Dale Earnhardt, Jr. – $400 Million

When racing champion Dale Earnhardt, Jr. drove his last NASCAR race at the 2017 Ford EcoBoost 400 in Homestead, Florida, a lot of fans were very emotional. Many remembered the first time he drove in a NASCAR race in 1988. His professional life saw at least 50 victories, and he’s considered one of the richest athletes of all time. Today, his net worth is now at $400M. During the prime of his career, his endorsement deals paid him up to $23 million in a year. Following his NASCAR retirement, he continued to race in series like the Sprint Cup. He started his stint as a NASCAR announcer on NBC Sports in 2018.