Novak Djokovic is rarely one to shy away from big conversations, and at Fanatics Fest in New York he tackled perhaps the biggest one of all: when does it end? Speaking candidly about the twilight of his career, the 39-year-old Serbian star referenced a comment made by Andre Agassi that clearly struck a nerve.

Agassi, the eight-time Grand Slam champion who coached Djokovic during 2017 and 2018, appears in Djokovic's upcoming Amazon Prime Video documentary, titled Novak Djokovic: The Wolf in Winter, set to premiere on August 20. In it, Agassi delivers a memorable line about his former charge: that he does not know when the end is coming for Djokovic, but he is certain that when it arrives, it will arrive fast.

Djokovic says he finds that assessment hard to argue with. He acknowledged that hearing how all-time greats approached the process of letting go has been genuinely illuminating, and he admitted openly that retirement thoughts do cross his mind. Still, he was quick to point out that his results remain strong. He reached the Australian Open final and the Wimbledon semifinals this year, and as recently as March he sat at world No. 3 before sliding to seventh in the rankings.

The champion reflected on the different ways careers can end: athletes who leave on top, those whose bodies force the decision, and those who simply find themselves outpaced by younger competition. He suggested his own exit might involve some combination of all three.

For now, Djokovic says he is focused on enjoying competition while it lasts. TennisDraw users will want to keep a close eye on how bracket predictions shift as Djokovic's schedule and form evolve through the rest of 2025.