13. Greg Norman
Career earnings: $705 million
Like Shaquille O’Neal and Muhammad Ali before him, Norman sold his future licensing rights to Authentic Brands Group in March. Norman’s company retains control of his real estate, investments and course design operations, but ABG will work on his other business interests in apparel, accessories, steak and wine.
14. Mike Tyson
Career earnings: $700 million
The youngest heavyweight champion in the history of boxing squandered $400 million in earnings (not adjusted for inflation) before filing for bankruptcy in 2003. Tyson has reinvented himself at 51 as an actor and with business partnerships around gaming, motorcycles and fitness centers.
15. Roger Federer
Career earnings: $675 million
Federer recently re-took the crown for highest career prize money on the ATP Tour with his resurgent year on the court in 2017. His $111.9 million tally surpasses the total of Novak Djokovic ($109.8 million), as well as that of Tiger Woods, who sits at $110 million in prize money on the PGA Tour.
16. Lionel Messi
Career earnings: $600 million
Messi has been at Barcelona since age 13, and his contract extension last month will keep him at Camp Nou through the 2020-21 season. The buyout clause for Barcelona’s all-time leading scorer doubled under the new deal to $835 million.
17. Alex Rodriguez
Career earnings: $575 million
A-Rod signed two of the three biggest contracts in the history of baseball during his 22-year career and was paid $20 million by the Yankees in 2017 despite retiring last year. He has been busy in retirement as a Fox Sports analyst and a host for an upcoming CNBC reality show, in addition to his high-profile relationship with Jennifer Lopez.
18. Jeff Gordon
Career earnings: $525 million
Gordon won 93 races during his Nascar career, the modern-day record. He owns a stake in Jimmie Johnson’s No. 48 car and could be in line for a larger ownership role at Hendrick Motorsports.
19. Oscar De La Hoya
Career earnings: $520 million
The Golden Boy’s 2007 fight with Floyd Mayweather was the biggest bout in pay-per-view history, with 2.5 million buys, until Mayweather faced Manny Pacquiao. De La Hoya earned a then-record $52 million because he served as the fight’s promoter through his company Golden Boy Promotions, which he founded in 2002.
20. Manny Pacquiao
Career earnings: $510 million
Pacquiao’s pay-per-view career includes 18.6 million buys and gross revenue of $1.2 billion. The Filipino senator lost to Australian Jeff Horn in his only 2017 bout. Pacquiao’s biggest career payday was his 2015 fight with Mayweather, for which he pocketed roughly $125 million.
21. Derek Jeter
Career earnings: $490 million
Jeter’s tenure as an MLB owner is off to a rocky start in South Florida. The 14-time All-Star put up only $25 million of the $1.2 billion price for the Miami Marlins, but Jeter is calling the shots as CEO of the team.
22. (tie) Peyton Manning
Career earnings: $480 million
The five-time MVP retired as the NFL’s all-time leader in passing yards (71,490) and touchdowns (539) and was the NFL record-holder for earnings on and off the field. Manning remains a popular pitchman in retirement, shilling for Nationwide, DirecTV, Gatorade, Papa John’s and Otterbox. He also hosted the 2017 ESPYs.
22. (tie) Kevin Garnett
Career earnings: $480 million
Garnett earned an NBA-record $334 million in playing salary during his 22-year playing career with the Timberwolves, the Celtics and the Nets. His blockbuster six-year, $126 million contract as a 21-year-old in 1997 helped push NBA owners to lock out the players ahead of the 1998-99 season.
24. Evander Holyfield
Career earnings: $475 million
Holyfield’s career-high payday was $34 million, for his second fight versus Mike Tyson, which ended abruptly when Tyson was disqualified for biting off a chunk of Holyfield’s ear. Despite a quarter-century of boxing purses, Holyfield faced major financial issues with a foreclosure of his $10 million, 109-room Atlanta estate and lawsuits for unpaid child support.
25. Andre Agassi
Career earnings: $470 million
Agassi’s massive Nike endorsement deal earned him $140 million over 10 years, including the appreciation of the company stock he received in the pact.
