I keep thinking about the electoral college, and how slim Trump's win was in 2016.
He won Michigan by 10,704 votes, Pennsylvania by 44,292 votes, and Wisconsin by 22,748 votes.
If half-plus-one of those voters in each of those states had gone Clinton, Trump wouldn't be president.
So when Trump does something like, say, go to Michigan and make a
joke about how a popular, recently-deceased Michigan politician is in hell? Stuff like that could, honest to God, decide the 2020 election.
Trump got booed at his own rally. Think about what that means. Yes, every last one of those motherfuckers booing him at his rally is going to vote for him anyway -- they're at a Trump rally, for God's sake -- but outside that rally? Is it possible that there are maybe 5400 voters in Michigan who went Trump last time but might go Democratic next time over a remark like that? Yeah, it's possible.
Obviously it's a lot more complicated than that; 2020 isn't going to be exactly the same voters voting in exactly the same way. And there are other factors that favor Trump -- religious voters who were wary of him in 2016 (yes, there were some; remember McMullin getting 22% of the vote in Utah) have largely come around to supporting him, whereas people who were wary of the effect Trump might have on the economy seem like they're convinced now that he's doing a good job. (That could, of course, change in the next ten months.) I think 2020 is going to be close -- it would be nice if it weren't, it would be nice if it were a thorough repudiation of him, but I don't think that's something we can count on.
But in a close election, any stupid thing Trump does could swing it.
The bad news is, well, we saw what happened in 2016; the media spent the entire race drawing false equivalence between Clinton's mistakes and Trump's. We've got plenty more of
that to look forward to.