How It All Goes Down
Win, Place, and Show
- The White Hill boys—including Howie Winter, Flemmi, and Bulger—are eagerly awaiting the results from the Suffolk Downs Racetrack, where they've rigged a race with "Fat Tony" Ciulla.
- Unfortunately for them, the paid-off jockey decides to win instead of losing, effectively tossing the gang's money down the drain.
- They beat the living tar out of him and called it a day.
- Here's how the scheme is supposed to work: Ciulla uses "bribes and intimidation" to force jockeys into specific outcomes, while the Winter Hill gangsters place big bets with a wide group of bookies (1.5.11).
- And bam—you now have a bunch of cash.
- Things go bad when Ciulla is busted by the FBI.
- In 1976, he decides to inform on the gang and go into the witness protection program.
- Because Bulger and Flemmi are now subject to a criminal investigation, they can no longer be active FBI informants.
- Uh-oh for Connolly's pet project.
- Connolly and Morris do all the paperwork to take Bulger and Flemmi off the books as informants, but never actually stop meeting them.
- They never even mention it to the gangsters.
- This is the first sign of corruption from the previously disciplined Morris.
- To be fair, he has bigger things on his mind: a probe into the "widespread hijacking of trucks in New England" called "Operation Lobster" (1.5.26).
- Sounds tasty.
- In the probe, an FBI agent named Nick Gianturco is posing as a purchaser of stolen merchandise. So far he's recovered around $2.6 million worth.
- One night, Flemmi mentions Gianturco to Connolly, not realizing that he's an undercover agent, and claims that some gangsters are considering taking him out.
- Connolly interprets this vague warning to an immediate threat and calls Gianturco in a panic, telling him not to go to an upcoming meeting.
- So he doesn't.
- Naturally, Connolly builds up the story bigger and bigger until Bulger and Flemmi seem like gosh-darned heroes.
- They saved an agent's life. Much wow.
- By 1978, however, the race-fixing case is gaining steam.
- Howie Winter is already in jail for unrelated charges, but Flemmi and Bulger are totally exposed.
- So, in January 1979, Connolly and Morris visit Bulger at his apartment, where Bulger falsely claims that he has nothing to do with the fixed races.
- And they believe him without question, because that is totally the right thing to do when investigating a criminal.
- The two agents visit Jeremiah T. O'Sullivan, the chief prosecutor in the case, and reveal that Bulger and Flemmi are informants.
- They also back Bulger's claim that he didn't fix any races.
- O'Sullivan takes some time to think about it, but ultimately decides to side with the agents and neglect to prosecute Flemmi and Bulger.
- Fat Tony is incredulous: he gave them everything they needed to prosecute the gangsters on a silver platter, and nothing?
- This is a joke.
- The investigation concludes in February and includes pretty much everyone in Winter Hill not named Bulger or Flemmi, though the pair does warn a few pals to skip town before the hammer comes down.
- That summer, John Morris decides "to host a party at his home" to celebrate Bulger and Flemmi being officially reinstated as FBI informants (1.5.74).
- As you can guess, his wife is ticked off.
- It's at this clandestine meet-up that Bulger and Flemmi get the impression that the FBI has given them a license to commit crime.
- After all, they're now unaffiliated after the fall of Winter Hill.
- So they decide to fill up this power vacuum themselves, "making the rounds to independent bookies" and forcing them to pay protection money (1.5.87).
- One such bookie is Burton K. "Chico" Krantz, one of the most legendary in the region.
- Connolly and Morris don't do jack to stop their informants from rising to the top of Boston's criminal underworld, however.
- Far from it—they act like friends.