As you may have heard, infamous Boston gangster James J. “Whitey” Bulger was killed in a West Virginia maximum security Federal prison on Tuesday, October 30th.
As the head boss of the Winter Hill Gang, Bulger was active in the late 1960s – early 1990s before fleeing to California with Catherine Greig after corrupt FBI agent John Connolly tipped him off about the FBI’s plans to arrest him.
If you’re unfamiliar with the story of Whitey Bulger, I highly recommend watching Black Mass (2015) – it’s a good introduction to what happened (though not entirely accurate). I would also recommend reading Whitey Bulger: America’s Most Wanted Gangster and the Manhunt That Brought Him to Justice by Kevin Cullen.
The story of Whitey Bulger was one I grew up with. My family hails from Dorchester, Quincy, the South End, Southie and Quincy – the hotspots of the Winter Hill Gang during its heyday. My grandfather, a Boston Police Detective in the 1960s, loathed Bulger (by all accounts) and made it a mission to chase him down in his younger years. As a result, I’ve been reflecting on my city recently, and how different it’s become since the days of Irish Americans dominating the streets of Southie.
As tribute to the city, and a final “sayonara” to Boston’s most ruthless mob boss, here are a few Boston and Massachusetts-based books that I love, and a map of places that each book corresponds to (day trip anyone!?):