Brad Gilbert is a former professional tennis player and tennis coach and podcaster (Winning Uglier). Throughout 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.Since retiring from the tour, he has coached several top players, most notably Andre Agassi who won six of his eight Grand Slam titles under Gilbert's tutelage.