Boston gangster Whitey Bulger’s prison letters, mugshots in Feb. 24 auction

Whitey Bulger

2015 holiday card sent by gangster Whitey Bulger featuring his 1959 Alcatraz mugshot and a cordial seasonal greeting. Together with handwritten letter, it is estimated at $400-$700

WEST PALM BEACH, Fla. – An archive of handwritten letters, cards, mugshots and other ephemera related to notorious Boston gangster James “Whitey” Bulger Jr. (1929-2018), will cross the auction block on Sunday, Feb. 24 in West Palm Beach, Florida.

The collection of personal correspondence has been consigned to Urban Culture Auctions by an associate of the late crime boss. The two met while they were incarcerated at the Metropolitan Detention Center, a Federal Bureau of Prisons facility in Brooklyn, New York. Both men were convicted of felonies and subsequently transferred to different prisons to serve their sentences, however they maintained a correspondence in the years to follow.

Although federal law prohibits mail communication between incarcerated felons, Bulger got around the issue by organizing a third party on the outside to receive his letters, place them in newly addressed envelopes and redirect them to his friend, who was serving time for first degree murder, armed robbery and impersonating an officer of the law.

Among the items in the archive is a 2015 holiday card featuring Bulger’s 1959 Alcatraz color mugshot and the greeting: “Wishing you Peace & Cheer in the New Year.” A St. Patrick’s Day notecard was also sent in 2015 and, like the holiday card, is accompanied by a handwritten letter. Both auction lots carry an estimate of $400-$700.

Whitey Bulger

St. Patrick’s Day 2015 notecard and handwritten letter sent by Whitey Bulger from behind bars. Auction estimate: $400-$700

Bulger, a ruthless career criminal and head of the so-called Winter Hill Gang, was indicted for 19 murders, however he fled Boston in 1994 before authorities could flush him out of hiding and arrest him. Bulger went on the lam and remained at large for 16 years. For 12 of those years, he was second only to Osama bin Laden on the FBI Ten Most Wanted Fugitives list.

In 2011, a tip led to Bulger’s whereabouts. He was arrested outside an apartment in Santa Monica, California, and extradited to Boston, where he was later tried on 32 counts of racketeering, money laundering, extortion, weapons charges, and complicity in the aforementioned 19 murders. Bulger was found guilty on 31 counts and sentenced to serve two consecutive life terms plus five years. In November 2013, he was sent to the US Penitentiary Coleman II in Sumterville, Florida.

Five years later Bulger was transferred to the Federal Transfer Center in Oklahoma, then to the US Penitentiary in Hazelton, West Virginia. Within hours of his arrival, Bulger, who was wheelchair-bound, was found dead, the victim of an attack by inmates.

“Whitey Bulger was a ruthless killer and died as violently as he lived, but he still holds a certain fascination with the public. His life and persona have served as the inspiration for at least a half dozen TV shows or crime characters,” said Rico Baca, auctioneer and co-owner of Palm Beach Modern Auctions, parent company of Urban Culture Auctions. “The letters he wrote to his friend from prison offer an intriguing look into his mind and what made him tick.”

The Sunday Feb. 24 auction will begin at 11 a.m., with absentee and Internet live bidding through LiveAuctioneers. For additional information call 561-586-5500 or email

By Catherine Saunders-Watson

Copyright 2019 Auction Central News International