Novak Djokovic’s shocking US Open loss looked like the inevitable beginning of the end

NEW YORK NEW YORK - AUGUST 30: Novak Djokovic of Serbia reacts during a changeover against Mariano Navone of Argentina during their Men's Singles First Round match on Day One of the 2026 US Open at USTA Billie Jean King National Tennis Center on August 30, 2026 in the Flushing neighborhood of the Queens borough of New York City. | Getty Images The first day of this year’s US Open saw the tournament’s first major upset. Novak Djokovic, a four-time champion in New York, came into Sunday night’s session as the all-time leader in men’s US Open victories. And, even at his advanced pro tennis age of 39, he’s remained a contender this year, making it to the Australian Open final and the semifinals at Wimbledon. On this night, though, he looked like a player deep into his decline: after 4.5 grueling hours, Djokovic’s 2026 Queens campaign ended before it really began, 7-6 (5), 5-7, 4-6, 6-2, 6-1. His loss came at the hands of Mariano Navone, a relatively unknown 25-year-old Argentinian, ranked 49th in the world. He became the first opponent to defeat Djokovic in the first round of a major tourney since 2006. Djokovic, back then, had a reputation as a talented young player, but one who was too rude and unresilient for his own good. While that first negative quality has not changed in the minds of many—even in his later years, he’s added new kinds of sassy flair, like his racquet-as-violin celebration—the idea of Djokovic as unsturdy has long since reversed. For the past decade and a half, he’s been the spitting image of unbreakable stamina, outlasting both of his rival-peers, Rafael Nadal and Roger Federer, and collecting a 42-12 record in five-setters. There’s a thing they say about human lives, though, and it seems to be true about certain great sporting careers too: you go out the way you came in, helpless as a child; wilting as a rookie would. While Djokovic has done everything an athlete possibly can to maximize his biology, it would seem that nature has caught up to him, at least for now, and given us a sharply visible preview of the end, if nothing else. Can he squeeze a little more out of the rind of himself, and make it a little closer to his stated goal of playing in the 2028 Los Angeles Olympics? Possibly. Over the course of his career, he’s been especially good at off-season optimization, pouncing on less maniacally dedicated players when the season begins in Sydney every January; don’t be surprised if he makes it deep there, once again, just a four months from now. But the man who was puking in front of cameras on the Flushing Meadows court, Sunday night, then crying mid-set as he realized he had no fight left in the fifth, is a man we will be seeing more and more often—unless, of course, he calls it quits. That such a withering soul is also the greatest tennis player of all time will be an increasing source of cognitive dissonance. It was this inevitable, tragic mortality that so fixated the makers of “Rafa,” the docu-series recently released by Nadal on Netflix. Djokovic’s own docu-content, “The Wolf in Winter,” just came out on Amazon Prime, fleshing out the complex inner contours of a superstar who has achieved a rare balance of greatness and villainy. The documentary shows something of the sacrifice that goes into Djokovic’s greatness, including a self-manipulation that brings him into a state of darkness that’s necessary for his on-court conquests (on this, his one-time coach Andre Agassi is especially eloquent). As the ESPN cameras cut to Djokovic’s progressively glum family sitting in his box, and as a smile came across his face for the first time, all night, only when it was over, it was fair to wonder how much fang is still in that wolf. Afterwards, in his press conference, he said he “just struggled all the way since the fourth game of the match. When it comes to match itself and overall feeling of how I felt with body and playing, it was really not enjoyable. I pretty much despised every moment that I spent on the court for that.” These are not the words of the unquitting warrior that tennis fans have become so used to. But, after watching him grimace with agony all evening, how could we expect him to say anything else?

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