WI: Donald Trump never won the 2016 election but a dark horse candidate won.

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Perhaps Rand Paul was different enough to really be divisive enough to many voters (his foreign policy mostly.) I imagine the media would attack him relentlessly, but he's jsut less interesting than Trump--you would not be getting as much as the Russia stuff.
 
A darke horse candidate? How much more dark horse then Trump can you get. I mean he did try out more as a media stunt then for real to get on the ballot in 2012, but apart of that, until a month before the primaries he was just a reality TV star with lots of money. Even until spring of 2016 he was the odd man out amongst all the Republican candidates.

At a guess, a dark horse would not be someone who's been flitting around the edges of the political arena for 30 years, whose talents were recognized by Richard Nixon, and who polled extremely well from the moment they entered the race.
 
Was she qualified age wise? She would be a few months short of 35 year old during the inauguration.

No. I was going to point this out, but you beat me to it. This kills the scenario completely in my mind. There aren't many qualifications in the Constitution for being President, but being 35 is one of them.
 
Well, since Danielle Wilson sounds made up, we can as well pretend she was born in 1981 instead.

With a billionaire backing her campaign and several well-connected politicians in her team and a talented election campaign management, I think the best performance she could pull off would probably be something like Ross Perot in 1992. But you'd need a scenario where both Democratcs and Republicans have been going morally and politically bankrupt, i.e. a Watergate-esque thing happening in both parties. Given those kind of circumstances, people might go for a candidate only involved in local politics (therefore having more actual experience in politics than OTL Trump) and therefore not being corrupted by "the system".

But in reality, Trump wasn't really a dark horse: he was well-known throughout the USA and beyond, he already dabbled with the GOP nomination in 2012, he was involved in the Reform Party, and despite having no experience in politics, he always was well connected to the political machinery. In certain ways, Bernie Sanders was more of a dark horse than Trump - and Fiorina and Carson on the GOP side as well.
 
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