Mike Tyson became the youngest heavyweight champion in history at 20 years old in 1986, and over the course of his career earned an estimated $400 million or more from fights alone — including a reported $30 million purse for the infamous 1997 rematch against Evander Holyfield, the one that ended with Tyson biting off part of Holyfield's ear.
The money funded a lifestyle built for spectacle: multiple mansions across several states, a fleet of luxury cars, a jewelry collection, and a pair of white Bengal tigers he kept as pets, reportedly costing well over $100,000 a year just to feed and house.
A 1992 rape conviction sent Tyson to prison for three years, interrupting his career at its peak and cutting off the income stream that had been funding an already-enormous entourage — bodyguards, assistants, and hangers-on, many kept on payroll even when Tyson wasn't fighting.
Divorces, lawsuits, and a bitter legal war with longtime promoter Don King — whom Tyson later sued, claiming he'd been swindled out of more than $100 million over the years — chipped away at what remained. Expensive advisors and an entourage that never shrank meant the overhead kept running long after the paydays slowed down.
Tyson filed for Chapter 11 bankruptcy in 2003, listing around $23 million in debts against what he estimated were nearly $400 million in career earnings — essentially all of it gone.
He rebuilt gradually in the years after: a one-man Broadway show, a documentary about his own life, a memorable cameo in The Hangover, and eventually a cannabis business — one of the few cases in this archive where the story didn't end at rock bottom.
Ad space