Coco Gauff’s incredible summer, capped off by a US Open title, has once again spotlighted the wisdom of one of tennis’ preeminent strategists, former pro and ESPN analyst Brad Gilbert. Prior to joining forces with Gauff, the Gilbert coaching journey included helping two other players win the US Open soon after they commenced work with him—Andy Roddick in 2003, Andre Agassi nine years earlier. Gilbert was also alongside Agassi for five other Slam victories, including his redemptive 1999 run to glory at Roland Garros.

Two words associated with Gilbert have been part of the tennis lexicon for more than 30 years: winning ugly.

What does “winning ugly” mean? “Winning ugly is finding any possible way to win,” says Ann Grossman, a former pro and CEO of the Women’s Tennis Coaching Association. “It doesn’t have to be perfect.”

But might winning ugly be profoundly misunderstood? How did it surface with Gauff? And why do people resist it?

To demystify what winning ugly means in the year 2023, we went to the source. According to Gilbert, “In the most simplistic way, winning ugly is about figuring out how to win. In a lot of tennis lessons, you’re learning how to hit the ball a little better. But that’s not about competing.”

To grasp the origins of Gilbert’s tennis wisdom, it’s essential to know that he grew up in the San Francisco Bay Area during the ‘70s; specifically, in the Oakland area, where over a five-year-period, championships were won by baseball’s Oakland A’s, basketball’s Golden State Warriors, and football’s Oakland Raiders.

“In every sport,” says Gilbert, “I was always thinking about the strategy: How do you do it? How do you get it done? What are your weapons? What are your weaknesses?”

Five percent of the time you can’t miss and can’t lose to anybody,” he says. “Five percent of the time you can’t beat anybody.” It’s the vast majority of matches, those 90 percent, where a player must engage the mind and determine which disparate tools will work best on that particular day versus the specific opponent. Brad Gilbert


As one example Gilbert has cited, his beloved Raiders had a quarterback named Ken Stabler who was incredibly accurate, but not nearly as proficient throwing long. Stabler was also slow, so more likely to take a sack than attempt a treacherous scramble. In 1976, the year Gilbert turned 15, Stabler led the Raiders to their first Super Bowl victory. Thus the mind of a supreme strategist was born, and the battles of Arthur Ashe Stadium won on the playing fields of the Oakland-Alameda County Coliseum.

Once his pro career began in 1982, Gilbert kept a notebook, filled with insights on his opponents. Did Ivan Lendl prefer to hit his backhand passing shot down-the-line or crosscourt? How did Gilbert alter his return position versus lefty John McEnroe’s wicked ad court serve? What shot did Gilbert need to make even better if he was to make rallies uncomfortable for Jimmy Connors? Why was it productive to direct a few balls to Boris Becker’s strong forehand? All of that data fueled Gilbert’s game plans and improvement areas. This is a far cry from these words often uttered by players: I just need to play my game.

Gilbert views the competitive process across a spectrum. “Five percent of the time you can’t miss and can’t lose to anybody,” he says. “Five percent of the time you can’t beat anybody.” It’s the vast majority of matches, those 90 percent, where a player must engage the mind and determine which disparate tools will work best on that particular day versus the specific opponent.”

That’s precisely what Gauff did in New York. In her last three victories, versus Jelena Ostapenko, Karolina Muchova, and Aryna Sabalenka, Gauff relied heavily on her tremendous court coverage skills to extend the rallies and either extract errors or put herself in a position to drive the ball powerfully into a corner.

Gilbert notes that a player needs to be candid about what he or she is truly capable of. “If you’re not as fast as used to be,” he says, “maybe you’ve got to take a bigger cut at that mid-court forehand than when you were younger and could keep the rally going. As you get older, you might not be able to serve-and-volley as often as you did when you were younger and stronger.”


According to Grossman, “You may know your solution in a certain situation is hitting a forehand angle. But you better put time into practicing that shot if you want to hit it under pressure.”

