James 'Whitey' Bulger Claimed He Was ‘Not Guilty’ And 'Vulnerable' In Letters To Pen Pal Now Up For Auction

Several lots of memorabilia that include letters, a prison-penned manuscript, and perhaps the last photos of James “Whitey” Bulger are being auctioned off by a former inmate who had befriended the late Boston gangster-turned-FBI informant in a federal penitentiary before his death.

The cache of Bulger memorabilia and correspondences are being auctioned at Lelands by his friend and former fellow inmate, Native American artist Clement “Chip” Janis. In the letters to Janis, the convicted killer writes that he’s “not guilty,” and  feeling “vulnerable” in prison; he also details his disdain over perceived unfair treatment from correction officers.

“Starting to get settled down after my stay in isolation,” Bulger wrote in a 2015 letter from Coleman Penitentiary in Florida. “Getting too old for that, 86 in Sept, and not guilty — but my word has no power over the reports of officer [sic]. Don’t even like to write about it makes me realize how vulnerable one is if someone takes a personal dislike to you. … A fight not of my choosing — hard to believe I have gone this far… Kind of a mystery to me — Why? Revenge?” he wrote in a missive to Janis.

James 'Whitey' Bulger mugshot in 2011. Photo: Getty Images

The former Winter Hill Gang boss was convicted in 2013 for his role in 11 murders. He had been on the run for 16 years prior to his 2011 arrest in California; he was tipped off in 1994 to a pending RICO indictment by his handler with the FBI. In November 2013, Bulger was handed two terms of life imprisonment plus five years. 

While imprisoned, Bulger was shuffled to multiple penitentiaries, and at one point met Janis, a self-taught Denver-based artist and member of the Rosebud Sioux Tribe of South Dakota. Clement had entered prison in 2006 on a weapons charge and soon dedicated himself to art while mentoring other inmates. He taught charcoal sketching and watercolor painting at the United States Penitentiary Tucson, where Bulger landed in 2014, as Boston Magazine reported last year. 

The two struck up a friendship in the prison art room, which led to ongoing correspondences as the former FBI Most Wanted fugitive was moved around the country. He wrote to Janis about his longing for his girlfriend, Catherine Greig, who was jailed at Waseca Federal Correctional Institution; according to Boston Magazine, while in Tucson, Bulger faced allegations of an improper relationship with a female psychologist.

“He was the master at charming people,” Janis told the publication.

The eight lots in the auction include an archive of handwritten correspondence, a 12-page handwritten book by Bulger titled "Joe Carnes aka 'The Choctaw Kid,” about Clarence Carnes failed 1946 Alcatraz escape attempt, the missive in which Bulger asserts that he is not guilty, and eight shots touted as the last known photos of the crime boss.

Bulger was violently murdered in prison in 2018 by two inmates, one of whom was a convicted hitman, as the Boston Globe reported. He was 89. 

The auction, which Lelands is calling the “Chip and Whitey Collection,” ends on April 2.