Cliff Notes for the Chattering Class: Whitey Bulger

AP Photo/Boston Police

Welcome to the first installment of a new Prospect feature, where we take a big chewy topic in the news and tell you everything you need to read about it to look like a smarty-pants at happy hour. First up, the Whitey Bulger trial! There’s no shortage of coverage of the unfolding trial proceedings, but you need a lot of context to understand the decades-long drama surrounding the mythologized South Boston gangster. As the trial continues, you should read Slate’s ongoing series, but if you want a handle on the story’s full Homeric sweep, read on.

The Three Essentials

1. Where was Whitey?

A piece from 1988, which highlights how the Winter Hill Gang’s influence looms heavy over South Boston, no one knows much about the legendary man—Bulger—leading it. As one observer put it, "People all knew him, but nobody knows him.”

2. Bulger and the FBI

This five-part series, reported in 1998, reveals the scope of Whitey Bulger’s relationship with the FBI, especially agent John Connolly, who put Southie neighborhood loyalty over his job when he tipped off the gangster that the federal agency was after him in 1995. The two decades-long symbiotic relationship between the criminal and the FBI for over caused the agency great embarrassment, and its culpability in the crimes Bulger is being tried for will likely be a focal point of this summer’s trial.  

3. Whitey in Exile

The Boston Globe’s 2011 story of Whitey and girlfriend Catherine Grieg’s years on the lam. In the13 years leading up to their capture, the couple posed as the cute retired couple Charlie and Carol Gasko, before a cat-induced friendship with an Icelandic model famous for Vidal Sassoon and Noxzema commercials finally proved the strange denouement to their life on the run.


If you don't have the patience to read multi-part epics, The New York Times has the Sparknotes version of the Whitey Bulger case in a three-and-a-half minute video. Many of the writers featured below make an appearance.

The Deep Cuts

  • Whitey Bulger’s brother was a Boston institution in his own right, serving as president (or rather the machine-style boss) of the Massachusetts senate for 17 years, and then president of the University of Massachusetts before her resigned in 2003. While Whitey was known for his various violent acts in South Boston, Billy Bulger (who prefers to be called Mister President, which is the name that comes up when you exchange emails with him) was known for his wit. Besides his career as an enormously powerful politician, he also wrote and self-published a pamphlet in 1986 declaring that journalism is the new terrorism (Joe Keohane described the dynamic between Billy Bulger and his least favorite columnist as “what Moby Dick would be like if the whale were as obsessed with Ahab as Ahab is with the whale.”) However, his brother’s crimes were the spark that fired his downfall at the hand of Mitt Romney. (“Seldom does the departure of a university president sound like a scene from a Greek tragedy or GoodFellas.”) Profiles of Billy are often far more illuminating than the more seamy portraits of his brother; a showcase of character can be far more entertaining than the mysterious absence of it. Plus, the elder Bulger has Ted Williams’ autograph, won outside Fenway Park after the slugger asked if the teenager was “a boo-er.”
  • Before ending up in Santa Monica, Bulger and Grieg took a pit stop on an island of the coast of Louisiana. Bulger was known there as “Uncle Tom,” cried when a puppy had to be shot, and traveled to the WalMart 40 miles away four times a week.
  • Eddie MacKenzie worked for Whitey Bulger from 1985 to 1990 “as a street soldier, an enforcer, a leg-breaker, a drug-runner. I was the hired muscle who distributed drugs for my boss and broke the limbs of those who disrespected him. I was often sent on missions that made me feel I was pushing up against the icy shoulder of death.”
  • Consulting WBUR’s database of the entire cast of characters, from the Winter Hill Gang to the principal FBI agents to all 19 of Bulger’s alleged victims, would be a smart plan. The main thing you learn from the brief snapshots is if Whitey is after you, don’t drink in a bar or drive anywhere. It will not end well.
  • At the Santa Monica home where Bulger and Grieg hid as a retired couple, they were only two miles away from where the gangster’s niece, Mary Hurley, lived in 1992, and only a few miles from the Los Angeles FBI bureau. However, the couple did more brazen things to mock the authorities. In 1995, he visited San Francisco with Grieg and they took a tour of Alcatraz—where he spent three of his nine years in prison for bank robbery in the late 50s and early 60s. The tourists took a joke picture behind bars, complete with black and white jumpsuits, to remember their trip. Bulger also asked a NYPD officer for directions for a good time that year.
  • He also taught his neighbor in Southern California the particulars of beard maintenance and gave him his old Stetson.
  • Irish Alzheimer’s defense: “That’s where you forget everything but the names of your enemies. The point of the trial is not to defeat the charges and emerge a free man, but to get back at as many people as he can.” Bulger is also claiming “being Irish” as his alibi.
  • Boston’s Bulger Task Force, formed in 2000, searched for the gangster in Europe, South America, and Asia.
  • In 2007, the FBI received a tip that Whitey Bulger had been seen at a movie theater in San Diego. The film he reportedly watched? The Departed.
  • If you don’t have the time to read anything about the Whitey Bulger case, The Onion sums it all up quite succinctly.

The best sentence from the Whitey Bulger archives

"He was a mobster, but so what? Everybody's got an occupation."

This video of Southies reacting to Whitey’s capture is a beautiful thing. The New York Times also interviewed locals after Whitey’s arrest: “Allegedly he did a lot of bad stuff. I don’t know, but he did some good stuff, too. Even my mother, who passed away at 93 a few years ago, would say, ‘Why do they treat Whitey that way? He was very nice and opened doors for me.’ ”

The Bar Story

“I walked into a liquor store once. And I look back at this, and I say, ‘What was I thinking?’ Because I didn't tell anybody. I had just left the Herald and I was new at the Globe, and so I'm thinking, how do I impress my bosses? So I said, I think I'm gonna go right down and meet Whitey. I can get there in three minutes from the Globe. I drive down Old Colony, park right in front, walk into the liquor store, thinking I'm going to find Kevin, because I knew Kevin. And there's Jimmy [Whitey's real name], behind the bar, I mean behind the counter. And there's nobody else in the store, it's just me and him. And I said, ‘Hi, Mr. Bulger. I'm Kevin Cullen from the Boston Globe. I know this is awkward, and maybe this is not the right time, but you know, is it possible that you and I could sit down and have a conversation?’ And he looked at me, not like everybody says, ‘Oh, he stared at you and you thought he was gonna kill you.’ That isn't the look he gave me. He gave me this look like, ‘Kid, what are you, out of your fuckin' mind?’ And he just looked at me, and then he sneered and he said, ‘Go fuck yourself.’ And I said, ‘Thank you, Mr. Bulger.’ And I left.”

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