Today, JFK Would be a Conservative

JFK would not by interested in conservativism as it stands today, having himself been subjected to the "everyone we don't like must be a Communist" attitude during his own presidency. He was even shot for it. I can't imagine he'd ever wear the red hat.

And he cheated too.

...on his marriage?

If you're talking about the election, it was his opponent who went on to become the closest any President has come to being charged with electoral shenanigans.