The first letter that was sent was believed to be written by Khrushchev himself, as CIA director John McCone explained, was done by someone "under a great deal of stress" and bypassed the Politburo who would have filtered it more thoroughly. However, as Kennedy and his group were considering accepting the terms of the first letter to end the standoff, a 2nd letter was submitted by the Soviets which more or less seemed to make the first letter a ploy to buy time.
Kennedy and a few others decided one last round of diplomacy was in order, with the plan being to totally disregard the 2nd letter, agree to the terms of the first (to never invade Cuba), and also agree to withdraw the Jupiter missles from Turkey, but the deal was off if the Russians made this public, and had only 24 hours to accept...which of course, they did, as we are all still here.
As far as the spy goes, it is unclear for sure if he was Khrushchev's friend, or "war buddy" as they said in the film. There again, another ploy by the Russians to buy time. John Scali believed the intent was genuine and it was worth a try.
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