The ultimate October surprise
By 
As a semi-officially certified (ABD) Trumpologist, I’m offering this up because, while I think this outcome is unlikely, I don’t think it’s highly improbable. If you gave me 10-1 odds on it I would probably take that.
How this could happen is very easy to game out. Suppose Harris’s current momentum continues to build through the convention and into the fall. Trump’s current wild flailing about how she isn’t really black, which is the Greta Van Fleet of Stairway to Birtherism, is, I believe, evidence of quite a bit of incipient panic.
The Ariana Grande voters really did not want to have to choose between Joe Biden and Donald Trump. Yes they are complete idiots, but you campaign with the electorate you have, not the one you would like to have. Now:
(a) The swing/squish/more confused than Nigel Tufnel voters have an alternative; and
(b) The Democratic base is energized and enthusiastic and motivated at levels we haven’t seen for a long time.
It’s far from improbable that the Trump campaign could be in dire straits by the middle of the fall. To be clear, I’m not saying this series of fortunate events will happen; I’m saying that it’s quite plausible to see something along these lines happening, without mainlining too much hopium or engaging in pure wishcasting.
If this does happen — If say Trump is down by seven points nationally and looking real bad in most of the swing states on, say, October 4th — can I see him just up and quitting? I can absolutely see that happening. Trump doesn’t handle public humiliation well under the best of circumstances, and getting publicly humiliated by a black woman is, for him, pretty much the opposite of the best of circumstances.
Again, I think this is an unlikely outcome to our current wild ride through historical contingency (imagine if the first debate had been in early October, as has always been the tradition), but I don’t think it’s a wildly improbable one by any means.
Among other things, such a complete betrayal of his most loyal supporters at the worst possible moment would be an almost-too fitting conclusion to the strangest career in the history of American politics. But I think it’s fair to say that one thing the twists and turns in our little saga have lacked up to this point is anything like metaphorical subtlety.
Tan Ciera, tan Ciera!