Black Mass: Whitey Bulger, the FBI, and a Devil's Deal Chapter 17—Part III Summary

How It All Goes Down

Fred Wyshak

  • The Mafia, now led by "Raymond Patriarca of Rhode Island," is in rough shape, and Bulger is once again ready to pounce (3.17.1).
  • Patriarca and co. will soon go to prison after the secretly recorded initiation ceremony mentioned last chapter is played in court.
  • Bulger will fill the void, as will Cadillac Frank Salemme, Flemmi's childhood friend.
  • Connolly leaves the FBI in 1990, taking a lucrative salary as "head of corporate security at Boston Edison," a major power company (3.17.4).
  • Where's karma when you need it?
  • Bulger and Flemmi decide to chill out for a bit, investing their illegally-earned money into actual business ventures.
  • Enter Fred Wyshak, a native Bostonian who's finally returned to his hometown after cutting his teeth as a US attorney in New York City.
  • Wyshak can immediately tell that Bulger is the big fish around these parts, becoming immediately suspicious when everyone tells him to focus instead on the Mafia, which is clearly not a threat to anything but the city's spaghetti supplies.
  • Wyshak pokes around for a while to little avail, until hooking up with Brian Kelly, another federal prosecutor. The pair becomes a dream team of sweet, sweet justice.
  • Things aren't easy though. In 1989, Wyshak tries to wiretap Howie Winter, who's been released from prison, and use him to get to Bulger.
  • Winter seems one step ahead of him, however.
  • Hmm...wonder why that is.
  • Wyshak tries again in 1992, and this time he leaves the FBI out of the equation entirely.
  • The operation goes off like a dream and Winter is convicted the following year.
  • This is a similar tact to that taken by state policeman Charles Henderson "back in the early '80s," in a failed attempt to take down Bulger (3.17.34).
  • By now, however, Henderson is the head of the state police, and he's ready to finish the job.
  • By focusing on nabbing bookies, then making their way up the chain of command, both groups are able to get closer and closer to Bulger himself.
  • Despite making progress, however, Connolly continues to inform Flemmi and Bulger whenever there's an investigation aimed in their direction, giving the crooks time to get away.