Trump has been doing this fraud-in-plain-sight thing forever.
I've read comments that say it works because the defense is that it's so obvious it can't be deceitful. As in: if you wanted to hand $15m to a donor you'd find a secretive way to do it.
I personally believe it's just learned ineptitude. He's just deceitful at every turn and he's never encountered any consequences so why would he change?