

A cerebral tennis maverick who used strategic guile to outthink more powerful opponents, then masterminded the careers of champions as a coach.
Brad Gilbert's tennis story is one of intellect over instinct. In an era of booming serves and flashy winners, the Californian carved out a top-five ranking with a game he famously described as 'winning ugly.' He was a master tactician, dissecting opponents' weaknesses with relentless consistency, clever spins, and a frustratingly effective two-handed backhand. His professional career yielded 20 singles titles, an Olympic bronze in 1988, and victories over every major star of his day. But his true legacy was forged after he retired. As a coach, he became the sport's premier 'tennis brain,' transforming raw talent into Grand Slam champions. His most famous partnership was with Andre Agassi, whom he guided from a ranking outside the top 30 to world number one and six major titles. Gilbert later authored the bestselling instructional book 'Winning Ugly,' distilling his philosophy for a generation of players and fans who appreciated the mental chess match behind the physical spectacle.
1946–1964
The largest generation in history at the time. Shaped by postwar prosperity, the Vietnam War, the sexual revolution, and Watergate. They questioned every institution their parents built — then ran them.
Brad was born in 1961, placing them squarely in the Baby Boomers. The events that shaped this generation — postwar prosperity, civil rights, Vietnam, and the counterculture — shaped the world they entered and the choices available to them.
The biggest hits of 1961
#1 Movie
101 Dalmatians
Best Picture
West Side Story
#1 TV Show
Wagon Train
The world at every milestone
Yuri Gagarin becomes the first human in space
Star Trek premieres on television
Nixon resigns the presidency
Star Wars premieres; Elvis dies
Iran hostage crisis begins; Three Mile Island accident
Michael Jackson releases Thriller
Soviet Union dissolves; World Wide Web goes public
September 11 attacks transform the world
Osama bin Laden killed; Arab Spring sweeps the Middle East
January 6 Capitol breach; COVID vaccines roll out globally
He is known for creating colorful nicknames for players, famously dubbing Roger Federer 'Fed Express' and Pete Sampras 'Pistol Pete.'
He won the 1981 Maccabiah Games gold medal in singles and a silver in doubles.
He has served as a television commentator and analyst for ESPN for many years.
As a junior, he was ranked number one in the United States in the 18-and-under division.
“I made a nice living out of beating guys who were better than me.”