Terrell Owens

Terrell Owens earned approximately $80 million in NFL salary over 15 seasons and was one of the most talented and entertaining wide receivers in football history. He ranks third all-time in receiving yards and receiving touchdowns, and his touchdown celebrations -- including the Sharpie signing, the Dallas star stomp, and the popcorn eating -- made him one of the most must-watch athletes of his era. He was inducted into the Pro Football Hall of Fame in 2018.

Owens's story is the starkest cautionary tale in this entire ranking. Despite earning $80 million in salary plus endorsement income, he has publicly acknowledged being nearly broke. Bad real estate investments, trusting the wrong financial advisors, expensive divorces and child support obligations, and a lifestyle that exceeded even his considerable income systematically destroyed his wealth. By some estimates, he spent $50,000 per month on lifestyle expenses during and after his career.

Owens has attempted comebacks through Fan Controlled Football, the Indoor Football League, and has appeared on reality television shows including The Masked Singer and Dancing with the Stars. His Hall of Fame speech -- delivered at his home in Chattanooga, Tennessee rather than in Canton, Ohio -- was a final act of defiance that encapsulated his career: supremely talented, stubbornly independent, and financially tragic.