Interestingly, Trump’s public behavior so far fits both of these theories.
For example, his attacks on vote by mail could be an attempt to suppress Democratic voters, an effort to preemptively establish a post-election challenge to results, or the groundwork for luring aggrieved Republicans to Trump TV, or whatever operation he stands up after leaving the White House. It could be either. Or both.
So no, I don’t claim to know what he’s thinking. And yes, he could come back and win outright. He could keep it close enough that electoral shenanigans make the difference, or at least so that the Republican party puts its institutional support behind post-election legal challenges. And even if he doesn’t pull any of this off, he might currently believe he can, and act accordingly.
But there’s also the possibility Trump thinks his presidency is ending and is running his old bankruptcy play, projecting confidence while anticipating a loss — a loss that he won’t let land on him.