Mike Tyson
Iron Mike was knocking out people left in the mid-80s to mid-90s. However, after a string of arrests and debts that accumulated to tens of millions, Mike Tyson was pretty much gone from the spotlight. Even when he wasn’t doing interviews and delivering speeches, he still had a comfortable pile of money to live on, so it’s not like he was ever broke.
In late-2020, Mike Tyson came back into the boxing ring after several decades of inactivity. In his fight against Roy Jones, Jr., he pocketed a cool $10 million while his opponent just got $3 million for his troubles. The fight ended in a draw, which Mike Tyson felt was deserved.