Why They Rank
Three-time World Series champion with Boston. $159M in MLB salary. Broke the Curse of the Bambino. Nike, Dunkin', JetBlue endorsements. Fox Sports media career.
The Fortune
David 'Big Papi' Ortiz earned approximately $159 million in MLB salary over 20 seasons, the majority with the Boston Red Sox. He was the most clutch hitter in Red Sox history, leading the team to three World Series championships (2004, 2007, 2013) and earning World Series MVP honors in 2013. His role in breaking the 'Curse of the Bambino' in 2004 made him the most beloved figure in Boston sports history.
Ortiz's endorsement portfolio included Nike, JetBlue, Dunkin' Donuts, and MasterCard. His larger-than-life personality and infectious smile made him a natural pitchman, and his endorsement income at peak reached approximately $6 million per year. Post-retirement, he became a Fox Sports analyst and has maintained commercial visibility through media appearances and brand partnerships.
Ortiz was shot in a nightclub in the Dominican Republic in 2019, an event that generated worldwide concern. He survived and fully recovered, returning to his media career. His net worth of $75 million reflects a career that generated significant income in a major market, combined with the kind of personal brand that maintains value long after retirement.
Wealth Source
MLB salary, endorsements, media career, investments
Top Endorsements
Fun Facts
His 'This is our f***ing city' speech after the 2013 Boston Marathon bombing is one of the most iconic moments in Boston sports history.
He was signed by the Red Sox after being released by the Minnesota Twins for $1.25 million -- one of the greatest bargains in baseball history.
He survived being shot in the back in the Dominican Republic in 2019, making a full recovery that he called his 'biggest clutch moment.'
Frequently Asked Questions
Who is the richest athlete of all time?
Michael Jordan is the richest athlete of all time with an estimated net worth of $3.5 billion. His wealth comes primarily from the Jordan Brand, the sale of the Charlotte Hornets, and decades of endorsement deals. His NBA playing salary was just $94 million -- a fraction of his total fortune.
How do athletes build wealth beyond their playing salary?
The wealthiest athletes build wealth through endorsement deals, equity stakes in companies, brand ownership, franchise ownership, venture capital, and real estate. The key insight is taking equity over flat endorsement fees whenever possible -- turning short-term fame into long-term compounding assets.
Which athletes are billionaires?
As of 2026, four athletes have confirmed billionaire status: Michael Jordan ($3.5B), Tiger Woods ($1.3B), LeBron James ($1.2B), and Magic Johnson ($1.2B). Several others are approaching the threshold, including Arnold Palmer's estate ($875M), Lionel Messi ($650M), and Michael Schumacher ($600M).
Get Glen’s Updates
Investing insights, new tools, and whatever I’m building this week. Free. No spam.
Unsubscribe anytime. I respect your inbox more than Congress respects property rights.
Keep Exploring
Top 25 Richest Athletes
See the full ranked list of the wealthiest athletes of all time.
Read moreTop 25 Basketball Players
The greatest basketball players of all time, ranked.
Read moreBillionaires & Icons
Profiles of the world's most successful investors and builders.
Read moreGreatest Trades Ever
The most legendary investment decisions in financial history.
Read moreTop 25 Value Investors
The greatest value investors of all time, ranked.
Read moreCelebrity Superpowers
Every celebrity has a superpower. We identified all of them.
Read more