After Cus died, everybody around him was there to be with Iron Mike. None cared about Mike Tyson. He was a machine, but like any machine, a poor operator will yield poor results. Put Angelo Dundee as his handler, prison never happens. Holyfield gets destroyed. Buster Douglas is just another tin can.
$100 mil may be low. There were 3 years of missed fights that would have been in his prime. The fiasco against Douglas showed everything that was wrong with his trainers. They didn't push him hard in training, and, worse, during the fight, he didn't use the Peek a Boo style that got him there, rather, he stood around looking to one punch Douglas. Those boobs did away with his speed and defense, and didn't even pack an endswell for the fight, so his eye swelled shut way earlier than it should have.