Michael Jordan

He didn't want Nike. He was an Adidas guy and had to be talked into taking the meeting. Nike offered $500,000 a year plus a signature shoe, and the Air Jordans moved over $100 million in their first year. The following season's playoffs included a 63-point game that made Larry Bird call him 'God disguised as Michael Jordan.' He went on to win six championships in eight years. The sneaker money eventually lapped the basketball money by a wide margin.

He sold his majority stake in the Charlotte Hornets in 2023 at a $3 billion valuation, having paid $275 million for control in 2010. The real money has always been the shoe. Jordan Brand pulls roughly $7.3 billion a year for Nike, and his estimated 5% royalty reportedly puts him around $150 million annually, more than he ever made in basketball. He's co-owning 23XI Racing and took NASCAR to federal court in an antitrust case that settled in late 2025. The guy who once got fined by the NBA for wearing red-and-black shoes is now taking a sports league to court.

The part most people skip over is his brother Larry. Larry Jordan was 5'8" and never made it to the NBA, but Jordan has said he would've been 'Larry's brother' his entire career had Larry been taller. His father James was murdered in a carjacking in July 1993, two months before Jordan announced his first retirement. The baseball detour wasn't a breakdown. He's said his father had always wanted him to play both sports, and playing minor league ball was keeping that conversation alive. His manager Terry Francona reportedly believed Jordan could have reached the majors.