An alternate universe in which:
2000: Bush defeats Gore
2004: Bush defeats Kerry
2008: Clinton defeats McCain (Obama loses Iowa Caucus, is reelected to the Senate in 2010 and 2016)
2012: Clinton defeats Romney
2016: Trump defeats Clinton's VP Evan Bayh
And then start the timeline with:
2020: Trump vs. Obama
If that's not a new progressive era for America, then I don't know what is. A left-wing NUT timeline for sure, but if we're going to be an echo chamber here, we might as well commit to it.
There is no way that Donald Trump runs as a Republican in 2016 if Hillary Clinton was elected in 2008.
It's a timeline. Take some creative liberties.