As far as true crime stuff, I read a lot of the stuff about Whitey Bulger/John Connolly fairly recently. If you haven't done any reading on it, you might want to start with Valhalla's Wake. It's a great book about the IRA and the connection with South Boston...but it was written as a red herring so that Bulger wouldn't kill the rest of McIntyre's family...pretty killer idea, in retrospect.
Then read Black Mass: The True Story of an Unholy Alliance Between the FBI and the Irish Mob for details about the connection to the FBI that inspired the Departed and other films, and see if you can get through Kevin Weeks' Brutal; My Life Inside Whitey Bulger's Irish Mob. If you're interested in the struggle in Northern Ireland and the IRA, you should also check Patrick Nee's A Criminal and an Irishman: The Inside Story of the Boston Mob-IRA Connection. Nee grew up about an hour and a half away from where I lived in Ireland.
There are a ton of other books on the subject, but I haven't gotten back to it. I do remember being surprised that so many in Southie were advocating freeing Whitey after he was finally arrested.
All manner of men came to work for the News: everything from wild young Turks who wanted to rip the world in half and start all over again -- to tired, beer-bellied old hacks who wanted nothing more than to live out their days in peace before a bunch of lunatics ripped the world in half.
Dr. Hunter S. Thompson
The Rum Diary