Study Guide

Fred Wyshak in Black Mass: Whitey Bulger, the FBI, and a Devil's Deal

By Dick Lehr and Gerard O'Neill

Fred Wyshak

Perhaps the only federal prosecutor who acts like a federal prosecutor, Fred Wyshak is the man who finally takes down Whitey Bulger. Despite being born in Boston, his status as an outsider allows him to break down the barriers between Bulger and justice.

His experience working the streets of New York City doesn't hurt either. There, Wyshak developed "a decade's experience in making cases [...] by getting defendants to roll against each other." (3.17.17). This comes in quite handy when you're dealing with a triple-pronged conspiracy that involves the mob, the FBI, and a few state senators for good measure.

While many have tried and failed before him, Wyshak somehow manages to take Bulger down. But how? Here are a few reasons:

  • He has a "heat-seeking instinct for the weak link in any criminal enterprise" (3.17.19).
  • He operates on a need-to-know basis when it comes to sharing information with the FBI.
  • He doesn't balk from taking actions that could have political repercussions.
  • He overwhelms all foes with his rugged good looks.

Okay, so we're not sure about that last one, but consider it an educated guess.

Wyshak's handsomeness aside, it's ultimately both his skills as a prosecutor and his fearlessness in taking on the Boston political machine that allows him to drive the final nail into Bulger's coffin.