Whitey Bulger, the ruthless leader of Boston’s Winter Hill Gang, had a criminal career spanning decades. Cold-blooded murders, extortion and drug-dealing were all associated with the gangster who ruled South Boston’s underworld from the ‘70s to mid-90s. What was less known was the fact he was an informant, and was being protected by his FBI handler, agent John Connolly. In December of 1994, then-retired Connolly tipped off Bulger that he was about to be indicted in a sprawling RICO case, and by early 1995, Bulger and his girlfriend, Catherine Grieg, disappeared. Over a decade later, with Bulger still on the lam, Special Agent Richard Teahan became the head of the FBI’s Whitey Bulger Task Force, where for five years he “‘lived, ate and breathed Bulger.” A day after the bureau’s PSA targeting Greig hit the airwaves in 2011, a tip that cracked the case came in, and the criminal couple was arrested in Santa Monica, California. Now, Teahan was tasked with not only bringing Bulger back to Massachusetts where he would face justice, but debriefing the mobster over his sixteen years on the run. For six hours aboard the DOJ’s private jet with Bulger, Teahan learned how exactly he survived all those years on the lam — and evaded law enforcement in the process. Retired Supervisory Special Agent Richard Teahan and Bob Ward, a crime reporter with Boston 25, wrote about the investigation and that conversation in “Face to Face with Whitey Bulger” and join “Forbes True Crime” to discuss.

Watch the full interview above.