Smarter than any of those around him, including FBI agent John Connolly, who had recruited Whitey as his high level “CI,” or confidential informant, Whitey managed to turn the FBI into his own personal insurance policy. He perverted Connolly, who grew up alongside Whitey in the projects of Southie and who is now serving heavy time after having been convicted in two trials for racketeering and murder. Connolly did more than provide carte blanche for Whitey and his crew to continue committing crimes; he also provided the names of those who had agreed to testify against Whitey. Each of these men was then murdered. 

Whitey had a penchant for using those in authority for his own benefit. Even before Connolly, Whitey used his brother Bill, who served as President of the Massachusetts Senate and then went on to become president of the University of Massachusetts before being forced to resign by then-Governor Mitt Romney after it was discovered that Bill had communicated with his fugitive brother. Bill had also interceded with then-Speaker of the U.S. House of Representatives John McCormack to lighten Whitey’s early prison time and, years later, seems indeed to have aided his older brother while he was on the lam.

Whitey Bulger’s life is a breathtaking story of brutality and corruption. He was responsible for at least 19 murders. To the authors’ credit, they take the reader through all this with a prose style that is at once matter of fact and yet paces this story like a motorist rubbernecking a bloody car crash. 

There are a few quibbles. Someone named Billy O’Sullivan is first described as having been killed in the street (three shots to the head) as he ran from his front stoop, and then a few pages later as having met his maker on Whitey’s lawn. There is a touch of armchair psychology when the authors write that the reason Whitey was so vicious with informers was his subconscious rage at having been one himself; although, that sounds right to me.

All in all, the incredible story of this murderous gangster has been fully presented and is very readable. 

Ron Liebman, a former federal prosecutor and defense lawyer, is the author of several books, including the novels Death by Rodrigo and Jersey Law (Simon & Schuster).

 

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