As a player Brad Gilbert was one of the sport’s top strategists, a fierce competitor whose mental approach and style of play outwitted some of the greatest players in the world during a 13-year pro career.

The Californian ranked a career-high No. 4 (1 January 1990) in singles, capturing 20 titles from 40 finals. He won a singles bronze medal at the 1988 Olympic Games in Seoul, when he lost to American compatriot Tim Mayotte 6-4, 6-4, 6-3. He also reached two Grand Slam quarter-finals at the 1987 US Open (l. to Connors) and 1990 Wimbledon (l. to Becker), and finished runner-up at the inaugural Grand Slam Cup in 1990 (l. to Sampras). He represented United States in Davis Cup from 1986-1993, compiling a 10-5 overall record.

Gilbert had his best season as a pro in 1989, after undergoing left ankle surgery in April 1988. The right-hander won 20 of 21 matches, including a 17-match winning streak during the North American hard-court swing, winning three straight tournaments from four finals. In the build-up to the US Open at Cincinnati, he beat No. 6 Michael Chang, No. 2 Boris Becker and No. 3 Stefan Edberg in succession to win the title. He closed the year by winning his fifth title at San Francisco (d. Jarryd), finishing with a 60-17 match record and $900,848 in prize money.

Gilbert compiled a 27-64 lifetime record against Top 10 opponents, with arguably his most significant victory over World No. 2 John McEnroe at the Nabisco Masters in New York, in January 1986, when he beat his American compatriot 5-7, 6-4, 6-1. It was McEnroe's only loss to Gilbert in 13 matches and that defeat drove the New Yorker from the sport for six months. "I'm not going to play tennis if I lose to jerks like that," said McEnroe after the loss. Gilbert would later recount the incident in his 1994 best-selling book, Winning Ugly: Mental Warfare in Tennis – Lessons from a Master, which gives tips on how you can beat players who have been beating you. It is one of the best-selling tennis books of all time.

Oakland-born Gilbert started playing tennis aged five. His sister Dana played on the WTA Tour and his older brother, Barry, played at the University of South Carolina. Gilbert won the U.S. Amateur Hard Court Championship, while studying at Foothill College in Los Altos, California from 1980-82. He was a member of the United States junior Davis Cup team in 1981 and became an All-American and reached the 1982 NCAA Championship at Pepperdine University. He turned pro after his junior year.

Gilbert retired as a player in 1994 and has since established himself as one of the world’s leading coaches and analysts. He coached Andre Agassi (1994-2002), who described Gilbert as “the greatest coach of all time”, to six Grand Slam titles. Tony Roche coached Ivan Lendl to the same number of major titles in the 1980s. He helped Andy Roddick to the 2003 US Open title and year-end No. 1 ranking. In 2006 he teamed up with Andy Murray, helping him to a No. 8 ranking in a 16-month partnership, and also helped other British players until 2009.

He now works as a television analyst for ESPN, and resides in San Rafael, California, with his wife, Kim, and their three children. An avid sports fan, he follows the Oakland Raiders in American football, the Oakland Athletics in baseball and Golden State Warriors in basketball. Bio: James Buddell

(September 2014)