Description:

"Whitey" Bulger 3x Signed ALS Referring to Winter Hill Gang, Irish Gang War, & 21st C. War on Drugs

A small archive of items relating to James "Whitey" Bulger (1929-2018), the notorious Boston gangster, including a 3x signed autograph letter and original transmittal envelope; and two modern photo reprints of Bulger's mugshots taken in Boston and Alcatraz.

The lot is comprised of:

1. A 2pp autograph letter signed by Bulger at the letter's conclusion, as "James Bulger AZ1428AZ," (Bulger's U.S. Penitentiary at Alcatraz prison identification number). Also signed within the text as "Whitey" on the second page, with Bulger referring to himself in the third person. The letter was written in the high-security federal prison complex Coleman II located near Sumterville, Florida on August 26, 2016. Bulger wrote on either side of the blue-lined notebook paper, and along the side margin of the second page. Three-hole punched along the side. Expected paper folds and a few wrinkles, else crisp and clean. 8.25" x 10.375."

Bulger wrote this friendly letter to a Maryland man from his jail cell at Coleman II, the third prison before his last, a West Virginia lock-up, where Bulger was fatally bludgeoned to death in his wheelchair at age 89 on October 30, 2018. In the letter, Bulger refers to his own criminal history and his time as a fugitive and weighs in on such twenty-first-century social developments as the legalization of marijuana, the opioid crisis, and ineffective policing.

Bulger's letter is chock-full with interesting references to his criminal history. Bulger recalled: "I do have many pleasant memories of my time on the Rock. And did return as a tourist - like you - being on the Run had to go with the flow of tourists." Elsewhere, Bulger asks his correspondent, "What was your major - I graduated from the finest Crime college Atlanta - Alcatraz and Leavenworth Kansas - My Major was Crime - Earl Stanley Gardner wrote Criminals don't go to prison they come out of Prison - Read Oscar Wilde - Ballad of Reading Gaol - he said it all and still applys [sic]…"

Bulger served his first stint in federal prison at Atlanta Penitentiary, from 1956-1959, later transferring to Alcatraz, where he was imprisoned between November 1959 and July 1962. Alcatraz was not his first prison term, nor of a particularly long duration, but Bulger recalled his time there as special. From there, Bulger continued onto Leavenworth.

In the letter, Bulger explains why he avoided a local Irish pub in Santa Monica, California for fear of meeting other Bostonians, mentioning the Irish Gang War of 1961-1976. This tumultuous period of rampant gang revenge killings resulted in the estimated deaths of 60 people, and victims were assassinated while driving on public roads or waiting for the bus. Bulger refers to two members of the McLaughlin Gang, rivals of his own gang, the Winter Hill Gang: Stevie Hughes (ca. 1927-1966) and Connie Hughes (ca. 1930-1966). The brothers were gunned down five months apart.

Bulger writes conversationally about the Santa Monica, California neighborhood where he successfully eluded detection for at least 15 years, from 1994 to 2011. He describes a local bar, Sonny McLean's Irish Pub, and says that he got along well with Russian Jews in the neighborhood. He describes eating fish and chips at a tavern with his common-law spouse, Catherine Greig (born 1951), and a kind neighbor with a black long-haired chihuahua. The banality of Bulger's comments about being "on the Run" belies the constant danger he was in while a fugitive.

Bulger's perspective on the twenty-first-century war on drugs is especially interesting. "Things have changed in prison brought on by the drug craze that seems to have swept America - for the Worst and some P.C. moron feels the Solution - Make Marijuana Legal -," Bulger wrote derisively. Despite his own past involvement in drug distribution while head of the Winter Hill Gang from 1979-1994, Bulger presents himself as stolidly anti-drug. He praises the anti-drug policies of President of the Philippines Rodrigo Duterte, even comparing himself to Duterte. Bulger explained that he alone controlled the "Heroin and Angel Dust" situation in his neighborhood and that after he went on the lamb, drug use there skyrocketed: "'If Whitey were here that wouldn't happen...'"

2. Its original transmittal envelope, fully engrossed in Bulger's hand, and signed by him a second time in the return address section, as "James Bulger 02182748," (Bulger's U.S. Penitentiary at Coleman II prison identification number.) The envelope bears a cancelled stamp and was postmarked from Tampa / St. Petersburg, Florida. Neatly letter-opened at top.

3. Two modern photo reprints of Bulger's mugshots, including his mugshot in Boston on March 16, 1953; and his mugshot taken at Alcatraz on November 16, 1959. The smaller photo printed on Fujifilm photo paper measures 5.875" x 4." The larger satin-finish photo measures 10" x 8." Near fine.

This item comes with a Certificate from John Reznikoff, a premier authenticator for both major 3rd party authentication services, PSA and JSA (James Spence Authentications), as well as numerous auction houses.

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March 30, 2022 10:30 AM EDT
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