By Rich Schapiro, Kenzi Abou-Sabe and Robert Windrem
In the final months of his life, James "Whitey" Bulger wrote letters from prison offering his thoughts on a range of subjects.
His faltering health. His longtime girlfriend. His wish for a peaceful death.
But there was another topic that the notorious Boston crime boss returned to again and again: President Donald Trump.
In several handwritten letters shared with NBC News, Bulger expressed gushing praise for Trump, offering rave reviews of the president's foreign policy and combative relationship with the media.
"Trump is tough and fights back instead of bowing down to pressure — and caving in to press!" Bulger wrote in August 2018. "U.S. agrees with him press attacking and his reaction increases his popularity — He has my vote so far."
"History may show Trump was the man of the hour," Bulger wrote in a different letter earlier that month. "Feel China respects him and hesitant to try to bully him."
Bulger has been the subject of endless fascination, his life of crime and long flight from justice chronicled in countless newspaper articles, books and TV series. But his political views have largely gone unknown.
The legendary gangster, who was beaten to death inside a West Virginia prison cell last fall, was an ardent Trump supporter and fan of conservative media figures such as Rush Limbaugh and Sean Hannity, according to the letters shared with NBC News.
"I get some strange mail at times — a grandmother from Kansas — hates Trump wants him 'impeached,'" Bulger wrote in one letter. "She assumes I hate him? Why Because I'm in prison?"
The missive goes on to reference the allegations that Trump paid off two women with whom he had extramarital affairs. The aging gangster wrote that he believed Trump was a changed man and would never, for instance, engage in a romantic encounter with an intern in the Oval Office.
"My bet is he's happy with present wife and settled down," Bulger says in the letter. "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."
Bulger also railed against former special counsel Robert Mueller. An assistant U.S. attorney in Boston in the 1980s, Mueller went on to lead the FBI at a time when it was grappling with a sensational scandal involving agents protecting mob leaders like Bulger.
"Sorry to hear Trump is being boxed in by so many," Bulger wrote last August.
"Trump is experiencing what Mueller and company can orchestrate," Bulger said in a different letter from September. "[Mueller] should observe biblical saying - 'Let he who is without sin cast the first stone.'"
One month later, Bulger was dead.
The 89-year-old was fatally bludgeoned with a lock stuffed inside a sock in late October 2018. He was killed within 12 hours of his arrival at the Hazelton federal penitentiary in Bruceton Mills, W.Va., according to prison records obtained by NBC News.
No one has been charged in the killing, and federal prison officials have yet to explain why Bulger, an FBI informant, was placed in a general population unit at one of the country's most violent penitentiaries.
While behind bars, Bulger was a prodigious letter writer. In the weeks after he was sentenced to life in prison in 2013 for a raft of crimes, he began a correspondence with an unlikely person: one of the jurors who convicted him.
Janet Uhlar, a nurse who lives on Cape Cod, said the experience of sitting through Bulger's trial left her convinced that he was a murderer. But she was also troubled by the government's handling of the case, namely the deals that were cut with mobsters who provided what she found to be dubious testimony against Bulger in exchange for lenient prison sentences for serious crimes.
"I needed to hear his side of the story," Uhlar told NBC News.
Their correspondence got off to an uneasy start.
"No disrespect," Bulger wrote in his first letter to Uhlar in September 2013, "but I don't trust prosecutors, judges, jurors, FBI agents, CIA..."
But he was apparently won over by her skepticism of the case put on by Boston prosecutors. Bulger went on to send Uhlar more than 75 letters over the next five years.
Most of them were written in a flowing cursive that filled every inch of lined papers; a few he penned in tiny block print.
Writing from his cell, often deep into the night, Bulger mused about his mortality.
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"All I want is peace and quiet for these last days and sit out on prison yard in my wheelchair," Bulger wrote in a letter written two months before his murder. "...Good friends 'lifers' went out that way under blue sky."
He ranted against Boston prosecutors and the mob turncoats who testified against him.
He furiously denied ever killing women or working as an FBI informant.
He fondly recalled his life on the outside — even with the ever-present threat of arrest or an unnatural death.
"I loved to travel and appreciated it always," Bulger wrote. "The thought — enjoy while I can can end in a flash or in prison — always there but made me appreciate each day more."
In time, he and Uhlar developed an emotional bond. After her 26-year-old son died of a drug overdose in 2014, the once-feared gangster sent letters with long passages offering words of consolation.
"I'm glad your family are there for you, Janet," he wrote in January 2015. "I'm sure Josiah would want you to understand he loved you and in desperation wanted to have a period free of pain."
"Poor Josiah suffered terribly for a long time searched for Relief and it led to this," Bulger added.
Throughout their correspondence, he also sent Uhlar keepsakes, including a tongue-in-cheek "Christmas card" that he said was created by his niece. "She has a good sense of humor," he wrote on the back.
Bulger also shipped off to Uhlar a photo of him in prison when he was a much younger man. On the back, he documented his short-lived attempts to step away from the criminal life.
"This was my final prison picture close to graduation and have to go out in the world to compete," Bulger wrote. "1st job 1.25 an hour in a noisy paint shop — 2nd and final job union laborer 3.65 an hour — After that went back to what came naturally."
Bulger terrorized the Boston-area in the 1970s and 1980s as the leader of a local gang. He vanished in 1995 after a corrupt FBI agent tipped him off to an impending indictment. But 16 years later, federal agents tracked him down to a modest apartment in Santa Monica, Calif., where he was living with his longtime girlfriend, Catherine Greig.
