Trump doesn't have the mindset for a short seller. Shorts only come out when the stock market is dropping, and the last thing that Trump wants right now would be for the stock market to be doing what it's doing at the moment - shredding longs on it's way back to 20,000. He presided over a 12,000 point rise in the market, the largest ever in absolute terms (in relative terms, Obama's was still about 60% higher, even if you don't assume that the first year of a new administration is basically momentum from the last administration.
If you start Trump's "control" of the stock market from Jan 26, 2018 (when it hit a local maximum of 26,667) stocks have been anemic - up a maximum of 12% (earlier this year) and down about 15%. He's also now presided over two market drops in excess of 4,000 points consecutively, and had he not given corporations a tax vacation to bring back foreign assets, laundered through stock buybacks, it's highly unlikely that the DJIA would have he lofty heights it did.
Black swans do not cause markets to end. They simply expose when markets are too heavily overbought, and that exposure is what ultimately causes markets to fall. I think DJIA 20K may be a stretch, but I wouldn't be surprised if we revisit 22K. The market simply has not added that much value since Trump came to power.