A reputation for hurting someone for tens of thousands of dollars is like saying "hey, please don't do this" in advance to everyone who hears about it.

Maisel is in the comfortable position where he doesn't need to do that anymore and hasn't needed to for a long time. That is why this was wrong of him. He doesn't need to protect his reputation or commercial interests against some tiny project doing an 8-bit tribute to Miles Davis. He gains nothing: the net effect is that this guy, that tried to do something nice that made a few people happy, get slapped. Nothing else has come of this lawsuit.

People will continue to not fuck with him or his estate. You don't get rich by writing a lot of checks.