Yet obvious as all this appears, so many players rarely wed tactics and techniques, even as they cite the importance of the mental game. Over the last 50 years, ever since the publication of Tim Gallwey’s groundbreaking book, The Inner Game of Tennis, there has been increasing acceptance of the need to find emotional tranquility when competing. But the cognitive aspect is frequently neglected. “Way too many players spend time thinking about how they’re hitting the ball or how it feels on their racquet,” says Gilbert. “You’ve got to think about the Xs and 0s.”

Hall of Famer Pancho Segura, a great player who also coached Jimmy Connors, had his thoughts on the causes of the resistance to tactical thinking. Segura noted that tournaments are often played at elegant venues. But the actual competitive process is highly interactive, comparable to boxing or wrestling. To stomach that kind of challenge in such a pleasant environment is jarring. So instead, Segura noted, there flourished a constant desire to think a proper tennis player should focus on beauty and technique over effectiveness and tactics.

“I always liked playing someone who people said was ‘a nice player,’’ Segura once told me. “What that really meant was that he hit the ball well but had no idea how to figure out what was going on inside the lines.”

Along with that comes what could be called the self-indulgence of perfectionism. “A lot of players want every point to go a certain way,” says Gilbert, “and so they think they’re playing poorly and find a way to lose.” It’s the opposite of how longstanding coach Craig Kardon views it.

“Winning ugly has to do with getting the job done,” says Kardon. “You’re in the desert and you’ve got to figure out a way to live.”

Most recreational players watch a match like they’re looking at somebody play Nintendo at a video arcade. They just stare. I’d watch a match like I was studying for a history test. Brad Gilbert and Steve Jamison, co-authors of "Winning Ugly"


While so many competitors struggle to find a single solution, let's not forget how, once upon a time, there was a very successful player who seemed to have all—and was therefore able to pose one question after another to his puzzled opponents. This man would often merely block his forehand service return. During rallies, this man frequently carved a short slice backhand that flummoxed his opponents. Later in his career, he began to drive it more, striking it early in a way that jolted his greatest rival. When a short ball came to his forehand, he relished the chance to occasionally feather a drop shot. His serve was well-placed, though not as fast as the deliveries struck by many of his peers. For a while, he experimented with dashing forward when returning serve, a personal twist on the classic chip-and-charge strategy employed relentlessly by one of his coaches.

If you haven’t guessed yet, this pesky fellow’s name was Roger Federer. Fancy that. The player who has generated more swooning than anyone in tennis history was engaged in an active campaign of disruption built upon variations in speed, spin, court positioning, awareness of the score; a veritable Swiss (sic) Army knife array of tactics. Dare we say that Federer won pretty ugly?

Then again, pros, by design, are committed to generating results and earning a living from tennis. Recreational players like to say they play for fun and aren’t that competitive. Then why keep score? Might it instead be far more comforting to close one’s eyes and surrender to innate physicality?

Says Gilbert, “You ask someone what happened and they’ll just say how badly they played, or that the other guy zoned, or something was up in my head. That doesn’t tell you anything about what really happened.”


Maybe, per Segura, players desire this ostrich-like existence, for to say you were simply hit off the court takes personal accountability off the table. But to admit you were out-thought leaves one feeling implicated and potentially even stupid. Who wants that from a form of exercise?

Perhaps most of all, winning ugly defines a clear-eyed attitude towards competition, propelled by the embrace of tactics and the quest to refine one’s skills so that those sequences can be better executed.

“You learn these things about what works well for you and what doesn’t,” says Gilbert, “and then you put time into little areas of improvement.” The areas Gilbert cites are as obvious as getting in more first serves, improving one’s volley and overhead, cutting down on return errors.

“Most recreational players watch a match like they’re looking at somebody play Nintendo at a video arcade,” Gilbert and his co-author Steve Jamison wrote in Gilbert’s iconic book, Winning Ugly. “They just stare. I’d watch a match like I was studying for a history test.”

Raiders owner Al Davis had a trademark saying: “Just win, baby.” Pay close attention to Gilbert and you’ll see that, should you wish to truly be a competitor, terms like ugly and pretty are mere illusions, worthy of evaporation.