fb-pixel Skip to main content

Even in prison, ‘Whitey’ Bulger is pushing boundaries

Josh Pietrantonio said he and James “Whitey” Bulger became good friends after the gangster strolled into the prison’s art department and admired his work.

Read about the long and deadly career of James J. ‘Whitey’ Bulger

TUCSON — Even at 85 years old and locked away for life, James “Whitey” Bulger, America’s most incorrigible gangster, is still up to his old tricks.

As if taking a leaf out of a “Sopranos” script, Bulger faced allegations last summer of an improper relationship with a female psychologist who provided counseling to him and others at the high security US Penitentiary in Tucson, the Globe has learned. As a result, Bulger was abruptly transferred to a prison in Florida, and an investigation was launched into the actions of the young woman, according to several people familiar with the ongoing probe.


The probe is focused on whether she improperly accepted gifts from Bulger — autographed photos of himself and others — and whether she gave him preferential treatment, including helping him win approval to communicate with his girlfriend, Catherine Greig, who is serving time in another prison.

The latest twist in the never-ending Bulger saga also involves revelations that the gangster, convicted of killing 11 people while running a sprawling criminal enterprise in Boston, was treated as a macabre sort of celebrity following his arrival at the prison in the Arizona desert in January 2014.

The octogenarian autographed an inmate’s sketch of Marilyn Monroe that was offered for sale on eBay, posed for photos with fellow inmates, and loved to reminisce about his criminal past, which included a stint at Alcatraz and a place on the FBI’s 10 Most Wanted list.

In a rare photo of Bulger taken during a sanctioned inmate photo day at the Tucson penitentiary last year, he appears smiling and relaxed. The slender gangster is dressed in sweat pants, a long-sleeved white shirt, and a white baseball cap as he stands alongside an inmate holding a mixed media portrait of Elvis that the other inmate created in the prison’s art department.


Inmate Josh Pietrantonio said James “Whitey” Bulger signed his portrait of Marilyn Monroe as a joke. Handout/Boston Globe

But not long after that photo was taken, allegations that Bulger used his notoriety to curry favor with the psychologist, who is in her 30s, triggered a Justice Department investigation, according to several people familiar with the probe.

Based on a series of interviews with a half-dozen people with knowledge of various aspects of the investigation, the Globe has learned that agents from the Justice Department’s Office of the Inspector General separately confronted Bulger and the psychologist in mid-August about allegations that he gave her autographed mugshots and photographs during their private sessions.

Investigators are focusing on whether the psychologist did favors for Bulger, including lobbying for him to be placed in a single cell and helping him win approval to correspond with Greig while she was in prison in Minnesota. The couple were eventually allowed to write each other after wardens at both prisons signed off.

Investigators are also looking into whether the psychologist tried to make a profit by selling the autographed souvenirs or brought a cellphone into the prison and let Bulger use it.

The psychologist, who has denied doing anything illegal, has been barred from the Tucson penitentiary, but continues to be paid by the Bureau of Prisons while working from home. Federal authorities have yet to decide whether to seek criminal charges or internal disciplinary action against her. Staff are prohibited from taking gifts from inmates or bringing personal cellphones into federal prisons.


Tucson attorney Sean Chapman, who represents the psychologist, said he did not want to comment because there is an ongoing investigation. “We are going to let the investigation play out,” he said.

The Boston Globe is withholding the woman’s name because she has not been charged with any wrongdoing.

Bulger’s attorney, Hank Brennan, declined to comment on the investigation. The Office of the Inspector General, the Bureau of Prisons, and the US attorney’s office in Arizona also declined to comment, according to a spokesman for each agency.

Back in Boston, one of the former prosecutors who helped win Bulger’s conviction on racketeering and murder charges in 2013, said the new allegations are vintage Bulger.

“It’s no surprise that he’s still breaking the rules and trying to manipulate the system,” Brian T. Kelly, now a partner at the law firm Nixon Peabody, said when told of the ongoing probe. “He’s been doing that his whole life.”

Not everyone at the Tucson facility was enamored with Bulger. The aging gangster was allegedly attacked in his cell by another inmate last April and suffered a minor scratch on his head, according to two people familiar with the incident. Bulger spent the next two months in segregation while prison officials investigated the incident.

