SAN DIEGO—For all Landon Donovan accomplished on the soccer field, there’s one side of him that wonders what life would look like if a point in time was replayed.

As a child, Donovan and his brother split their time participating in soccer and tennis. The Ontario-born, California-raised kid was inspired to pick up a racquet by American standouts Andre Agassi, Michael Chang, Jim Courier, Lindsay Davenport and Monica Seles, and though engrossed by the sport, Donovan opted to pursue the pitch over a court due to greater playing opportunities. From becoming the first U.S. man to notch 50 goals and 50 assists on the international stage and starring on three World Cup squads to winning six MLS Cup titles, that decision paid off in the most remarkable of ways. Yet, the competitor inside Donovan burns with curiosity about the fork in the road he left behind.

“I really wish sometimes that I could have started over and seen how far I could go in tennis because I love how much you have to do it yourself,” Donovan shared with me earlier this week at the San Diego Open. “It's the ultimate challenge being out there on a court against one other person and trying to beat them. I find that really motivating and fascinating. So maybe in another life I get to try tennis.”

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“I usually read the ball pretty well off of another amateur's racquet,” states Donovan.

“I usually read the ball pretty well off of another amateur's racquet,” states Donovan.

After putting away his cleats in 2014, Donovan stayed active by rekindling his tennis roots. For five years, he hit three or four times a week. By getting out on the baseline regularly, Donovan learned new qualities about himself while enjoying the labor required to polish his game. Through that process, Donovan developed a deeper appreciation for the playing environment that had been the center of his life for so long.

“in soccer, if you're having a bad day, you can hide, you can help your teammates play better. You can do other small things to help your team. If you're having a bad day on the tennis court, it's just you,” he says. “And at our level, we don't have coaches or trainers or people helping us through it. You're just out there by yourself dealing with it.

“Having played a sport for a long time, I really value how difficult it is to maintain a level of excellence for so long. So the usual suspects like Fed and Nadal are to me, very special because of what they've done. Serena on the women's side, because she's done it for so long.”

Married and the father of two young boys, the Donovan family relocated to America's Finest City six years ago. In 2019, he co-founded the San Diego Loyal, a USL Championship franchise that debuted in 2020 with Donovan at the helm.

On Tuesday, he was at the Barnes Tennis Center to take in San Diego’s first ATP tournament. Sitting in the bleachers on an outside court, Donovan watched Dan Evans and Fabio Fognini lose an entertaining match tiebreaker to Austin Krajicek and Andreas Mies prior to warming up for a celebrity match that also featured two-time NBA MVP Steve Nash. The two helped raise awareness for the Rady Children’s Hospital during a five-game exhibition that saw Donovan and James Blake top Nash and tournament director Ryan Redondo.

“I grew up relatively American poor, the way I phrase it. We've been handed an incredible life and Steve and I are both aware of that,” says Donovan. “When you have the opportunity to help other people, you should probably do it. My life could have ended up a lot of different ways. This was probably the least likely of all of them. So I feel very grateful for that.”

“Steve would probably beat me in a singles match,” Donovan admits about his head-to-head chances against Nash.

“Steve would probably beat me in a singles match,” Donovan admits about his head-to-head chances against Nash.

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Afterwards, Andy Murray won his opener against lucky loser Denis Kudla in straight sets. Seeing Murray make the trip from France to play in the inaugural 250-level event spoke volumes to Donovan about the former world No. 1’s dedication to his craft.

“I'm just impressed with—based on his story and what he's been through—that Andy Murray is still coming to a place like this in a ‘lower-level tournament’ and wanting to play,” he explains. “I think that tells you everything you need to know about him and how much he loves the game. So people like that that have been endured for so long, I have the most respect for.”

Like Murray, Donovan has world-class instincts, and it’s why he possesses a natural comfort at the net. While playing can bring out moments of aggravation, the pleasurable aspect of trading groundstrokes and volleys wins Donovan's heart every time. For the kid who idolized the likes of Courier and Seles, the now 39-year-old doesn't envision himself in a world without a racquet readily available.

“It's been a challenge since I stopped playing soccer to try to get as good as possible. But it's a sport I'll play for the rest of my life.”