Whitey Bulger apparently had a lot of thoughts about Donald Trump and the media

Prison letters shared with NBC News shed some light on the former Boston mob boss's political views.

James "Whitey" Bulger. –U.S. Marshal Service via The New York Times

James “Whitey” Bulger’s brother may have been a Democratic powerbroker in Massachusetts politics. But the longtime Boston mob boss himself seems to have been enamored with Republican President Donald Trump, at least during the final months of his life.

In handwritten prison letters, Bulger wrote admiringly about Trump, several conservative media figures, and the president’s combative relationship with the media, according to a NBC News report Saturday.

“History may show Trump was the man of the hour,” he reportedly wrote in a letter last August.

Bulger, who was serving two life sentences, was killed by fellow inmates shortly after being transferred to a West Virginia prison last October. He was 89 at the time of his death.


However, during his final years, Bulger wrote dozens of letters to Janet Uhlar, an Eastham nurse and sympathetic member of the jury that convicted him in 2014. According to NBC News, the subject often returned to Trump and national politics.

“Trump is tough and fights back instead of bowing down to pressure — and caving in to press!” he wrote in August 2018. “U.S. agrees with him press attacking and his reaction increases his popularity — He has my vote so far.”

Bulger — who had a contentious history of his own with the press — wrote that the media “is a bigger problem than Trump.”

“Through U.S. history the media’s hunger for scoops and headlines has cost the lives of U.S. servicemen,” he said. “Can cite examples.”

Bulger added that Trump is “fortunate to have loyalty” of Republican-aligned commentators like Bill Cunningham, Rush Limbaugh, and Sean Hannity, who he nicknamed “Little Rush.” He also claimed that the “same media that attacks Trump would cover up for Bill Clinton.” And despite the allegations that Trump has cheated on his current wife, Melania, before becoming president, Bulger expressed confidence that he wouldn’t get caught in a similar scandal as Clinton did in his second term.


“My bet is he’s happy with present wife and settled down,” Bulger wrote. “No way would he wind up in Oval Office with a Monica Lewinsky — That was a scandal!”

In the same letter (of which NBC published a photo), Bulger expressed support for a “strong military” and a “strong NASA,” which he said had been “dismantled by the Carter, Clinton, and Obama administration.

“They downsized military,” he wrote. “Regan[sic]-Bush-Trump corrected mistakes.”

The aging gangster was also reportedly confused by a letter he received that assumed he opposed Trump.

“I get some strange mail at times — a grandmother from Kansas — hates Trump wants him ‘impeached,'” Bulger wrote, according to NBC News. “She assumes I hate him? Why Because I’m in prison?”

Bulger even acknowledged that he and Trump also shared an adversarial history with another prominent figure: former FBI director and special counsel Robert Mueller. Mueller was the federal prosecutor in charge of criminal division of the U.S. attorney’s office in Boston during the 1980s, when Bulger was working as an FBI informant. However, its unclear if Mueller, who had become the FBI’s director by the time the agency’s use of informants had become a scandal decades later, knew at the time about his agents’ work with Bulger.

Still, in a letter last August, Bulger suggested Trump was getting “boxed in” by Mueller’s investigation. That same month, he signed off a letter with a reference to the special counsel.

“Wonder if Mueller thinks of me?” Bulger wrote. “Give my regards to the President!”