Winning Ugly
Brad Gilbert was never the most talented player on tour. He reached world #4 in 1990 and later coached Andre Agassi to multiple Grand Slam titles. His book Winning Ugly (1993) codified his approach: you don’t need the best shots to win matches.
His central claim: “5% of the time you can’t miss, 5% of the time you can’t beat anybody. It’s the 90% where the mind matters.”
In that 90%, Gilbert didn’t try to play perfectly. He played at 65% — consistent, controlled, exploiting opponent weaknesses. He prepared for each match by identifying what his opponent hated and making them play that style.
The philosophy inverts typical tennis instruction. Most coaches emphasize improving your game. Gilbert emphasized degrading your opponent’s. If they have a weak backhand, hit everything there. If they struggle moving forward, drop shot and lob. Make the match about their problems, not your brilliance.
The 65% principle sounds like playing scared. Gilbert argued it’s playing smart. Going for winners increases errors. Errors give opponents free points and confidence. Playing within yourself keeps the ball in play and pressure on the other side.
He claimed strategic thinking alone improved his match win rate by 20%. The number is unprovable, but the logic holds: an inferior player who fights the right fight can beat a superior player fighting the wrong one.
This extends beyond tennis. Competition rarely rewards playing your best game — it rewards playing the game that exploits asymmetries. Don’t compete head-on where opponents are strong. Find the angle they haven’t prepared for.
The concept connects to business strategy (blue ocean, competitive positioning), relationships (meeting people where they are), and creativity (constraints over ambition). Success often comes from constraint rather than showcase.
Related: [[chain-wrestling]], [[first-four-shots]]