In his letters, Bulger referred to Greig constantly. After pleading guilty to harboring a fugitive, she was sentenced to eight years in prison — a punishment that still rankled Bulger years later.
"My No. 1 interest is Catherine's health and freedom — hurts to see her here and stoic," Bulger wrote, referring to how she was dealing with life behind bars.
He sent Uhlar a photo of Greig — holding their two pet poodles, Nikki and Gigi — with a tender message written on the back.
"Catherine love of my life," it said. "We loved these beautiful creatures — had a humbling effect on me. Made me feel and in our 16 years on the run Catherine did for me what the police beatings, prisons couldn't kept me Crime free for 16 years and Happiest of our lives."
The letters shed new details on the couple's time in hiding, describing a serene existence marked by sweet gifts and soothing music.
"Catherine would decorate the apt for holidays — small tree little thoughtful gifts one year Bose Radio," Bulger said in a letter. "She had to go long distance for + carried it home — surprised me Christmas Eve — great gift had ear phones and put disco on with Gershwin music Rhapsody in Blue would put me to sleep."
But, as Bulger noted in the next line, the threat of violence always loomed. "Slept with gun on bed in case they came in shooting," he wrote.
The letters also revealed a little-known side of Bulger: he had a deep affection for children and animals. Bulger described making regular visits to a mall near their apartment in Santa Monica.
"We would sit in there listening to holiday music and enjoyed watching people with their children shopping — happy — cheered Catherine and I — normal life!" he wrote.
But the letters also contained many hints of darkness. Across multiple missives, he described the effects of allegedly having been subjected to a secret CIA program, code-named MK Ultra, while locked up in an Atlanta federal prison in the 1950s.
As part of the government's effort to develop a mind-control weapon, Bulger said he received LSD injections, leaving him with lasting hallucinations and insomnia.
The CIA confirmed the existence of the program in the 1970s. Inmates at the federal penitentiary where Bulger was held in Georgia filed suit in the 1980s, saying they had been dosed with LSD as part of the program in the 1950s and 1960s. A judge ruled in favor of the government, citing the statute of limitations. A U.S. official familiar with the program noted that CIA records are incomplete but that any participation by Bulger would have been voluntary.
"Nightmares no control," Bulger wrote. "Have them any and all times I doze or deep sleep — Gift from CIA MK Ultra."
Uhlar was taken aback by his candor. He even admitted to crimes, including murders, that he was never charged with committing.
Uhlar also found him to be surprisingly thoughtful and funny and compassionate.
"He is a criminal and he would frequently remind me of that. He didn't want me to lose sight of that," said Uhlar, who also visited him in prison three times. "But there was also a very compassionate side to him, a very gentle side that I saw both in the letters and in person when I spoke to him."
Uhlar said she shared the letters with NBC News in the hope of shining a light on the government's treatment of Bulger.
"Did our own government cause him to kill?" said Uhlar, who published a novel based on her experience on the trial called "The Truth Be Damned." "What might have become of him had they not subjected him to the LSD for so long?"
Uhlar, like many current and former federal prison staffers interviewed by NBC News, also has questions about Bulger's transfer to the West Virginia prison where he was killed. He was moved from a Florida prison known as a safe haven for inmates with targets on their back.
In April 2018, officials at the Coleman II penitentiary requested that he be sent to a federal medical facility, but it was rejected by the Bureau of Prisons, according to records obtained by NBC News.
Bulger's medical classification level was then lowered, the records show, despite his advanced age and a history of heart problems. Some current and former federal prison staffers have speculated that the change was made solely to make it easier to move Bulger to a different facility.
The Bureau of Prisons has said that Bulger was transferred from Coleman because he had threatened a nursing supervisor in February 2018. The prison's former warden, Charles Lockett, told NBC News that Bulger's medical classification was altered because he refused to see a specialist.
"They couldn't make a decision whether he was sick or not," Lockett said.
But Bulger's letters tell a story of a man who was seriously ill. After the incident with the nursing supervisor, the 88-year-old inmate was sent to solitary confinement.
His stint in isolation was supposed to last for 30 days but he remained there until his transfer to West Virginia eight months later, in October 2018.
Bulger, who claimed to have suffered eight heart attacks, said he was regularly downing nitro pills and taking oxygen to keep his chest pains at bay.
"The sharp piercing shock pains in heart every so often remind me of my chances and clock running out — 'father time' — the grim reaper is just a few steps behind!" Bulger wrote to Uhlar that August.
"I still get chest pains after I eat meals if I lay down — have to take nitro and hope this isn't 'No. 9.'"
In that same letter, Bulger brought up Trump multiple times.
"Media is a bigger problem than Trump," he wrote. "Through U.S. history the media's hunger for scoops and headlines has cost the lives of U.S. servicemen. Can cite examples."
"Trump is fortunate to have loyalty of [conservative commentator Bill Cunningham], Rush Limbaugh + Hannity AKA 'Little Rush,'" Bulger said in the same letter.
After signing off and adding a brief postscript, he wrote:
Wonder if Mueller thinks of me?
Give my regards to the President!"
Rich Schapiro is a reporter for the NBC News Investigative Unit.
Kenzi Abou-Sabe is a reporter with the NBC News Investigative Unit.
Robert Windrem is an investigative reporter/producer with NBC News, specializing in international security.