Christopher Clarey's Tennis & Beyond

Christopher Clarey's Tennis & Beyond

Closure Issues

How much more pain can Djokovic take?

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Christopher Clarey
Sep 01, 2026
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Novak Djokovic reacts against Mariano Navone during a Men's Singles match on Day One of the 2026 US Open at USTA Billie Jean King National Tennis...
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“It doesn’t end the way you want it,” said ESPN’s John McEnroe as he watched 39-year-old Novak Djokovic lose in five routinely excruciating sets on opening night at the US Open to a player he once would have used for batting practice.

McEnroe, now 67, says a great many things, too often in the midst of a rally, but he knows all about downbeat career endings. He won the last of his seven singles majors at the US Open in 1984 at age 25 and then played on for more than a decade. His final singles match was a first-round loss to Magnus Gustafsson at the Rotterdam Open in 1996.

There have been exceptions for a select few tennis superstars. Chris Evert, in her farewell, led the US team to victory at the 1989 Fed Cup final, concluding with a victory over Conchita Martinez. Australian Ash Barty retired on her own terms, though much too soon for the rest of us, after winning the 2022 Australian Open at age 25 and has shown no sign of making a comeback. Pete Sampras also won his last tournament – the 2002 US Open, beating archrival Andre Agassi in the final – though it took Sampras nearly another year to make his retirement official.

If we go way back, the poker-faced American Helen Wills walked off in 1938 after winning Wimbledon for the eighth time, never playing singles again.

But much (much) more often, it ends with something closer to a whimper than a roar. See Djokovic’s measuring sticks Rafa Nadal and Roger Federer for confirmation, and I’m referencing Federer’s last singles match, not his ceremonial and deeply moving Laver Cup adieu.

What makes a player great -- self-belief, tenacity, pure talent and innate drive -- can also greatly contribute to them pushing it to a point where it gets hard for the rest of us to watch.

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