JFK would pretty much be a republican nowadays.
There was a lot that Kennedy did that would be right of the establishment Republicans, but he did a lot that mirrored Obama: spying on opponents, weaponizing government agencies, wiretapping public figures... another highly flawed man.
On the subject of Kennedy’s man-whoring, which includes an underage East German spy, I recently heard LBJ slept around with a lot more women than Kennedy. And unrelated, but LBJ’s own historian said his Silver Star (Johnson served as a Naval officer during World War II) was the most undeserved Silver Star in military history.