I truly think it’s a phenomenal strategy on Trump’s part, though recognize that he could just be doing this to be a prick without any 4D chess at hand.
The media will, by and large, spend their time criticizing Trump no matter what. Would he rather they solely focus on “legitimate” grievances such as COVID-19/Russia/overstep of powers or, conversely, complain about Trump’s remarks regarding a relatively unknown death from 20 years ago? Conspiracy theories tend to be pretty dumb, but also serve as a nice little time waster and I’d much rather have people talking about/researching Joe Scarborough than something harmful towards Trump.
He needs to jump the shark and start dropping Chappaquiddick references to really drum up that media ire.