Black Mass: Whitey Bulger, the FBI, and a Devil's Deal Chapter 4 Summary

How It All Goes Down

Bob 'n' Weave

  • Paul Rico, Dennis Condon, and John Connolly all believe that Bulger and Flemmi are vital to the FBI's efforts to take down the Mafia, and will do whatever it takes to protect them.
  • During the reign of FBI director J. Edgar Hoover, the agency had notoriously ignored the Mafia in favor of political witch-hunts, and it's not until the '60s that things slowly begin to change.
  • In fact, Dennis Condon and Paul Rico are some of the first employees at Boston's "first-ever Organized Crime Squad," which TBH sounds like a supervillain dream-team (1.4.5).
  • The Squad sets their sights on Gennaro J. Angiulo, who runs the Mafia in New England.
  • Over the course of the '60s, Congress passes a series of bills meant to layeth the smackdown on the Mafia.
  • These laws allow the feds to more easily monitor Mafiosos through electronic means and charge them with federal crimes.
  • The big one is the Racketeering Influenced and Corrupt Organizations Act, better known as RICO. This law allows federal agents to send gangsters behind bars for decades if they can prove that they're involved in shady business dealings across multiple states.
  • Despite these fancy new legal tools, the most powerful weapons in the FBI's arsenal are informants. This is well attested to in the FBI's training material, and is highly encouraged by its internal culture.
  • The FBI uses a lot of electronic surveillance during this period, often in legally suspect ways. Because these illegally-acquired recordings often could not be used in court, the onus is still on informants to take down the mob.
  • Of course, there are tons of regulations meant to keep agents from getting too tight with informants, but there's enough wiggle room for guys like Connolly to weasel their way through.
  • Rico lets Flemmi get away with a bunch of crimes, for instance, many of them violent in nature.
  • Now it's Connolly's turn.
  • He's faced with another investigation into Flemmi and Bulger: a vending machine company called National Melotone is making complaints to the FBI that the two gangsters are intimidating local shop owners into using their vending machines, rather than the company's.
  • And of course Connolly is charged with investigating the claim against Bulger.
  • He intimidates the company's executives into dropping the matter and goes on his merry way.
  • Around this time Connolly starts acting weird—more like a "salesman" than an FBI agent (1.4.46).
  • He divorces his wife and move across the street from Bulger's girlfriend, Catherine Greig. Because that's not weird.
  • Some FBI bigwigs notice this behavior and assign Connolly a new supervisor, John Morris, who is seen as a potentially cooling force on the volatile Connolly.
  • Spoiler: it doesn't work.