Brad Gilbert, author portrait
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Brad Gilbert

American
Born 1961
Brad Gilbert is an American former professional tennis player, tennis coach, and tennis commentator and analyst for ESPN. During his career, he won 20 singles titles and achieved a career-high singles ranking of world No. 4 in 1990, and a career-high doubles ranking of world No. 18 four years prior. He won a bronze medal at the 1988 Olympics, and both a gold medal and a silver medal at the 1981 Maccabiah Games.
On LuvemBooks, we've reviewed Winning Ugly.
1
Books Reviewed

In Brad Gilbert's own words

Brad Gilbert discusses the mindset, tennis strategy, and coaching experiences behind 'Winning Ugly' during an Authors at Google interview with co-author Steve Jamison.

Uploaded by Talks at Google, 2015 · Watch on YouTube

Also in conversation

Pursuing perfection versus being good enough

Gilbert explains that while coaching Andre Agassi, he stressed that seeking perfection is an impossible trap that causes misery. He taught Agassi to focus on reliable, fundamental tennis that is simply good enough to beat the opponent across the net.

Floyd Mayweather as winning ugly

Gilbert identifies boxer Floyd Mayweather as the ultimate example of winning ugly in modern sports. While critics label his defensive, low-risk style boring, Gilbert views his ability to outpoint opponents without taking damage as pure genius.

Developing American tennis players on clay

Gilbert contends that American men's tennis has lagged behind Europe because young US players grow up primarily on fast hard courts. He insists that developing juniors on clay is vital for teaching tactical discipline, movement, and patient point construction.

Andre Agassi's photographic match memory

Gilbert recalls being stunned during their early coaching sessions by Andre Agassi's extraordinary mental recall. Without needing video footage, Agassi could accurately break down every shot and strategy from long 17-ball rallies point by point.

Ivan Lendl's deathbed locker room remark

Gilbert recounts losing to Ivan Lendl for the 16th consecutive time in 1991 after blowing a 5-1 third-set lead while playing through an ankle fracture. Afterwards in the locker room, Lendl delivered an brutally memorable psychological jab.

Ask LuvemBooks about Brad Gilbert

Brad Gilbert is a former world No. 4 tennis player turned coach and ESPN analyst who brings a strategist's eye to the page. We have reviewed 1 of their books: Winning Ugly: Mental Warfare in Tennis, written with Steve Jamison, which lays out a concrete system for beating opponents through pre-match preparation, pattern recognition, and mental discipline rather than stroke mechanics — and it holds a 4.6/5 reader rating from over 2,100 Amazon ratings.
Where should I start?
Start with Winning Ugly: Mental Warfare in Tennis — it's the one Brad Gilbert book we've reviewed, and it's their defining work. The book lays out Gilbert's system for outthinking and outplaying opponents without overhauling your strokes, and it holds a 4.6/5 reader rating from 2,192 Amazon ratings.
What's their writing style?
Based on Winning Ugly, Brad Gilbert (writing with Steve Jamison) favors a practical, system-driven approach over abstract theory. The book is organized around a usable framework — pre-match preparation, spotting hidden patterns in an opponent's play, and applying ruthless mental discipline — rather than technical stroke instruction. The Simon & Schuster edition describes it as "the bible of tennis instruction," which speaks to its direct, playbook-like character.
Books we've reviewed
We've reviewed 1 Brad Gilbert book. Winning Ugly: Mental Warfare in Tennis (with Steve Jamison) presents Gilbert's system for winning through strategy and mental toughness rather than stroke changes — a Sports genre title with a 4.6/5 reader rating from 2,192 Amazon ratings.
What genre do they write?
Brad Gilbert writes in the Sports genre, specifically tennis instruction. Winning Ugly: Mental Warfare in Tennis focuses on the strategic and psychological side of the game — preparation, pattern recognition, and mental discipline — rather than physical technique.
Why is Winning Ugly so well known?
Winning Ugly has become a landmark tennis instruction book — the Simon & Schuster edition calls it "the bible of tennis instruction." Its appeal lies in Gilbert's counterintuitive premise: you don't need better strokes to win more, you need better preparation, sharper pattern-reading, and stronger mental discipline. Readers clearly agree, giving it a 4.6/5 rating across 2,192 Amazon ratings.
Who is Brad Gilbert?

Who is Brad Gilbert?

Brad Gilbert is an American former professional tennis player, coach, and ESPN commentator and analyst. During their playing career, they won 20 singles titles and reached a career-high singles ranking of world No. 4 in 1990, along with a career-high doubles ranking of world No. 18 four years earlier. They are best known in the book world for Winning Ugly: Mental Warfare in Tennis, co-written with Steve Jamison.

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