Whitey Bulger complained about a changing Boston in letters sold at auction

Whitey Bulger complained about a changing Boston in letters sold at auction
US Marshals
James "Whitey" Bulger in 2011

While notorious Boston mob boss James “Whitey” Bulger was in federal prison, he bemoaned the state of his old neighborhood in letters to a friend he met in detention.

“Someone painted this on a fence in South Boston many years ago,” he wrote in reference to a graffiti mural of a leprechaun smoking a pipe and holding an Irish flag. “Now South Boston is populated by rich college kids living in expensive condos. Weekends the bars have lines outside of them.”

The letters were part of a collection of memorabilia related to Bulger that were on the auction block through Urban Culture Auctions in West Palm Beach, Florida, on Sunday. The letters that Bulger wrote to former inmate Timothy Glass provide a glimpse into the years that the longtime fugitive and convicted murderer spent behind bars.

Rico Baca, the owner of Urban Culture Auctions, said Glass approached him about the letters about four months ago. After reading the letters and verifying them, he decided to include them in the auction.

“We think that we know what it’s like to be in prison because we watch movies and we watch TV,” Baca said. “But [through these letters] I think you really get an understanding of the mundane things, the grind on a daily basis, and what it’s truly like to be in prison.”

Baca said the auction house had expected to get between $400 and $700 for the letters, but that they ended up selling for between $1,300 and $1,500.

In addition to his displeasure with Boston’s changing demographics, Bulger also wrote about topics like the weather and the grub offered at the US penitentiary in Coleman, Florida.

“Food here is good, 2nd best in my years of eating prison food,” Bulger wrote in another letter.

Because federal law prohibits inmates from corresponding with each other through letters, Bulger’s letters are addressed to Ray Gallagher, who Glass said is a friend of his. Glass said Gallagher facilitated the correspondence between the two.

Glass said he got to know Bulger while he was detained at the Metropolitan Detention Center in Brooklyn, New York, from 2010-2014 after being charged with robbery. CNN was able to confirm that Glass was being held in the facility through records provided by Urban Culture Auctions and through Glass’ former attorney.

Bulger was transferred to the facility for a period of time in 2013, and Glass said the two formed a close bond during the time that they overlapped.

“Partly because I’m Irish too and just the criminal life,” Glass said. “We bonded, and he trusted me. And I had a lot of power in there at the time.”

Glass said he was surprised at how brazenly Bulger would talk to him about his criminal activities. He said the mob boss would ask him to take walks with him when they were both alone in the unit and Bulger would offer up gruesome details.

According to Glass, Bulger would talk about bunkers he had built, where he would keep his weapons, how he got rid of bodies and how he dug holes ahead of time.

“I’ve seen a lot of stuff in my life, but he was the real deal,” Glass said. “He was a stone-cold killer.”

Bulger was a ruthless kingpin of a criminal empire through his leadership of Boston’s Winter Hill Gang. He was a fixture on the FBI’s Most Wanted List, and evaded police for 16 years before being captured in 2011. He was found guilty of racketeering and involvement in 11 murders.

Bulger was also the inspiration for Jack Nicholson’s character in the Martin Scorsese film “The Departed.”

He was killed in a West Virginia prison last year at 89, while serving two life sentences and five years.