The Captain and The Maestro

When to walk away: It’s the most difficult decision a great athlete will face, and it’s often one of the few that they get wrong. Muhammad Ali hung on too long in the ring and was pummeled for it. Pete Sampras, after taking months to make up his mind, admitted later that he may have left too soon. Michael Jordan had to retire three times before he finally stopped playing basketball. Martina Navratilova was still playing at age 50.

As another ageless wonder, Jimmy Connors, once said, it’s hard to live without the applause.

For most of 2014, it seemed that New York Yankees shortstop Derek Jeter had managed his disappearing act flawlessly. After hobbling through a series of injuries and playing just 17 games in 2013, the 40-year-old future Hall of Famer had announced that this, his 20th season, would be his last. He said he knew what he wasn’t capable of anymore, and he didn’t want to embarrass himself by hanging on too long. Jeter was right; he had his worst full season since his rookie year in 1995.

At first, everybody seemed to understand. Fans came out in droves to say goodbye to The Captain on his farewell tour. Rival teams honored him as if he were one of their own, and showered him with increasingly over-the-top parting gifts. Whether you loved or loathed the Yankees, you couldn’t deny that Jeter, who was both a charismatic star and an all-business professional, had “done things the right way.”

But as I said at the top, exits aren’t easy, and somewhere along the line Jeter’s began to rub some people the wrong way. His retirement tour was "too much" and a distraction to this team, they said, and his manager Joe Girardi should have benched him. Others began to whisper that Jeter wasn’t all that great in the first place; he has never fared well when measured by baseball’s newfangled Sabermetric stats. That whisper turned to a scream—or at least a very loud whine for attention—when ESPN’s Keith Olbermann launched an all-out, and nonsensically one-sided, attack on Jeter as he was preparing for his final send-off.

In the end, of course, Jeter made Olbermann and his fellow naysayers look like hopeless killjoys. In his last game at Yankee Stadium, Mr. November won it with a walk-off hit in his final at bat. But the ups and downs of his long goodbye made me wonder if there was anything that tennis’ version of Derek Jeter, Roger Federer, could learn from the experience when he finally decides to hang up his own set of sticks.

The first question that tennis fans might ask is: Do we want to see Federer, like Jeter and Andre Agassi in 2006, take an extended victory lap? Not all tennis players go out that way. Steffi Graf lost the Wimbledon final in 1999 and essentially vanished. Andy Roddick called the press together at the 2012 U.S. Open and said that tournament would be his last. Obviously, Federer can stop playing whenever and however he wants, and after his resurgent 2014, it’s not anything he needs to think about right now. Letting the mic drop with the Davis Cup in his hand at the end of this season would also have a poetic ring to it.

But to me, a last go-round at each of the majors would be fitting. Few athletes in any sport have enjoyed the global support that Federer has, and it has helped sustain him into his 30s. These days, some fans seem distinctly disappointed when they come to a tournament and don't catch a glimpse of Federer. From now until the day he quits, there will be The Maestro, and there will be everyone else.

If Federer goes the farewell-tour route, will he start to face the same whispers that Jeter did, that he’s a distraction, that he hung on too long, that he really wasn’t the greatest player ever to pick up a racquet? If there’s one warning that Jeter offered, it’s that a great athlete needs to know when he’s not so great anymore. At the start of 2014, I thought Jeter might be leaving too early; by the end, I knew I was wrong and he was right. Physical decline can happen quickly, and I don’t think anyone wants to see Federer limp to the finish line.

But I highly doubt he’ll suffer a Jeter-esque backlash. For one thing, it’s much more difficult to make the case that Federer was overrated. Sabermetric stats are valuable in team sports, where an individual’s contribution can be hard to quantify. But in tennis, you’re pretty much as good as your ranking and your record say you are, and Federer’s record remains second to none. There are some who now claim that he benefited from a “weak era” of competition, but that’s a hard case to make considering that Rafael Nadal has been part of his era since 2005, and in that time Federer has won 13 majors and finished No. 1 four times.

In the end, it won’t be the haters or the historians who define how Jeter and Federer go out. It will be the fans. Each man has spent the last 15-20 years earning their respect. Each has played with a free-flowing flair that masked the hard work which made it possible. Each is a link to the past—Jeter is the Last Great Yankee; Federer is the final, fraying thread that connects today’s men's game to the way it was played in the 20th century. Each struggled at first with sky-high expectations as teenagers, before eventually exceeding them. As players, each was known, first and foremost, for consistency, for winning, for clocking in every day.

That’s why fans came out in ballparks around the country this year to see Jeter one last time, and why they paid $900 a pop to be present for his final game at Yankee Stadium. On those days and nights, no one cared what his Saber stats were, or whether his defensive range wasn’t what it had been cracked up to be. They knew what a star, and a winner, and a guy who never disgraced the game looked like, and they wished he had spent the last 20 years helping their team win.

The same will be true for Federer, and the cheers will echo all over the world. Having sat in stadiums to watch him in Melbourne, Indian Wells, Paris, Wimbledon, and New York the last few years, I would say from the reactions of fans that his long farewell tour has already begun. At this year's Wimbledon final, I thought I had never heard a crowd cheer as loudly for him. Then I heard the crowd in Arthur Ashe Stadium the night he came back to beat Gael Monfils. We’ve already imagined tennis without Federer, and decided that we want to see as much of it with him as we can. Federer described his welcome on an exhibition tour of South America two years ago as an overwhelming experience; it will be the same, and maybe even then some, when he plays in India in December.

The Captain and The Maestro—their nicknames sound different but are ultimately synonymous. Each deserves to go out on his own terms, commanding and conducting the stage as only they have, to the biggest audiences possible, in as many places as possible. Jeter never humiliated himself in his final season, and he finished with a flourish. Federer, who is back in the Top 3 and could win his first Davis Cup in 2014, is poised to do the same. It’s not often we get to see a star and a winner walk away with something close to his best. It’s not often we get a chance to come together and agree on someone. If it ends up being "too much" for some, or going on for too long, well, we only get a chance to say goodbye once.