Richard Pagliaro | Thursday, August 20, 2026
Photo credit: Prime Video
The summer of the Winter Wolf starts today.
Prime Video’s feature-length documentary exploring the extraordinary journey of Grand Slam king Novak Djokovic premieres today.
The 39-year-old Djokovic has rewritten tennis history more than virtually any champion.
Delivering immortal achievement has felt like both a blessing and a burden, Grand Slam king Djokovic confesses in a new documentary out today.
The highly anticipated feature-length documentary Novak Djokovic: The Wolf in Winter, from director Jason Hehir (The Last Dance), debuts today, exclusively on Prime Video. To celebrate, Prime Video posted this clip of Djokovic reflecting on the mixed emotions winning 101 career championships and spending a record 428 weeks as world No. 1.
Despite all of his success, the 24-time Grand Slam champion said he’s still fueled by inner inadequacy.
“The curse of achieving every possible achievement that you could in our sport is that anything less than that is not good enough,” Djokovic said.
“The feeling of not good enough has been with me for a very long time. It’s still with me.”
Any other player would be lauded for knocking out world No. Jannik Sinner in a five-set thriller to reach the Australian Open final in January and push Carlos Alcaraz to four tough sets as Djokovic did earlier this season at age 38.
The predicament for Djokovic is he’s set such a lofty GOAT standard, anything less than winning can seem substandard.
“Others might try to fool me by saying: Hey, you had a great Australian Open,” Djokovic said, referencing his 2025 AO win over Alcaraz. “You played semis. You beat Alcaraz, one of the best players in the world. You played great, amazing…
“Yeah, yeah, but not good enough.”
Hall of Famer Andre Agassi, who formerly coached Djokovic, said there are powerful, primal and sometimes contradictory emotions that drive the Serbian superstar.
“When I coached him, I really lifted up the hood of what makes him tick,” Agassi said. “He wants to be kind. He wants to care. He wants to be open. He wants to receive.
“But he can’t win when he allows his heart to go there. I was surprised how dark he needed to feel to get the most out of himself.”
Former No. 1 and Tennis Channel analyst Jim Courier said Djokovic is the rare champion who can fight battles on multiple fronts—against his opponent, an unruly fan, his own frustration pursuing perfection, the aging process—and emerge strengthened by those struggles.
“Novak plays best in a slight stage of agitation,” Courier said. “So, there might be one fan who says something that he doesn’t like. And he will make a point to win the match and instead of turning to his team and celebrating, turn and point at the agitators in the stands.”
Though Olympic gold-medal champion Djokovic told the media in Indian Wells in March he aims to play the Los Angeles Olympic Games and defend his gold, Agassi suggests the end of the Serbian’s storied career “when it does come, always comes fast.”
“I don’t know when the end will come for Novak, but the one thing that I can say is that the end, when it does come, always comes fast,” Agassi said. “I would hope for him that he doesn’t wait too long. Not because he can’t win anymore but because tennis takes your childhood.
“But then it gives you the chance to be done with your success so that you raise your children without the preoccupations.”
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