As a man who ordered the murder of at least 19 people and spent more than two decades running one of America’s most deadly crime gangs, James “Whitey” Bulger is not someone most politicians would want an endorsement from.

But the notoriously ruthless Boston crime lord was, it seems, a big supporter of Donald Trump.

The gangster – who was murdered, aged 89, in prison last year – praised the US president in a series of letters written from his cell.

He called the entrepreneur-turned-commander-in-chief a “man of the hour”, and said he admired how he was “tough and fights back instead of bowing” to critics.

“He has,” Bulger wrote, “my vote so far”.

He meant it metaphorically: in Oklahoma where he served much of his life sentence, prisoners are not on the electoral roll.

The letters of praise came to light after their recipient, a nurse from Cape Cod, Massachusetts, named Janet Uhlar, passed them to America’s NBC News in an apparent bid to show a different side to the infamous gangster.

In one of the missives from August 2018, Bulger comments on Mr Trump’s foreign policy: “Feel China respects him and hesitant to try to bully him.”

In another, he refers to Robert Mueller‘s investigation into the president’s ties to Russia.

“Sorry to hear Trump is being boxed in by so many,” Bulger wrote. “Trump is experiencing what Mueller and company can orchestrate…[Mueller] should observe biblical saying, ‘Let he who is without sin cast the first stone’.”

The passage hints at a possible history between the two men. Mr Mueller was the FBI director when the agency was accused of protecting Bulger from prosecution in return for information on other gangs.

James “Whitey” Bulger as a young man (AP) (AP)

In another letter, the convict – once number two on America’s most wanted list behind only Osama bin Laden – refers to allegations Mr Trump paid off two women who claim they had extramarital affairs with the businessman.

“My bet is he’s happy with present wife and settled down,” writes Bulger. “No way would he wind up in Oval Office with a Monica Lewinsky. That was a scandal! Same media that attacks Trump would cover up for Bill Clinton.”

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The series of letters, sent over six years, also reflect on the gangster’s own life of crime and hint at his wish for a peaceful death – something he was denied when he was fatally bludgeoned by a fellow-prisoner at Hazelton penitentiary in West Virginia in October.

Before he was caught and convicted, Bulger was the head of the ultra-violent Winter Hill Gang which operated in Boston and neighbouring city Somerville from the 1970s to the 1990s, when he went into hiding after receiving a tip from a corrupt FBI agent that he was about to be arrested.

He eluded law enforcement for 16 years before finally being arrested in Santa Monica, California, in 2011.

Ms Uhlar started her pen-relationship with Bulger after she was a juror on his 2013 trial.