A photograph of JFK taken for a blackmail attempt will cross the block at RR Auction on November 9.
It shows Kennedy leaving the home of his secretary, Pamela Turnure, on the night of July 11, 1958.
It's attached to an anonymous letter dated May 27, 1959, which was sent out to various journalists.
This example is addressed to Stuart Symington, Kennedy's rival for the presidential nomination.
It transpired that the letter had been sent by Turnure's landlords, Florence and Laurence Kater.
They tried to blackmail Kennedy and his staff into giving them a Modigliani painting in exchange for their silence, but when they were rebuffed they went to the press.
The letter reads: "Here is Senator John F. Kennedy of Massachusetts, hand hiding his face, recently snapped when leaving his girlfriend's place at 1 o'clock in the morning.
"She is a 'glamour type' employee of his. That's a handkerchief in the senator's right hand. In fact, everything's there to see but a touch of greatness�Ǫ
"We are sending this to you without the knowledge of the people involved because we feel that their lofty approach���sticking only to the job-threat angle���did not show the crumminess of Senator John F. Kennedy, the man who hopes to become the next President of the United States."
Unfortunately for the Katers, none of the papers took up the story as the image did not show Kennedy's face or prove he was having an affair.
Kennedy and Turnure are believed to have had a long running affair, which continued during his presidential term. She would be hired as Jackie Kennedy's press secretary in 1961.
The lot is valued in excess of $15,000.
We have this original poster from Kennedy's 1960 presidential campaign for sale.
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