T.J. English: The Last Godfather

T.J. English is the author of five non-fiction books on the subjects of organized crime, criminal justice and the American underworld, including The Savage City, The Westies, and Paddy Whacked: The Untold Story of the Irish American Gangster. His journalism has appeared in Playboy, Esquire, New York, and other publications.

When legendary mobster James “Whitey” Bulger, 81, was nabbed earlier this week after nearly 16 years on the lam, it appeared to some as though the door slammed shut on the longest running show in the American underworld.

Even in his prime, from the mid-1970s to the mid-1990s, Bulger was a throwback. His criminal reign harkened back to the days of Jimmy Cagney and the Warner Bros. gangster movies of the 1930s. He was Irish American, his racketeering operation rooted in the insular, Old World neighborhood of South Boston. Though sometimes charming, with a carefully cultivated reputation as a “gentleman gangster” who looked out for the neighborhood, Bulger was, above all, psychotically vicious....

Among those seated in the courtroom at Bulger’s hearing on Friday was his brother William “Billy” Bulger, 78. For decades, there was no politician in the state of Massachusetts more powerful than the younger Bulger, who rose from being a representative from Southie to president of the state Senate. His rise to power in state politics paralleled the rise to power of his gangster brother, leading some to surmise that Billy had to be “connected.” Frequently investigated but never indicted, Billy was, in 2004, forced to resign from a cushy retirement job as president at the University of Massachusetts because of his brother’s tawdry reputation.

In the courtroom, the two Bulger brothers—who, presumably, have not seen each other in 16 years—shared a glance and a smile that seemed to encapsulate the mostly unspoken bond between the two that has spanned a lifetime.

The story of the two brothers has always been, and still is, deeply intertwined, as is the story of another man who was not present in the courtroom. John Connolly, also a child of Southie, was an FBI special agent who acted as Whitey Bulger’s handler with the FBI. Connelly is currently in  prison in Florida on racketeering and murder charges stemming from his relationship with Bulger....