Tennis has always had its share of champions who seemed destined for greatness. But it has also produced another, perhaps more fascinating, category: the players who could have achieved so much more.
When we talk about tennis underachievers, however, we need to make an important distinction. There are two fundamentally different kinds.
The first are the players who were, quite literally, their own worst enemies. They had the game, the athleticism and often the natural talent to become champions, but something within them kept getting in the way. Their temperament, inconsistency, lack of discipline, injuries or inability to maintain focus prevented them from turning extraordinary ability into extraordinary results.
Marat Safin is probably the poster child for this category. At his best, Safin looked almost unplayable. He had the size, power and athleticism to overwhelm virtually anyone, and when he was locked in, he could make the greatest players in the world look ordinary. Yet Safin could also lose concentration, become frustrated and simply drift out of matches. He won two Grand Slam titles, which is hardly a disappointing career, but watching him play always left you with the feeling that there should have been more.
Goran Ivanisevic is another obvious case. His serve was one of the great weapons in tennis, and his left-handed game made him a nightmare on grass. He eventually won Wimbledon in 2001, but only after three previous runner-up finishes. His career almost feels like a movie about a brilliant player who spent years trying to overcome himself.
Henri Leconte is an even more extreme example. At his best, Leconte had a magical combination of touch, flair, athleticism and creativity. He could produce shots that seemed almost impossible. But he never possessed the consistency or competitive discipline necessary to turn that brilliance into sustained success. In another life—or perhaps with another temperament—he might have been a Grand Slam champion.
Grigor Dimitrov belongs on this list too. "Baby Federer," as he was once called, carried enormous expectations from the beginning. He had the complete game, beautiful movement and enough shot-making ability to compete with anyone. He eventually won the ATP Finals and reached a Grand Slam semifinal, but for years his career seemed to be a series of tantalizing glimpses of what might have been.
It is still too early to close the book on Nick Kyrgios, but the question is unavoidable. Few players of his generation possessed his combination of serve, touch, improvisation and sheer shot-making ability. His victories over the best players often demonstrated just how extraordinary his ceiling was. The problem was that his ceiling was rarely his everyday level. Kyrgios didn't merely have bad days; at times, he seemed almost uninterested in finding out how good he could actually become.
You could even put Boris Becker and John McEnroe into this category, although doing so requires some qualification. Both had phenomenal careers and are unquestionably among the all-time greats. Yet that is precisely why the argument can be made. When you consider the talent each possessed, there is a legitimate case that they could have won even more. Their temperaments were part of what made them compelling, but they were also occasionally their undoing.
Then we come to the second—and perhaps more tragic—category: players who were simply born at the wrong time.
Andy Roddick is the first name that comes to mind. He won one US Open and reached four other Grand Slam finals. Under ordinary circumstances, that might have been the foundation of a multiple-major career. Instead, he spent the defining years of his career staring across the net at Roger Federer.
Federer wasn't merely another great player. He was an all-time phenomenon. Roddick's misfortune was that even when he was playing brilliantly, there was often someone better. And when Federer wasn't standing in his way, Rafael Nadal and Novak Djokovic were waiting around the corner. Roddick didn't fail to become a great player. He became a great player during perhaps the worst possible era in which to be one.
David Ferrer may have an even stronger claim. He was remarkably consistent, physically relentless and mentally tough. He reached a Grand Slam final, spent years near the very top of the rankings and beat virtually every player outside the Big Three with regularity. But Ferrer's career was defined by the cruel reality that being the fourth-best player in the world is a wonderful achievement—unless the three players above you are Federer, Nadal and Djokovic.
Lleyton Hewitt is an interesting case because he actually managed to break through before the full force of that era arrived. He won two Grand Slam titles and became world No. 1. But his career was subsequently squeezed by the emergence of Federer, Nadal and Djokovic. Hewitt's decline also illustrates how unforgiving tennis can be: a player who had once been the standard suddenly found himself trying to compete with a generation of players who were rewriting the standards altogether.
Which brings up a certain Andy Murray. Calling Murray an "underachiever" may sound absurd. He won three Grand Slam titles, reached eleven major finals, won Olympic gold twice and became world No. 1. Yet even Murray's extraordinary résumé somehow reinforces the argument.
Put Murray in almost any other generation and his trophy cabinet probably looks dramatically different.
Instead, he spent his prime in the Federer-Nadal-Djokovic era. Three of the greatest players in tennis history occupied the same generation, and Murray had the misfortune of being good enough to challenge all three but not quite good enough to consistently surpass them.
That may ultimately be Murray's greatest frustration—and perhaps his greatest achievement. He wasn't merely a very good player trapped behind the Big Three. At times, he was good enough to beat them all.
Kei Nishikori and Dominic Thiem represent the next generation of what-if players. Nishikori reached a Grand Slam final and established himself as one of the most talented players of his generation, but injuries repeatedly interrupted his career. Thiem, meanwhile, actually managed to break through, winning the US Open in 2020 after reaching three other major finals. But his career was squeezed between eras, and injuries ultimately robbed him of the chance to discover just how much more he could have accomplished.
The phenomenon goes back much further. Michael Stich, Richard Krajicek, Pat Rafter, Michael Chang and Mark Philippoussis all had the misfortune of playing during the Sampras-Agassi era. Stich won Wimbledon and Krajicek won the tournament in 1996. Rafter won consecutive US Opens. Chang won the French Open at just 17. Philippoussis reached two Grand Slam finals but how many more majors might they have collected had they not been competing during a period when Pete Sampras and Andre Agassi were taking up so much of the oxygen?
That is the great injustice of tennis: careers are judged by trophies, but trophies are profoundly dependent on timing.
For me the most fascinating case is Vitas Gerulaitis. The Queens native almost belongs in both categories. He had to compete against Connors, Borg and McEnroe—three players who collectively defined an era. That alone makes his career look somewhat unlucky. But Gerulaitis was also capable of inconsistency and self-sabotage. He reached two Grand Slam singles finals and won the Australian Open, yet there was always the sense that his talent could have produced more.
Maybe we need to refrain from using "underachiever" as synonymous with "disappointment."
Safin was an underachiever as he couldn't always control himself. Leconte never reached his true height as brilliance came more naturally to him than discipline. Kyrgios struggles as his motivation has often seemed to be as unpredictable as his shot selection.
Roddick, Ferrer and Murray are different. Their careers weren't failures of character or ability. They were, to a significant degree, victims of history. That may be the cruelest fate of all.
Imagine being good enough to become a multiple Grand Slam champion, only to discover that your career coincided with Federer, Nadal and Djokovic.Sometimes being great isn’t good enough when you play in the era with the apex of the game’s legends,
That is the real tragedy of the tennis underachiever. A player can lose to himself but he a;so may be defeated by history and occasionally, as with Gerulaitis, he loses to both.
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