Is the Popular Vote unwinnable for the GOP?

[Tartarus Sauce]

It depends on which path they decide to choose as a party post-Trump. Double down on Trump's strategy? Not only will they never win the popular vote, they probably won't even crack 45% again. Run a more palatable candidate against a really bad Democratic candidate? Certainly, I'm just not sure such a candidate could survive the GOP primaries nowadays.

[Tartarus Sauce]

I think we are overlooking that Trump is from NY and NY has a strong pro-incumbent tendency to boot.  If the 2020 Dem doesn't also have NY ties like Clinton did, the state could trend pretty hard to Trump.  Trump only losing NY by say 12% in a close 2020 election vs. 22% in 2016 would be a game changer in terms of the PV.

The last time we've had a Republican incumbent president run is 2004 and Bush got blown out by 18 points. All things considered, there doesn't seem to have been any advantage for Republicans.

I don't think Trump is going to come close to those numbers in New York. They don't seem to like him, going by his approvals.

If anything, he'll probably do worse, since the city will hate him just as much and upstate will have likely soured on him quite a bit by 2020. I'm not sure what makes him think he has any realistic chance of narrowing down his margins to 12%.