Following a lifetime of crime, 16 years on the run, a lengthy trial, and five years in federal prison, officials announced today that James "Whitey" Bulger is dead at the age of 89. He was killed soon after arriving at a new facility in West Virginia — with the Boston Globe reporting that a fellow inmate with Mafia ties is being investigated for the crime. Bulger was, of course, Boston's most infamous criminal, who had been serving a life sentence for his involvement in 11 murders — although he was accused of plenty more.

Jim Braude was joined by Brian Kelly, a former assistant U.S. Attorney and the lead prosecutor responsible for putting Bulger behind bars and now a partner at Nixon Peabody; Peter Gelzinis, a former longtime columnist at The Boston Herald, who covered Bulger's trial and life extensively, and who is also a lifetime South Boston resident; and John "Red" Shea, who was in Bulger's Winter Hill Gang in the 1980s and 1990s and spent 12 years in prison for cocaine trafficking.