Gamble was born in Springfield, Illinois and lived in the city's John Hay public-housing projects with his single mother.

[2] Following high school, Gamble enrolled at Lincoln College in Illinois, where he played for two seasons under head coach Alan Pickering.

He was part of a 1985 recruiting class which included B. J. Armstrong, Roy Marble, Les Jepsen and Ed Horton.

Against UNLV, Gamble attempted a 3-pointer as time expired, but the shot bounced off the rim, ending what was arguably Tom Davis's most successful season at Iowa.

[3] Gamble then headed to the Continental Basketball Association for the Quad City Thunder, where he averaged 21.1 points per game (ppg) with the team in 1988.

[6] In his debut start with the Celtics, a 113–104 win over the Cleveland Cavaliers on April 14, 1989, Gamble had a double-double with 20 points and 10 assists, in addition to grabbing seven rebounds.

Gamble's minutes were cut dramatically in the playoffs and he averaged just six points per game against the Indiana Pacers and Detroit Pistons.

Gamble played in all 82 games the next season, starting 77 of them, but the Celtics were eliminated by the Cleveland Cavaliers in the second round of the playoffs.

Following the season, Gamble signed a free agent contract with the Miami Heat, playing in 44 games (starting 13) before a late February 1996 trade sent him to the Sacramento Kings.

In 2002, Gamble was named the first head men's basketball coach at the University of Illinois Springfield (UIS), who began play in the American Midwest Conference of the NAIA that season.

Beginning in 2009–10, the Prairie Stars joined the NCAA's Division II and the Great Lakes Valley Conference.