Study Guide

Black Mass: Whitey Bulger, the FBI, and a Devil's Deal Chapter 1—Part I

By Dick Lehr and Gerard O'Neill

Chapter 1—Part I


  • An older John Connolly, now an FBI agent, is parking his beat-up junker in the town of Quincy, just outside of Boston.
  • He's meeting up with a "contact" (which we presume to mean "informant") who also grew up in South Boston, called "Southie" by those in the know (1.1.1).
  • Connolly has been a part of the FBI for a bit, but he was just transferred to his hometown a year ago, which was a welcome development for him.
  • As it happens, the FBI is in the midst of an internal crisis. The bureau has received a ton of bad press in recent years for secretly monitoring politicians and public figures.
  • Hmm, we wonder why.
  • To cover up this PR snafu (the understatement of the year), the FBI has set its sights on dismantling the Mafia, the Italian-American criminal organization that's dominating the underworld.
  • Finally, we learn the identity of Connolly's's none other than Whitey Bulger, the street tough from the prologue.
  • Another agent, Dennis Condon, had tried to turn Bulger into an informant a few years back in 1971, but failed harder than a basketball player working against the Based God's curse.
  • Now, however, it's 1975, and Connolly is confident that his neighborhood ties with Bulger will help seal the deal.
  • He begins his pitch in a rather unusual manner: by telling Bulger that he should make use of his "friends in law enforcement" (1.1.11).
  • Shady.
  • Turns out that Bulger could use a friend right now. Boston is experiencing some serious changes, not the least of which being a federally led effort to integrate its school system.
  • Many residents of Boston are in an uproar over this, and leading the charge is a certain local political leader named Billy Bulger—Whitey's little brother.
  • The criminal world is changing too. Whitey has sparked a relationship with the Winter Hill gang, particularly bonding with a ridiculously named mobster named Stevie "The Rifleman" Flemmi.
  • The Winter Hill gang, like the FBI, is currently beefing with Boston's resident Mafia, led by "the powerful underboss Gennaro J. Angiulo and his four brothers" (1.1.20).
  • So, basically, Connolly wants Bulger to rat out on the Mafia—which is a huge no-no in the criminal world.
  • After the meeting, Connolly asks Flemmi for advice, which is hilarious because Flemmi has been an informant since the '60s. He was recruited by Agent H. Paul Rico, former partner of Condon.
  • Although not officially in the Mafia, Flemmi has friends on the inside, like childhood buddy "Cadillac Frank" Salemme, and has been trading information for protection from the FBI.
  • In the late '60s, Flemmi had been wanted for several murders, but Rico would tell him when the feds were coming for him, helping him to stay on the lam for four years until the charges were dropped.
  • So, uh, this is just straight-up corruption, huh?
  • Flemmi isn't sure if Bulger knows this, but he heartily recommends that Bulger take up Connolly on his offer. Can't pass up a deal like that.
  • Two weeks later, Bulger agrees to the deal. This is a huge win for Connolly, as Bulger is a prominent gangster in the region.
  • And, absurdly, five weeks after that fateful handshake, Bulger commits his murder while on the FBI payroll—but far from his last.