Bludgeoned Gambling Kingpin Whitey Bulger Hoped to Die Quietly in Sleep, Per Letters to Gangster Friend

Notorious South Boston gangster James “Whitey” Bulger may be the only person in history to have died because his health dramatically improved.

The gambling and extortion kingpin who spent 16 years on the run from federal authorities was beaten to death last month within hours of his arrival at the US Penitentiary, Hazelton.

According to The Boston Globe, the 89-year-old had been transferred to the West Virginia prison from a medical care Level 3 prison in Florida because he had become less fragile and no longer needed round-the-clock care.

He was also feeling well enough to make “direct, serious threats” to staff members, which hastened his transfer to West Virginia, according to the Bureau of Prisons.

Murdered by Inmates

Correspondence between Bulger and fellow gangster Charlie Hopkins, obtained by The Globe, reveal the former’s state of mind in the months leading up to his death. A July 2017 letter shows Bulger believed he was not long for this world and hoped for a peaceful death.

The former boss of the Winter Hill Gang complains of failing health but mentions he had refused prison medical staff’s offer to take him to a local hospital for treatment because he knew he would be shackled to a bed.

“I prefer to stay here and hope to get a peaceful death,” Bulger wrote. “One of those he Died in his Sleep kind (sic).”

As a longtime FBI informer who ratted on his enemies — largely the New England Mafia — the list of those that wished Bulger harm was a long one.

Bookie Extortion 

Bulger was protected for years by his FBI handler, John Connolly, who was ultimately imprisoned for complicity in the gangster’s crimes.

But in 1994, a joint task force of the DEA, Massachusetts State Police, and Boston Police Department launched a separate probe into Bulger’s gambling operations and began building a case against him.

It focused on largely on the illegal bookmakers, from whom Bulger’s gang extorted protection money.

“We decided that the best way to attack the organization was through the bookmakers,” said retired Colonel Thomas Foley, during Bulger’s 2013 trial. Bookies who refused to pay faced consequences “from being put out of business, to taking a beating to, at times, being killed,” said Foley.

Bulger was ultimately convicted of 11 murders committed in the 1970s and 1980s and received two consecutive life sentences.