for the most career Grand Slam wins with 20—a tie he plans to break by completing a calendar-year Grand Slam at the U.S. Open in September. Tennis’ career prize money leader took home $2.4 million in prize money from his Wimbledon win to add to an already-impressive earnings total. The 34-year-old Serbian star made $30 million of his earnings total off the court, with endorsement deals with companies like Lacoste, Peugeot, NetJets and Austrian tennis equipment maker Head.
Rory McIlroy, regarded as one of golf’s biggest names alongside Tiger Woods and Phil Mickelson, has become one of the sport’s most marketable players as well. The 32-year-old collected $29 million off the course over 12 months, partnering with brands such as Nike, Omega and UnitedHealth Group. McIlroy’s largest on-the-course payday to date was his $15 million prize for winning the 2019 FedEx Cup.
Budding NBA superstar Devin Booker has taken the basketball world by storm, catapulting the Phoenix Suns to the league’s top ranks with help from a rejuvenated Chris Paul. However, Booker’s first championship chase could dash his Olympics dreams: If the NBA finals go to a seventh game on July 22, it would give him a tricky choice between resting up and extending an already-long season.
Like his NBA finals opponent Devin Booker, Milwaukee Bucks swingman Khris Middleton has said he intends to play in the Olympics and is listed on Team USA’s roster. But his status could change if the NBA finals extend to seven games, which would leave the series wrapping up on July 22, just a day before the opening ceremony in Tokyo. Middleton re-signed with the Bucks in 2019 on a five-year, $178 million contract after solidifying his spot as the team’s No. 2 option behind Giannis Antetokounmpo.
A dozen years after his NBA career began, Jrue Holiday is set to represent Team USA for the first time in Tokyo. The only thing standing in his way is the Bucks’ NBA finals battle with the Suns. The 31-year-old guard has a $2 million endorsement portfolio, which includes deals with Nike, Microsoft, ONYX, Momentous, Amp and Panini. He agreed to stay in Milwaukee earlier this year on a four-year contract extension worth at least $134 million.
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