Mike Tyson

Brownsville, Brooklyn in the late 1970s produced 38 arrests for him before age 13. A reform school counselor and former boxer named Bobby Stewart saw something worth saving and introduced him to Cus D'Amato, the trainer who'd built Floyd Patterson into a champion. D'Amato became his legal guardian after his mother died, taught him the peek-a-boo style, and shaped him into something terrifying. D'Amato died in November 1985. A year later, Tyson knocked out Trevor Berbick in two rounds and became the youngest heavyweight champion in history at 20 years old.

He lost to Jake Paul by decision in November 2024, but 108 million people watched it on Netflix, making it the most-streamed sporting event at the time. The cannabis play is where the real money is now. Tyson 2.0 reportedly pulls over $50 million a year, and the marquee product is Mike Bites, ear-shaped edibles that turn the 1997 Holyfield incident into a revenue stream.

The trainer died just over a year before Tyson took the title, and never got to see it. The mentor who might've kept him grounded was already gone when the money and the chaos arrived. Tyson has said D'Amato saved him from a violent early death in Brownsville. His 2017 memoir Iron Ambition spent more time on D'Amato than on himself, which is either a tribute or an admission that the best version of Tyson died with his trainer.