In 1999, the FBI placed four men on its Ten Most Wanted list. The first, James Kopp, who murdered an abortion doctor, was apprehended in France in 2001. The third, Angel Resendiz, a notorious serial murderer known as the Railroad Killer, was located that same year and executed by Texas in 2006. The other two were slightly more difficult to find: Osama bin Laden and Boston gangster James “Whitey” Bulger.
At the time, bin Laden was being sought for his role in the bombings of U.S. embassies in Tanzania and Kenya and would elude capture until May 1, 2011. Bulger had it much easier, at least initially, as Kevin Cullen and Shelley Murphy detail in the exhaustive and captivating Whitey Bulger: America’s Most Wanted Gangster and the Manhunt That Brought Him to Justice. When the people chasing you — the FBI — also spent years enabling your criminal enterprise, it turns out it’s much easier to get a head start.
Bulger’s history as the leader of Winter Hill Gang — an Irish crime family born out of the Southie neighborhood in Boston — is well known and was even the basis for Jack Nicholson’s character in the Martin Scorsese film The Departed. Likewise, Bulger’s capture in a nondescript apartment in Santa Monica, six weeks after bin Laden’s death, led the national news. Still, Cullen and Murphy (both longtime Boston Globe reporters — Cullen a Pulitzer Prize winner, Murphy a George Polk Award winner) turn a story that has been largely public record into a tantalizing tale of cat and mouse, while highlighting the shocking duplicity of the FBI and Justice Department.
South Boston was filled with families that toed both lines of the law, hitmen and cops sharing last names and information, but even in Southie the Bulger family was unusual. There was Whitey, who started as a petty thief and graduated to robbing banks. It was a hobby that landed him in Alcatraz in the late 1950s, and eventually ended with him as Southie’s crime boss, a figure of intense fear, respect and more than a little folklore — he often posed as “a good bad guy,” which the book doesn’t exactly bear out. On the opposite side, seemingly, was Whitey’s brother Bill, a longtime Democratic politician who served as president of the Massachusetts State Senate and eventually became president of the University of Massachusetts. Yet it was Whitey who became “fused with the modern history of the city,” Cullen and Murphy write. “[T]here are few names better known or more deeply associated with the city than Bulger’s.”
The brothers were always reputed to have worked with each other, most notably during the busing crises of the mid-1970s, during the state’s attempt to desegregate Boston schools, which both men opposed violently — one literally, one figuratively. Cullen and Murphy never directly implicate Bill Bulger in any of Whitey’s dealings, but it’s clear the brothers loved each other and were fiercely (and in Whitey’s case, criminally) loyal to each other.
But not as loyal, it turned out, as the FBI was to Whitey. Decorated FBI agent John Connolly, also a Southie native, turned Whitey into an informant in what was at first the FBI’s decades-long quest to take out La Costra Nostra. The result was a blank check for Bulger and his associate Steve Flemmi to operate with impunity in Boston, the Feds turning a blind eye to (and often encouraging) the murders of recognized crime figures. The relationship between Connolly and Bulger turned far more collegial, to the point that they were essentially running a partnership, both men feeling more and more untouchable as the years wound by. Though the FBI may have enabled a madman, Bulger contained multitudes — devoted to his family, charitable, enjoyed reading and traveling the world, in addition to torturing and killing people — and Cullen and Murphy make it obvious he was well on his path of unchecked brutality with or without the FBI’s assistance.
By the time Bulger fled Boston in 1994, setting off a manhunt that wouldn’t conclude for nearly 20 years, the streets he’d ruled were already in the midst of gentrification, and Bulger’s workplace had shrunk — state-run lotto machines had dried up the bookie business and old ethnic divisions were disappearing — which makes Bulger’s flight from crime all the more tantalizing. I won’t spoil any details of Bulger’s life in hiding here, except to say that Cullen and Murphy do a brilliant job explicating what a judge called “16 years of extended banality.”
Whitey Bulger is nothing short of a masterpiece of true crime writing, relentlessly researched and cross-checked, historically fascinating and more than a little frightening. It’s not every day one gets to see the Boogeyman with the lights on. There no glorifying the monster in these pages, only the recitation of fact, which is brutal enough.
WHITEY BULGER: AMERICA’S MOST WANTED GANGSTER AND THE MANHUNT THAT BROUGHT HIM TO JUSTICE by Kevin Cullen and Shelley Murphy, Norton, 478 pages