He played for the Boston Celtics during a period of nervous change, joining the club just as the Big Three was beginning to break down, its parts worn from too many minutes and too little rest, the post-Bias funk settling in like a fog, thick, heavy and unrelenting.  He played valiantly through the Jimmy Rodgers and Chris Ford Eras, which is to say that he competed during the slow decay of basketball’s greatest franchise, his sizeable contributions spilled in fruitless pursuit of the NBA’s greatest prize.  He was there as Larry Bird lay prone in front of the Celtic bench, Bird’s back so creaky that his greatness, routinely on display for more than a decade, could only be coaxed out between bouts with pain.  He was there for Larry Legend’s inevitable retirement, as he was for Kevin McHale’s farewell one season later.  He grieved through the tragic loss of Reggie Lewis, and he played through final days of the historic Boston Garden.  That Kevin Gamble – nicknamed Oscar by former teammate Danny Ainge – was able to do any of these things is simply amazing, especially for a player cut by two NBA franchises, passed on by the rest, and then forced to toil overseas.  That Gamble could resurrect his career in the satellite world of the Continental Basketball Association and then, against all odds, play six integral seasons with the Boston Celtics, is as much a testament to his perseverance and work ethic as it is to his high basketball IQ.

We’ve all heard this one before.  The sports world has no shortage of these stories, of athletes who overcome seemingly insurmountable odds to fulfill a dream, of players who refuse to believe that they’re not big enough, or fast enough, or strong enough to succeed in their chosen field of competition.  What makes Gamble’s story so special is not that he was able to prove the naysayers wrong, but that he was able to excel for so long after being written off by so many.  Gamble’s NBA career could have just as easily ended nine games into the 1987-88 regular season when, as a rookie, he was cut by the Portland Trailblazers to make room for veteran backcourt talent.  Instead, Gamble resurfaced in Boston on December 18th, 1988, taking the circuitous route back to the NBA while breathing life into a career that would last for ten seasons.

Such resolve gets instilled at an early age, and Gamble was fortunate to have parents who preached the value of a strong work ethic.  They kept Gamble focused, both on the court and in the classroom, and he responded with the same steady, workmanlike dedication that would later serve him so well in the NBA.  He entered Springfield's Lanphier High just hoping to make the team, but by his senior season Gamble was the star, leading the Lions to the 1983 Illinois Class AA State Basketball Championship.  Gamble scored 67 points in those four tournament games, which culminated with a 57-53 win over Peoria High School.  Lanphier finished the ’83 season 30-3, with Gamble was the only Lanphier player selected to the All-Tournament team.

While few questioned Gamble's ability at the high school level, many college recruiters wondered whether he possessed legitimate Division I basketball potential.  Gamble believed otherwise.  He was 6’7” with a quick first step and decent range.  He was strong enough to compete beneath the basket, yet fast enough to play the wing.  He felt confident that he could play at the Division I level.  The major colleges, however, weren’t biting; there was tepid interest at best, courtesy inquiries for the most part, with little in the way of scholarship offers.  Undeterred, Gamble enrolled at Lincoln Junior College, where he played for two seasons under the guidance and tutelage of head coach Alan Pickering.  It was the first of many side-stops on his long journey to the NBA, but Gamble spent the time wisely.  He understood that his game needed work, especially on the defensive end of the court, and that Pickering had a reputation for tough, hard-nosed defense.  For his part, Pickering understood that Gamble’s game was only in need of refinement, and that the right amount of focus would put him on solid footing at the next level.

After two seasons under Lincoln’s sage coach, Gamble was indeed ready for primetime.  He transferred to the University of Iowa, where he ran into yet another obstacle on his road to the NBA:  Then-head coach George Raveling’s persistent lack of faith in Gamble as a defender.  Unconvinced that Gamble was prepared to fit his system, Raveling kept the junior college transfer pinned to the bench for much of the season.  Gamble questioned his coach but kept it largely to himself; he was young, yet mature enough to understand that such grousing would only make the situation worse.  And then, as if by divine intervention, Raveling bolted the Iowa program to take the head coaching job at USC.  On April 7, 1986, Iowa named Tom Davis as its new head coach.  A native of Ridgeway, Wisconsin, the 46-year-old Davis had coached at high schools in Wisconsin and Illinois from 1960-1966, and was an assistant coach at American University for two years before becoming the head coach at Lafayette.

Davis’ arrival breathed new life into Gamble’s collegiate career.  Given a clean slate, the Springfield product became a key starter for the Hawkeyes, as the team raced to a 17-0 start and the Number 1 ranking in the Associated Press poll.  Iowa finished 30-5 before falling in the NCAA Regional Finals, and Gamble’s play was at the center of it all.  From an NBA standpoint, it helped that he played bigger with the stakes the highest.  Scouts took notice of his tournament play, with the Portland Trailblazers selecting him in the third round of the 1987 NBA Draft.