He would have won in a walk in 2008. Obama would have been his VP likely.
How would he have done? A sight better than Obama as he seemed like a pretty level-headed guy in terms of politics somewhat. We are talking late 90s Democrat, btw.
The downside is that Obama would be in his first term today.
... or JFK Jr. would have been our Justin Trudeau. The father was tested in combat and was well educated with some exposure to international diplomacy thru his father. Jr. was a journalist.