He has had 20 career titles and is an American tennis coach, a television tennis commentator, an author and former professional tennis player. He was born in Oakland, California and graduated from Piedmont High School (California). Gilbert’s career-high singles ranking was world no. 4, which he reached in January 1990. Since retiring from the tour, he has coached several top players, including Andre Agassi, Andy Roddick, Andy Murray, and Kei Nishikori.