Since retiring from the professional tour, he has coached several top players, most notably Andre Agassi who won six of his eight Grand Slam titles under Gilbert's tutelage.

[1] Brad began playing tennis at age 4 after his father, Barry Gilbert (a history teacher and owner of a real estate firm), took up the sport.

He competed for the US in the 1981 Maccabiah Games in Israel, losing in the men's singles finals to Israeli Shlomo Glickstein, but winning a gold medal in doubles with Jon Levine over fellow Americans Rick Meyer and Paul Bernstein.

He became an All-American and reached the finals of the 1982 NCAA Championship, losing to Mike Leach of Michigan 7–5, 6–3.

[5] Gilbert joined the professional tour in 1982 and won his first top-level singles title later that year in Taipei.

His first doubles title came at the 1985 Tel Aviv Open, with Ilie Năstase; he also won the singles championship.

[6] Gilbert won a total of 20 top-level singles titles during his career including 1986 Pacific Coast Invitational against Aaron Krickstein,[7] and the biggest being the Cincinnati Masters tournament in 1989.

He was also runner-up in a further 20 singles events, including Cincinnati in 1990, where he lost to six-time Grand Slam champion Stefan Edberg, and the Paris Masters in 1987 and 1988.

Gilbert's most successful year on the tour was 1989, during which he won five singles titles, including Cincinnati, where he beat four future Hall of Famers to claim the title: Pete Sampras, Michael Chang, Boris Becker and Stefan Edberg.

[10] Unlike many other professional players of his era, Gilbert did not have a major offensive weapon such as an overpowering serve or forehand.

Although he was easy to get along with outside the court, Gilbert was a fierce competitor with a sometimes annoying style of play, focusing on his opponent's weaknesses.

The title of Gilbert's 1994 nonfiction book, Winning Ugly, was a self-deprecating nod to his unorthodox but successful tennis career.

[12] Gilbert won a bronze medal in men's singles at the 1988 Summer Olympics in Seoul.

On July 26, 2006, Gilbert was announced as taking over the coaching duties of Scottish player Andy Murray.

[22] Roger Draper, the LTA's chief executive, said: "We have set Brad a new challenge of getting Alex into the top 100 and also 'upskilling' our coaches and inspiring the next generation to follow in Andy's footsteps.

"[23] While still being committed to his TV items,[24] in December 2010 it was announced that Gilbert would return to coaching, and partner with Kei Nishikori of Japan for 15 tournaments in the 2011 season.