More Words, Deeper Hole

No, Khrushchev didn't know how reckless he was being. He figured, based upon Kennedy's bungling of the Bay of Pigs and Vienna Summit, and weak response to the Berlin Crisis, that JFK would roll over once again, especially since any strong objection to the Cuban missiles would by hypocritical in light of the Turkish IRBMs. Unfortunately Kennedy was a hypocrite (or at least his military advisers were) and pushed the world to the brink of war because the Soviets had done to the US what the US had already done to the Soviets.