Still, by all accounts, Bulger, whose double life as a crime boss and FBI informant has become the fodder for dozens of books, Hollywood movies, and television series, has been reveling in his celebrity behind bars. Always known as Jim or Jimmy to his friends, he told fellow inmates to call him Whitey — a nickname he used to hate — and waxed nostalgic about his gangster days.


Josh Pietrantonio, a 36-year-old inmate at the Tucson penitentiary, said during interviews by telephone and e-mail that he became good friends with Bulger after the gangster strolled into the prison’s art department last year and admired a portrait of Marilyn Monroe that he had created with charcoal, paint, and colored pencils.

“He would come down to the art room most nights and sit and watch me do artwork,” said Pietrantonio, a talented artist who likes to sketch Mafia figures and movie stars from the 1950s and 1960s. “I really enjoyed his company. Some nights we just sat on a bench outside and talked about life.”

Pietrantonio, who is slated to be released next year, said he jokingly asked Bulger to sign his mixed media portrait of Marilyn Monroe months ago, and his friend happily obliged – scrawling his name prominently on her neck.

“He just did it as a joke,” Pietrantonio said. “It wasn’t a big deal. I wasn’t doing it to make money. I just thought it was cool. I figured one day I’d show my kids. He’s an American legend in the Mafia.”

All told, Pietrantonio estimated that Bulger signed 10 to 15 pieces of artwork for him. And when Pietrantonio’s cousin was getting married, he said, Bulger wrote the couple a letter at his request congratulating them on their upcoming wedding.


Pietrantonio said he sent the autographed Marilyn Monroe picture to a friend. It later surfaced on eBay with an opening bid request for $250 – and the seller tossed in a photo of Bulger and Pietrantonio posing together at the prison for free. (The Globe, which does not pay for information or interviews, but routinely buys photos, placed the winning bid of $250 for the artwork that accompanies this article. The seller said he planned to use the money to help Pietrantonio pay for permitted essentials in prison.)

Pietrantonio said he almost got into trouble for creating a 19-by-25-inch picture of Bulger as he looked as a young man, with Alcatraz prison and the ghost of Al Capone lurking in the background. He said he was questioned by prison officials about whether Bulger paid him to do the artwork, and assured them that he hadn’t.

The warden confiscated the Bulger painting, according to Pietrantonio, who said he was warned, “You can’t be drawing him.”

There are numerous bits of Bulger memorabilia offered on eBay and other websites, ranging from Bulger’s FBI wanted poster to Boston newspapers from June 2011 proclaiming Bulger’s capture in Santa Monica, Calif., after more than 16 years on the run. Prices vary from the paltry to the pricey – and many have drawn no bids.

Bulger, however, puts great value on his image and words. In letters Bulger sent to a friend when he was in a Plymouth jail following his capture, he boasted that his letters would be worth a fortune some day and encouraged his pen pal to sell them on eBay.

Retired Massachusetts State Police Detective Lieutenant Bob Long, who spent years targeting Bulger, said he couldn’t comprehend why anyone would see value in Bulger memorabilia, considering how he tortured and killed his victims.

“Some people make it in the business world. Some people make it as athletes,” Long said. “He made it as a serial killer. He has no conscience about what he did to those people.”

Bulger is currently serving his sentence at Coleman II, a high-security penitentiary in Sumterville, Fla., located about 50 miles northwest of Orlando. His health has deteriorated since his 2013 trial in federal court in Boston, where he dressed in jeans and a shirt every day and occasionally shouted profanities at former underworld associates who testified against him.

He sometimes uses a wheelchair because he has difficulty walking, according to two people who are aware of his condition.

Pietrantonio, his Tucson prison pal, said Bulger’s past is behind him and that he viewed him as a funny, smart, likable guy. “You would just think he was an old grandpa,” he said.

As for Bulger’s current world view, Pietrantonio said, “He had a very positive attitude. He said he lived a good life.”


Kevin Cullen: In the end, everything has passed Whitey by

Photos: Whitey Bulger on trial

Whitey Bulger’s life in exile

Shelley Murphy can be reached at shelley.murphy@globe.com. Follow her on Twitter @shelleymurph.