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On September 5, 2018, it was announced that Gamble was resigning from CMU to take a scouting position with the Toronto Raptors.

In April 2012, Gamble joined Davis to be an assistant coach at Central Michigan.

In June 2010, Gamble resigned as head coach of the University of Illinois at Springfield to become the Director of Player Development and Video Operations for Providence College under head coach Keno Davis, whose father Tom Davis formerly coached Gamble at Iowa.

In 2002, Gamble was named the first head men's basketball coach at the University of Illinois at Springfield (UIS), who began play in the American Midwest Conference of the NAIA that season. In his fourth year at the helm, 2005–06, Gamble coached the Prairie Stars to an AMC Tournament championship and a berth in the NAIA National Tournament. The next season, 2006–07, saw the Prairie Stars capture their first AMC regular season title outright, win their second consecutive AMC Tournament and advance to the second round of the NAIA National Tournament. Gamble's team went 11–1 in conference play and 23–9 overall as his continued success earned Gamble his second AMC Coach of the Year honor. Two years later, in 2008–09, the team posted a 21–9 record in their final season of NAIA play. Beginning in 2009–10, the Prairie Stars joined the NCAA's Division II and the Great Lakes Valley Conference. Gamble's team posted an 11–13 record in their first year of NCAA competition.

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. He then saw his starting time drop dramatically in his final two seasons in Boston, playing in 75 games but starting only 29 in 1994. He was the last Celtic to wear #34 before Paul Pierce. 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. With the Kings, Gamble did not start a game for the remainder of the season. He returned in 1996–97 to play in 62 games and start two, but averaged only five points a game. He did not play for the Kings in 1997–98 and was released by the team on February 20, 1998.

After seeing spot duty for two seasons, Gamble assumed a major role with Boston in 1990–91. Gamble played in every game, including 76 starts, and averaged 15.6 points (fourth on the team, behind Bird, Reggie Lewis and Kevin McHale) in 33 minutes per game and helped the Celtics to a 56–26 record and a return to first place in the Atlantic Division. His 58.7% shooting percentage was third-best in the NBA. He also placed second to Scott Skiles of Orlando in the voting for the NBA Most Improved Player Award, the closest finish in the history of the award, with a winning margin of four votes. 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 71 games the following season, 1989–1990, averaging 5.1 points in 13.9 minutes-per-game.

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. His stint was followed by an invitation to the Detroit Pistons’ rookie camp the following summer, followed by a training camp tryout with the Milwaukee Bucks later that fall. Neither team ended up signing Gamble.

Gamble then played in the Philippines for a month, where he teamed with Billy Ray Bates in the 1988 PBA Reinforced Conference for Añejo Rum. In the four games he played with Anejo, he averaged near 50 ppg. However, with a losing record, Añejo management decided to send Bates and Gamble home.

In December 1988, one of those Hall of Famers, Larry Bird was injured. Gamble was called up from the CBA and was signed the remainder of the season. Gamble played sparingly the first few months after signing his contract (not playing in 17 games), however his playing time picked up at the end of the season, with Gamble scoring at least 15 points in the final six games and hitting a season-high with 31 in the regular season finale. Gamble played in one playoff game before going down with an injury; the Celtics were swept by the Detroit Pistons in the first round.

Gamble was selected with the 17th pick of the third round (63rd overall) by the Portland Trail Blazers in the 1987 NBA Draft. He only played in 19 minutes with Portland before being waived on December 9, 1987.

Under coach George Raveling Gamble played off the bench in his first season at Iowa. After the season, Raveling left Iowa for the University of Southern California. On April 7, 1986, Iowa named Tom Davis as its new head coach. Davis’ arrival reversed Gamble's fortunes, as he became a starter for Iowa in his senior season, and the team began the season with 17 straight wins to earn the #1 ranking in the AP Poll. In the Sweet Sixteen of the 1987 NCAA Men's Division I Basketball Tournament, Gamble hit the winning shot against the University of Oklahoma to send the Hawkeyes to the Elite Eight, where they faced the University of Nevada, Las Vegas. 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. Iowa finished with a 30–5 record.

Following high school, Gamble enrolled at Lincoln College in Illinois, where he played for two seasons under head coach Alan Pickering. After two seasons at Lincoln, Gamble transferred to the University of Iowa. He was part of a 1985 recruiting class which included B. J. Armstrong, Roy Marble, Les Jepsen and Ed Horton. All five recruits went on to play in the National Basketball Association. Horton and Gamble played together at Lanphier High School.

Gamble was born in Springfield, Illinois and lived in the city's John Hay public-housing projects with his single mother. Gamble entered Springfield's Lanphier High School; by his senior season, Gamble led the Lions to the 1983 Illinois Class AA State Basketball Championship. He scored 67 points in that season's four tournament games, which culminated with a 57-53 win over Peoria High School. Lanphier finished the 1983 season 30–3, while Gamble was the only Lanphier player selected to the All-Tournament team. In 2009 Gamble was named that year's inductee into the Lanphier Hall of Fame.

Kevin Douglas Gamble (born November 13, 1965) is a retired American professional basketball player in the National Basketball Association and currently a scout with the Toronto Raptors. At 6'5" (1.96 m) he played as both a shooting guard and small forward.