AHC: President Jesse Ventura:

Your challenge, should you accept, is to make Jesse Ventura, former wrestler and former Minnesota Governor, President of the United States. My guess is that 2004 or 2008 would be the easiest elections to make it happen.
 
The problem is that Jesse Ventura was able to get elected in Minnesota because the state has strict campaign finance laws meaning the Democrats and Republicans could not bury him with money. In a national election, he gets buried with money.
 
You're going to have POD right after the election and change his personality to make him less combative with both the state DFL and GOP, as well as the press. He didn't make much of an effort to really work with either party, and just kind of antagonized leaders from both sides instead of any efforts at coalition building. As his term went on, there were fewer and fewer people willing to work with him, and no consequence for their reluctance. Plus, his relationship with the press was downright toxic and juvenile (printing 'Media Jackals' on press passes, blaming the press when his son's friends trashed the Governor's mansion). By 2002, it was pretty clear he would not have won a second term.
 
I dunno if I'm up for the challenge, but I have a nomination for the thread title: Win If You Can, Lose If You Must, But Always Cheat: The Jesse "The President" Ventura Story
 
Given his similarity to Trump (and even Sanders to a degree), both in terms of rhetoric and style, I think he'd probably have a shot in an alt-2016.

Maybe if Trump doesn't run and the GOP instead nominates some unpopular establishment figure (maybe Jeb Bush). I could see Ventura managing to run a popular populist campaign that could give him a shot.
 
Have Ventura run as a populist independent who has his campaign bankrolled by Donald Trump. Trump could start off by saying, "Hey, I have no interest in elected office, I would need to watch my mouth too much but I think my friend Jesse would make a great president and that is why I am proud to do whatever it takes to make it happen."
 
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