Great timeline! Although why no ticket with Speaker Justin Amash and Prime Minister Boris Johnson?
I've often thought of doing something like this in President Forever, although it would take some time.
Of course, a party that puts the PM of Israel of all places on the ticket is obviously pretty pisspoor at strategy.
I would've had Matteo Renzi as Hillary's running-mate.
While I like the concept, I have problems with the plausibility of first, Hillary getting elected president and Libertarian Republicans (of which I happen to be) supporting repealing the Electoral College.
I'd support repeal, or at least major reform, of the Electoral College. It's a silly system. How can it be that the vote is 49.0% to 48.9%, but the person with 0.1% more gets 100% of the votes? It's irrepresentative. I'm libertarian because I think power comes from the individual, not the government, so I'd want to give the individual more power by making a more proportional voting system.
States like Texas and California would theoretically love it, because it would mean that candidates have to campaign there, and votes matter. However, Republican-controlled legislatures would never vote away their party's guaranteed EVs in favor of a more proportional, representative system (likewise for Democrat-controlled legislatures), and swing states would never vote away their influence on the final total.
My issue with this timeline is more with the Republican party. They nominate McCain, an establishment-hand-picked moderate, and he loses. They nominate Romney, an establishment-hand-picked moderate, and he loses. Then, in this timeline, they nominate Jeb, an establishment-hand-picked moderate, and he loses. If the party is still around by that point in 2020, they would
not nominate Chris Christie.
But both of those issues are peripheral in this timeline, so it's silly to talk about.