Bizwah
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The Kennedy Presidency is a real bugger to judge. On one hand he and the Jackie were mesmerizing. There's just no two ways about it... Like'em, dislike'em you have to say he (they) were more charismatic than any president/first lady since then.
The showdown with the Soviet Union... I don't think any of us who didn't go through that can really understand the tension brought to the entire country and world over that situation. And Kennedy handled it about as well as you could.
For me that's the high point of his presidency. You've got a boatload of outright failures like "Bay of Pigs" and of course there is a connection to Vietnam (no matter what he would have done about Vietnam if he had lived).
I've read that there were no major legislative pieces put forth by the Kennedy administration during his time in office... which of course would be a negative.
He is tough to evaluate. He did very well during the Cuba Missle Crisis. He ignored the unanimous opinion of the Joint Chiefs (who wanted an invasion ), and kept his head. Yet, it was his bungling the Summit with Soviet Premiere Kruschev, that caused the Soviets to try planting missiles in the first place.