So, on the one hand, nobody with Trump's current negative poll numbers has ever been re-elected.
On the other, who knows what will happen between now and 2020, again assuming he's also still in office.
On the third, just remember that a lot of things that were unprecedented have already happened with Trump. Here's one. Nobody with close to zero newspaper endorsements ever got elected.
But Trump did.
Ya know, I suspect Oliver's motive is a good one. One thing everybody fell for, myself included, in 2016, was complacency. Nate Silver said she had it in the bag! That Wang guy would eat a bug if he won!
Well he did (and look, for now, we'll put aside election manipulation questions) and Wang ate his bug. We can't get complacent. We never have anything "in the bag". Every voter who says "well, why bother to vote, she's got it in the bag," well the problem is, they are part of the bag.
You can't win if you don't assume it's always a struggle, assume it's a struggle, the reality is it often is.