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Black Mass: Whitey Bulger, the FBI, and a Devil's Deal Chapter 16 Summary

How It All Goes Down

Secrets Exposed

  • With his marriage in shambles, Morris is now in a full-blown moral crisis.
  • He abruptly opposes "Connolly's bid from promotion to supervisor" despite having previously promised his support (2.16.1).
  • Instead, Jim Ahearn becomes the new supervisor of the Organized Crime Squad, which works out great for Connolly—Ahearn is a devoted buddy.
  • This is 1988, by the way, and reporters from the Boston Globe—including authors Dick Lehr and Gerard O'Neill—are working on a series on the Bulger brothers.
  • Some of them even wonder if Bulger might be an FBI informant...
  • Nah. Too unrealistic.
  • Still, they ask around just to check. Jeremiah T. O'Sullivan lies through his teeth and says no.
  • A few agents hint that they're on the right path, even name-checking Connolly in some cases.
  • In May, Morris agrees to meet O'Neill for lunch, though he stridently denies that Bulger is an FBI informant.
  • That is, until they sit down to eat.
  • As soon as they do, Morris spills the beans to O'Neill, who's in shock that he cracked the case before the appetizers even arrived.
  • The reporting staff of the Globe is "dumbstruck" (2.16.19). Before they can run the story, however, they need to vet it through other sources.
  • Two months later, after running the story by several agents, the Globe publishes its expose on the Bulger boys.
  • Notably, one installment investigates the close relationship between Whitey and the FBI, though it doesn't accuse him of being an informant.
  • The FBI is ticked, to say the least. One agent, Tom Daly, even threatens the reporters by implying that Bulger is looking to take them out.
  • In the end, however, the story blows over—as they always do.
  • Despite another victory, Connolly can't rest up yet.
  • He's also dealing with an internal probe from Bill Weld in the Justice Department, who for months has been receiving shockingly accurate calls from a woman who claims to have knowledge of Bulger's relationship with the FBI.
  • Weld resigns later that year, but his staff pick up where he leaves off, and soon enough the report lands smack dab on Connolly's desk. Another dead end.
  • Bulger is way cocky by now. One day, he tries to walk through an airport with over $10,000 in cash, getting into a fight with a police officer who tries to stop him.
  • Flemmi seems to be getting along great, on the other hand. He's taken up skydiving and travels the world. What a nice retirement for a gangster.
  • Connolly continues to meet with Flemmi and Bulger for dinner, despite being told not to, like, a thousand times. Morris is "now persona non-grata" in their little squad (2.16.67).
  • Still, there's trouble on the horizon. Despite the FBI's protestations, the DEA is pushing forward with a drug investigation into Bulger that began back in 1987.