The U.S. Open kicked off in New York City with the sport's biggest names vying for silverware and life-changing prize money. Among them was Novak Djokovic, a 24-time Grand Slam champion who entered the tournament as a perennial favorite. But on Sunday night, the Serbian icon fell in a shocking upset to Mariano Navone, a 25-year-old unseeded Argentine, after a marathon match that stretched nearly five hours and ended just before midnight.

Djokovic, who at 39 is older than most tennis stars when they retire, struggled physically throughout the contest. He was seen limping, cramping, and vomiting on court as his body began to break down. After the match, he described how his back and shoulder gave out, causing his body to "collapse" under the weight of ongoing health issues. The loss marked the first time in two decades that Djokovic failed to advance past the first round of a Grand Slam—his last such defeat came at the 2006 Australian Open. His remarkable streak of 78 first-round wins at majors came to an abrupt end.

Navone, an underdog with much to prove, outlasted the legend in five grueling sets. The victory was a career highlight for the young Argentine, who clinched the win against one of the most decorated players in tennis history. For Djokovic, the defeat was a bitter pill, but financially, the sting is softened by the U.S. Open's generous pay structure.

Every player who reaches the main draw of the singles tournament is guaranteed at least $140,000, win or lose. That means Djokovic will walk away with a six-figure check despite his early exit. And that is just a fraction of his overall earnings. According to Forbes, Djokovic earned $5.2 million on-court last year, but a staggering $25 million off the court through endorsements and business ventures. His sponsor portfolio includes Lacoste, Qatar Airways, Hublot, and General Atlantic, making him the sixth highest-paid player in tennis.

The U.S. Open is not just about glory; it is a financial powerhouse. The tournament has boosted total player compensation to a record $108 million this year, a 20% increase from $90 million in 2025. The majority of that goes to singles players, with $37.84 million allocated for singles rounds and $13 million for doubles. The top prize for the men's and women's singles champions is $5.5 million, with the runner-up taking home $2.8 million. Semifinalists earn $1.45 million, quarterfinalists $780,000, and players eliminated in the round of 16 receive $480,000. Even those falling in the first round of qualifying can earn between $32,000 and $66,000.

Other top players are also in the hunt for the massive payday. Carlos Alcaraz, the 2025 U.S. Open men's singles champion, commands $53.7 million annually, with $38 million from off-court deals. Coco Gauff and Aryna Sabalenka are among the women's stars competing for the $5.5 million winner's check. Italian Jannik Sinner, currently the highest-paid tennis player according to Forbes, earns about $58 million per year, with $35 million coming from partnerships with Allianz, Gucci, and Lavazza. Serena Williams, though retired, still makes $40 million annually through investments and brand partnerships.

For Djokovic, the $140,000 first-round prize is a drop in the ocean compared to his off-court empire. But the loss serves as a reminder that even the greatest champions are not immune to the passage of time. As the U.S. Open continues, the spotlight shifts to the next generation of stars who are chasing both the trophy and the millions that come with it.