Kennedy did some good things, but he was a major asshole in plenty of ways. The Bay of Pigs invasion was both stupid and a disaster, he escalated things in Vietnam, he put a huge stall on civil rights while claiming to be championing it to the point that Lyndon fucking Johnson had to do something about it, and then there were those 13 days in October, 1962 where he almost helped end the world. And that all started when he decided to deploy nuclear weapons in Turkey.

So I wouldn't even include him in the 'not an asshole' category.