Black Mass: Whitey Bulger, the FBI, and a Devil's Deal Chapter 15 Summary

How It All Goes Down

Connolly Talk

  • On February 8, 1988, Connolly runs into a reporter from the Boston Globe named Dick Lehr—who, if you've forgotten, is one of the authors of this book.
  • Connolly already knows Lehr because the reporter had written a story about the Organized Crime Squad last year, though it's not like they're best bros or anything.
  • Hence why it's so weird when Connolly decides to loudly announce that the FBI is bugging the Mafia again, this time in their new secret HQ at "Vanessa's Italian Food Shop" (2.15.6).
  • Lehr is shocked, not just about the bugging operation, but that Connolly is being so open about it with a reporter.
  • So Lehr does what any reporter should: he writes a story about it, though he doesn't explicitly name-check Connolly. The FBI is ticked off.
  • As it turns out, Connolly is playing a big role in the bugging of Vanessa's, but that's mostly due to the efforts of Flemmi, not Bulger.
  • But you can bet that Bulger gets the credit.
  • Flemmi also plays a big part in the first ever secret recording of "a Mafia induction ceremony" (2.15.31).
  • Again, however, all glory goes to Bulger.
  • Connolly would sometimes even protect associates of Bulger, like when he intimidates the police into dropping a murder investigation against a thug named Mark Estes.