How It All Goes Down
South Boston
- When he got back to Boston in 1974, Connolly learned that Bulger "was the preeminent Irish gangster" in Southie, which sounds like a great blurb for a LinkedIn profile (1.2.4).
- Connolly and Bulger had grown up in the same housing project in Southie—the first in Boston.
- South Boston has a unique culture defined by its Irish-American population. The Catholic Church is the center of social life, outsiders are heaped with scorn, and internal traditions are revered. People tend to stick around, too.
- Though Boston has been around for two hundred years, it doesn't become an Irish-American stronghold until after the Civil War, when they move into the city to find work, developing an often-contentious relationship with Boston's Italian-American population.
- Although the community starts off strong, developing a strong base of Church-centric social institutions, Southie is slammed by the Great Depression, as is the rest of Boston.
- In 1938, the Bulger family moves into Southie, which is still reeling from the aforementioned economic apocalypse. Whitey is eleven.
- James Bulger, Whitey's dad, had "lost much of his arm when it was caught between two railroad cars" (1.2.16). He was a quiet guy who kept to himself for the most part. Billy takes after him.
- Billy first runs for political office in 1960. He quickly rises the ranks in the state senate and "went on to be president of the chamber longer than any man in Massachusetts history" (1.2.19).
- Billy is a Southie guy, through and through. He fiercely fights to "protect" his community from outsiders, as with his opposition to the forced integration efforts led by the feds.
- When he was a kid, Connolly was tighter with Billy than Whitey, who Connolly only knew as a notorious neighborhood troublemaker.
- When Connolly is born, Whitey is thirteen, and he's already taking stuff from trucks to sell on the streets.
- Dang. We were mostly concerned about Pokémon at that age.
- Whitey has a long stint in federal prison when he's twenty-seven, and even ends up in Alcatraz, one of the most notorious prisons in American history.
- He's released after nine years, and immediately moves back in with his mother in her Southie apartment. Shaken by prison, Whitey promises himself that he'll never go back.
- After his release, Whitey works for Donald Killeen, a bigwig bookmaker. Bookmakers run illegal betting markets, by the way.
- Being a shady guy, Whitey betrays Killeen to earn cred with the Winter Hill gang, Killeen's chief rivals. And by "betray" we mean "assassinate."
- Yup. Whitey is one nasty character.
- Although Whitey has made a bunch of money and killed a lot of people, he lives a frugal, spartan lifestyle that set him apart from most of Boston's gangsters.
- That doesn't mean he's a nice guy. Bulger is feared across the streets of Southie, and Ellen Brogna, wife of Howie Winter, says that Whitey "chilled her" like no other mobsters (1.2.45).
- So, given their mutual Southie roots, it's perfect that Connolly and Bulger have ended up together. They're like two corrupt peas in a rotten pod.
- In fact, Bulger quickly breaks his own promise and starts informing on not just the Mafia, but also his fellow Irish mobsters. That's a huge no-no in the hood.
- Overjoyed, Connolly spreads Bulger's reports around the FBI to critical acclaim, not just earning cred for himself, but also the brutal Whitey Bulger.