Our collective attention has turned, appropriately so, to baseball playoffs and football. But if you’ll allow me to interject with my first post here, a story that has not yet received its due attention on this space is the retirement of Andy Roddick. (Confession: it has not received its attention because I happily agreed with a suggestion from Bry that I write about it, so he has held off, and it’s taken me this long to write it. Look, it’s been a busy month, and as you’ll no doubt come to agree, I’m not the best writer. So it took a little while. If the content below or the fact that it comes so late irritates you, feel free to ask the powers that be to revoke my posting privileges. Or better yet, say so in the comments. I can take the heat.)
When he won the 2003 U.S. Open at age 21 and finished the year as the world’s number 1 player, it seemed clear that Andy Roddick was on his way to multiple major titles and accordingly as the successor to Sampras and Agassi as the Next Great American Tennis Player. What wasn’t clear, though, was that Roddick’s run that year at Wimbledon would be far more telling. He had a fine tournament, but lost in the semifinals to another promising young player looking for his first major championship, Roger Federer. The rest, as they say, is history.
Some will remember Roddick for what he had, a powerful forehand to complement one of the most devastating serves ever unleashed, and for what he didn’t have, multiple major championships. Of course, Federer had a lot to do with that. Four times they met in a major final, and four times Roddick had to watch Federer hoist the championship trophy. It is fair to say that Roddick essentially spent a the better part of a decade looking up at, chasing, and failing to reach, Federer. His career record against Federer was 3-21, which gives Roddick the distinction of being the man who has lost to Federer the most.
Roddick’s failure to best Federer is most typified by his 5th set, 16-14 loss in the Wimbledon final in 2009. I suppose Roddick will be long remembered for that match. But I hasten to say that it will likely be for the wrong reasons. To most, it represents him failing to overcome Federer. And there is no question that it embodies that notion quite succinctly and efficiently. But to me, it represents quite a different story.
To tell this tale, we must look back over the arc of events since Roddick’s victory at the U.S. Open in 2003. A few months later Federer began to assert a dominance unlike any other in modern men’s tennis. In three of the next four years he won three majors and in the other year he won two majors. For four years, the only times Federer lost in a major were as follows: a 5th set (9-7) loss in the semifinals of the 2005 Australian Open to eventual champion Marat Safin (himself a 2-time major champion and former world number 1), and at the French Open in 2004 to a 3-time French Open champion (Gustavo Keurten, a former world number 1), and at the French in 2005-2007 to the greatest clay court player of all time (Nadal, whose resume needs no stating).
2003 came to a close with Roddick as the number 1 player and Federer a close 2nd. What had looked like a close race at that point wasn’t anything of the sort. Federer was the roadrunner. Roddick became the coyote, never catching his prize despite his constant pursuit and trying everything he and his coaches could think of. To keep up with the increased power of the game he gained weight and tried outslug opponents from the baseline. Over time injuries took its toll, and his forehand became less of a weapon and more of a looping, keep-the-point-going shot. He dropped weight to become more mobile. He improved his backhand, his volleying, and attacked the net more. He improved his return game. By his late 20s, when most men are retiring from tennis, he had reinvented himself as more of all-court player, albeit one who never seemed totally at ease with that style of play.
And it all culminated at Wimbledon in 2009. In the semifinals, Roddick faced Andy Murray—the hope of Great Britain, the man most likely to break the death grip held by tennis’s Big 3. Murray was a natural all-court player, complete with crafty drop shots and the brilliant return game. Murray was supposed to break through and play the all-court style that could take down the likes of Federer. In the semifinal, with the crowd firmly pulling for Britain’s hope for a men’s major champion at home, Roddick not only won, he did so by out-Murraying Murray. And then, of course, there was the final. And while some look at that match as “Roddick lost again to Federer, failing again to win a second major title while Roger won his record-breaking 15th” I look it at as “Roddick—after retooling so much of his game, and after all the previous defeats—took Federer, the greatest player in the history of tennis, to 16-14 in the 5th set.”
There is no question that, as a player, Roddick was not in the class of Federer. But in his decade of trying to reach Federer—through all the serves, through all those times he bounced out of his chair while his opponent waited out the change-over, through all the sweat-soaked hats, through the reinvention of his game, through that brilliant semifinal win and even more brilliant final loss at Wimbledon in 2009—something totally unexpected and all the more remarkable happened: Roddick became nothing short of a modern day Sisyphus, consigned to a fate of perpetual striving but never attaining his elusive goal. Through it, Roddick demonstrated a quality of character he could not have otherwise shown. The kind of character that keeps a competitor pushing in face of the obstacle he could not overcome, the kind of character that has him face up to the questions after all the defeats as Roddick always did, the kind of character that recognizes that in spite of all of the effort there are some things more important than the next title, as Roddick did when, rather than defend his title at a tournament in Dubai in 2009, he pulled out over their refusal to grant a visa to Shahar Peer at the women’s event.
At the age of 21, Roddick was seemingly on his way to winning multiple major titles and becoming the Next Great American Tennis Player. Through his failure at achieving the former, and in ways no one could have anticipated, he indeed accomplished the latter.

