Brad Gilbert wasn’t supposed to be a top-five player. Honestly, if you looked at his strokes in a vacuum, you’d probably think he was a local club pro with a decent slice. He didn't have the liquid-gold forehand of Pete Sampras or the terrifying serve of Boris Becker. Yet, he beat them. All of them. In 1989, he tore through a draw in Cincinnati that included Sampras, Michael Chang, Becker, and Stefan Edberg. Four future Hall of Famers. Gone.
How? He out-thought them. He got under their skin. He won "ugly."
When Winning Ugly Brad Gilbert first hit the shelves in 1993, it was a bit of a shock to the system. The tennis world was obsessed with technique. Everyone wanted the perfect follow-through. Gilbert basically showed up and told everyone they were "brain-dead" for worrying about their form while losing to players they should be beating.
The "Who's Doing What to Whom?" Philosophy
Most recreational players are in a trance. You've seen it. Maybe you've done it. You go out there, hit some balls, and hope for the best. If you lose, you blame your backhand. If you win, you think you "found your rhythm."
Gilbert says that's nonsense.
The core of the Winning Ugly Brad Gilbert strategy is a single, piercing question: "Who's doing what to whom?" It sounds simple, almost caveman-like, but it’s the most important metric in a match. Are you letting your opponent dictate with their forehand? Is their second serve sitting up like a ripe plum, and you're just dinking it back?
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Winning isn't about hitting the ball harder. It's about making the other guy miserable.
Gilbert famously took a struggling Andre Agassi and turned him into a Grand Slam machine by teaching him this exact lesson. Agassi wanted to hit winners. Gilbert told him to hit "big targets" and let the opponent choke. He shifted Agassi's focus from "how am I hitting it?" to "how can I ruin his day?"
Why You Should Never Serve First
This is one of the most controversial tips in the book. Most people win the toss and immediately choose to serve. They want to set the tone.
Gilbert thinks that's a mistake. He argues that most players are nervous at the start of a match. Their feet are heavy. Their serve isn't dialed in yet. If you receive first, you put the pressure on them to hold while they're still shaking off the cobwebs. If you break them in the very first game, you've gained a massive psychological edge before you've even bounced a ball for your own serve.
It’s about "grabbing the early lead." It’s about being a front-runner.
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The Seven Hidden Ad Points
In Winning Ugly Brad Gilbert also breaks down the "Hidden Ad Points." These aren't just 30-40 or Ad-In. These are the moments that shift momentum.
- The first point of every game: It sets the vibe.
- The 30-30 point: This is the fork in the road.
- The first point after a break: Don't let them back in.
If you play these points with 10% more focus than the others, your win rate skyrockets. You don't need a better serve for that. You just need to be awake.
Most people "zone out" during a match. Their minds wander to what they're having for dinner or that annoying guy on the next court. Gilbert demands total engagement. He used to take notes. He'd watch his opponents like he was studying for a history test. He knew if McEnroe was getting frustrated, he should slow the pace down even more. He knew if Connors was fired up, he shouldn't give him any "fuel" by arguing with the ref.
Equipment as a Weapon
Gilbert devotes an entire chapter to gear. This isn't about the newest $300 racquet. It's about preparation.
Do you have two racquets? What if you break a string at 4-4 in the third? If you only have one frame, you're done. You've lost. He also talks about water. He calls it the best energy drink ever made. People ignore it because it's free, but hydration is a tactical advantage. If you're fresh in the third set and your opponent is cramping, you've "won ugly" without hitting a single winner.
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The Legacy of the "Ugly" Game
People still mock the title. They think it means playing "bad" tennis.
It doesn't.
It means playing smart tennis. Recently, Gilbert returned to the coaching spotlight with Coco Gauff. You could see the "Winning Ugly" DNA in her 2023 US Open run. She wasn't always playing her best. Her forehand was shaky at times. But she stayed in points. She made her opponents hit one more ball. She found a way.
That is the essence of Winning Ugly Brad Gilbert. It’s the realization that 95% of the time, you won't have your "A-game." If you can only win when you're playing perfectly, you're going to lose a lot of matches.
Actionable Next Steps for Your Next Match
If you want to start implementing this, don't try to change your strokes. Change your head.
- The Pre-Match Scout: Don't just hit aimless rallies in the warm-up. Look at your opponent. Can they hit a high backhand? Do they look winded after three sprints? Find the leak in their boat.
- The 0-0 Break: Next time you win the toss, choose to receive. See how it feels to put the pressure on them early.
- Note-Taking: After your match, write down three things that actually happened. Not "I played bad," but "I kept hitting to his forehand even though he was killing me with it."
- Manage the "Set-Up" Games: When it’s 4-4, stop going for lines. Play high-percentage tennis. Let them be the ones to freak out.
Winning isn't a beauty contest. The trophy doesn't care if your backhand looked like Roger Federer's or a wounded duck. It only cares that you got to 6-4, 6-4.
Stop trying to play pretty. Start trying to win.