From “The Very Best Men” – Four Who Dared: The Early Years of the CIA "
by Evan Thomas (Simon & Schuster, 1995) p. 303
“…(Sam) Halpern, FitzGerald’s assistant, regarded (Cubela) him as an assassin and claims that FitzGerald did as well.”
Sam Halpern: “Des was really more interested in starting a coup, and he hoped that Cubela could organize other army officers. But in coups, he understood, people die. The way to start a coup is to knock off the top man. Des felt it was a long shot, but it might work. We were desperate. Des was willing to try anything.” 35 –
Thomas: “FitzGerald did not think it was such a long shot that he was unwilling to make a small bet, giving reasonable odds. Just six days before he formally signed off on a high-powered rifle for AMLASH (Cubela), he accepted a little wager from Michael Forrestal, an official on the National Security Council staff who was a member of the Georgetown crowd (his father, James V. Forrestal, had been the first secretary of defense).
A memo in FitzGerald’s personal files records a $50 bet with Forrestal on ‘the fate of Fidel Castro during the period 1 August 1964 and 1 October 1964. (Apparently, Fitzgerald saw a window of vulnerability for the Cuban leader that was roughly coincidental with the 1964 U.S. presidential election campaign.)”
“Mr. Forrestal offers two-to-one odds ($100 to $50) against Fidel’s falling (or being pushed) between the dates 1 August and 1 October 19645. In the event that such a thing should occur prior to 1 August 1964 the wager herein cancelled. Mr. FitzGerald accepts the wager on the above terms.”
Memo is dated November 13, 1963. “One day after FitzGerald briefed Kennedy on the progress of the Cuban operation and one day before the Special Group approved his plan of continued covert operations against the Castro Regime.”
Thomas: “Nine days later the assassination of John F. Kennedy dramatically increased the odds that FitzGerald would lose his bet.”