What Whitey Bulger Can Still Teach Us

For me, Whitey Bulger’s arrest is more than vindication for a Boston FBI office tainted by the stink of old corruption. Whitey’s capture brings to the forefront questions that have remained unanswered for decades. Let’s take them in order.

1. What was Whitey’s relationship with Billy Bulger all those years? The Bulger brothers ran this town: Whitey as a mobster and Billy as state Senate president. Rumors had it that Billy could coerce a bill into passage by threatening harm from Whitey on any politician who didn’t see a policy Billy’s way. Billy has always said that’s nonsense and distanced himself from his brother and his actions. Black Mass attempts to prove more, with one scene in the book in which Whitey and Billy briefly meet. The Brothers Bulger is really about each man’s separate rise to power, and, for all of its suggestive title, doesn’t show them together and conspiring once they become powerful. In fact, Howie Carr, author of The Brothers Bulger, said this morning on NECN that it’s still unknown how much the brothers interacted over the years.

2. Who else in the FBI office did Bulger corrupt? David Boeri wrote a great story for Boston in 2008, just before FBI agent John Connolly, who became in essence one of Whitey’s henchman, stood trial for murder. The piece’s theme was that Connolly shouldn’t be the only agent facing Judgment Day. John Morris, Connolly’s supervisor in the FBI, knew a lot about Whitey and his misdeeds. Some law enforcement types in Boeri’s story say the U.S. Attorney prosecuting the Italian mob, Jeremiah T. O’Sullivan, likely obstructed justice on Whitey’s behalf. Here’s Boeri:

Fitzpatrick can name at least 10 agents in Boston in the ’70s and ’80s he believes were corrupt. Kevin Weeks, who’s been called Bulger’s surrogate son, recalls Bulger bragging that he could call on six FBI agents any time who “would willingly hop in the car with a machine gun.” Not for nothing did Bulger wake up every morning, look out his window, and say, “‘I own this town,’” Weeks told me. The FBI and Justice Department were so entangled with Bulger and Flemmi that the two organizations fought the state police and Drug Enforcement Administration’s investigation of Bulger and Flemmi, and resisted the efforts of federal prosecutor Fred Wyshak to indict the pair. Only when the state police and DEA threatened to go public with this did the FBI and Justice Department join the case.

Many of these law men are retired. Some of them are dead. But a full accounting of the FBI’s corruption, from Whitey’s lips, would go a long way to conclude that sordid chapter of the FBI.

3. How did Whitey support himself all these years? He’s been on the lam since 1994. The last known credible sighting of him was in London in 2002. The feds last night found a “very substantial” amount of cash in Whitey’s Santa Monica apartment. Did he take even more than that with him in 1994? If not, who gave him cash over the years? And how exactly would Whitey access it?

This is what I want to find out over the coming days.