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Lot #3040
John Dillinger Autograph Letter Signed from Prison

Incredibly rare handwritten Dillinger letter relating to the infamous ‘Shirt Shop Boys’

Estimate: $15000+
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Incredibly rare handwritten Dillinger letter relating to the infamous ‘Shirt Shop Boys’

ALS in pencil, signed "John Dillinger #14395," one page, 7.75 x 3.75, no date [but circa 1929-1933]. Handwritten letter from Indiana State Prison at Michigan City, sent to prison assistant superintendent H. W. Waymire, in full: “I am working in the shirt shop and the work is hard on my eyes and I would like to get transferred to the foundry #4 or Machine shop if possible. I will certainly appreciate it very much if you will do what you can for me." Double-matted with a typed prison memo marked “See Dr.,” stating that “14395…Dillinger…Wants a transfer to the foundry from the shirt shop says the shirt shop is hard on his eyes,” a scarce original 1934 US Justice Department wanted poster with mugshot and fingerprints, and a glossy portrait of Dillinger holding a pistol and a Tommy gun, all of which are framed together to an overall size of 28.75 x 14.5. In fine condition, with light creasing, and file holes and staple holes to the top edge.

In 1924, Dillinger was sentenced to 10-20 years for his part in the assault and attempted robbery of a grocery store owner in Mooresville, Indiana. While working in the shirt shop at Indiana State Prison, he befriended the men who would later become his notorious ‘Shirt Shop Boys,’ a group that included Handsome Harry Pierpont, Charles Makley, and John Hamilton. The men spent hours devising elaborate escape plans and foolproof crimes, and upon his parole in 1933, Dillinger put their various schemes to action, robbing his first bank on June 21st. Dillinger was arrested for another robbery two months later, but before his capture he had successfully smuggled guns into the cells of his former ‘Shirt Shop Boys,’ which they promptly used to escape. On October 12, those same men, disguised as Indiana State Police officers, freed Dillinger from his own cell, killing a sheriff in the process. Dillinger remains exceedingly rare across all formats, with this example representing the only letter we have ever offered.

Auction Info

  • Auction Title: Remarkable Rarities
  • Dates: #638 - Ended June 23, 2022

This item is Pre-Certified by PSA/DNA
Buy a third-party letter of authenticity for $500.00

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