Whitey Bulger prison letters steal the show

The prison correspondence of Boston gangster Whitey Bulger Jr. stole the spotlight at Urban Culture Auctions’ (UCA) Feb. 24 debut auction.
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WEST PALM BEACH, Fla. – Every auction has its surprises; the prison correspondence of Boston gangster Whitey Bulger Jr. stole the spotlight at Urban Culture Auctions’ (UCA) Feb. 24 debut.

2015 holiday card sent by gangster Whitey Bulger featuring his 1959 Alcatraz mugshot and a cordial seasonal greeting. Sold together with a handwritten letter for $1,430.

2015 holiday card sent by gangster Whitey Bulger featuring his 1959 Alcatraz mugshot and a cordial seasonal greeting. Sold together with a handwritten letter for $1,430. Photos courtesy of Urban Culture Auctions

The 289-lot Sunday session that piggybacked a modern design sale hosted by UCA’s parent company, Palm Beach Modern Auctions, featured a mix of what auctioneer Rico Baca called “the fun stuff – from iconic pop furniture and graffiti art to street fashion, celebrity memorabilia and Space Age electronics.”

The Bulger items drew widespread interest. Whitey Bulger died at the hands of fellow prisoners within hours of his arrival at a U.S. penitentiary in West Virginia in October 2018.

Prior to that time he had maintained a correspondence from behind bars with Timothy Glass, a one-time prisoner he met years earlier while incarcerated at the Metropolitan Detention Center in Brooklyn, New York.

St. Patrick’s Day 2015 notecard and handwritten letter sent by Boston gangster Whitey Bulger from behind bars, $1,430. Photos courtesy of Urban Culture Auctions

St. Patrick’s Day 2015 notecard and handwritten letter sent by Boston gangster Whitey Bulger from behind bars, $1,430.

Glass saved all of the handwritten letters, cards, mugshots and other ephemera he received from Bulger, which, as a whole, painted a picture of an elderly criminal who found it difficult to adjust to today’s prison culture.

In his written recollections, Whitey Bulger longed for the “good old days” at Alcatraz.

He even chose to use his 1959 Alcatraz mugshot on a 2015 holiday photo card that carried the greeting “Wishing You Peace & Cheer in the New Year.” The card sold together with a handwritten letter for $1,430.

The same price was achieved by a letter and St. Patrick’s Day note card with the image of a South Boston fence painted with Irish iconography.

Additional auction highlights

Additional interest is found in mid-century electronics, which attracted many enquiries, Baca said. The top lot of the group was a Weltron GEC-2005 stereo system with a “Jetsonesque” look. Supported on a pedestal, the all-in-one system included a turntable, AM/FM stereo radio, 8-track player and both internal speakers and external auxiliary ports ($7,800).

Cast-iron three-dimensional figure of Michelin Tires mascot ‘Bibendum,’ $2,080.

Cast-iron three-dimensional figure of Michelin Tires mascot ‘Bibendum,’ $2,080.

Younger collectors responded enthusiastically to a selection of Haitian naïve art, with all but one of the 23 offered lots finding new owners.

An unusual advertising piece, a nearly 2-foot tall cast-iron figure of the Michelin Tires mascot “Bibendum” sold for $2,080.

A Vladimir Kagan “Serpentine” sofa in deep royal blue topped its estimate range with a winning bid of $16,900. Mid-century art put in a strong performance, as well. A small 1971 acrylic-on-wood artwork by Ilya Bolotowsky titled Miniature Yellow Tondo, artist-signed and measuring 7¾ inches in diameter, sold for $9,100.

To learn more, contact 561-586-5500 or uca@modernauctions.com, or visit https://urbancultureauctions.com/

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