Crossposting from the Shaun King 2020 thread:
I feel like a lot of you guys lack a ton of common sense when discussing hypotheticals like these. It's not like people are randomly thrust into the Democratic nomination; if Shaun King Lena Dunham turned out to be so politically talented and so popular among the Democratic base that he was able to successfully sell herself to a plurality of Dem. primary voters, that alone will guarantee her at least 45% in the general election. As such, she'd easily receive 180+ EVs and could certainly end up doing much better than that.
As much as I hate Lena Dunham, in the Bizarro World that we live in, I'd feel much better about her chances in a GE than a generic "normie" politico like Vilsack; I could see her pushing millennial voters to turn out in droves comparable to Trump's affect on rural voters this cycle.
I am a millenial. I am a Progressive. I would vote for Trump.