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Cheaney played small forward for the Indiana University Hoosiers for head coach Bob Knight. He was Knight's first left-handed player. Cheaney was known as a smooth leader all four years at Indiana. During the last three of his years at Indiana, the team spent all but two of the 53 poll weeks in the top 10, and 38 of them in the top 5. The Hoosiers were 87–16 (.845) those years and a 46–8 (.852) mark in the Big Ten Conference. Of the four years Cheaney played the Hoosiers went 105-27 and captured two Big Ten crowns ('91 and '93). The 105 games won during Cheaney's four years was the most of any Hoosier to that point.

On August 21, 2013, Cheaney announced that he had accepted an assistant coach position at Saint Louis University under head coach Jim Crews, a fellow alumnus of Indiana University. During his first season with St. Louis in 2013–14 the Billikens finished with a 27–7 record and secured an Atlantic 10 Conference regular-season title and an NCAA Tournament appearance. Cheaney left the St. Louis staff in 2016 with the departure of Crews as head coach.

Following his retirement as a player, Cheaney spent two seasons on the staff for the Golden State Warriors. He was a special assistant in the front office in 2009–10, and in 2010–11 he was an assistant coach under fellow Indiana alumnus Keith Smart. He then returned to Indiana in 2011 and served as Director of Basketball Operations under coach Tom Crean. The following year he added the title of Director of Internal and External Player Development.

Cheaney appeared along with many of his 1997 Bullet teammates (Juwan Howard, Ben Wallace, and Ashraf Amaya) in singer Crystal Waters' 1996 video "Say If You Feel Alright". He also appeared in the 1994 film Blue Chips as a player for the Indiana University Hoosiers.

Cheaney was selected 6th overall by the Washington Bullets in the 1993 NBA draft. His strongest showing as pro came in 1994–1995 when he averaged a career-high 16.6 points for Washington. He spent six years playing for the Bullets/Wizards (including a playoff appearance in 1997). He would go on to play for the Boston Celtics, Denver Nuggets, and Utah Jazz, before closing his career out with three years with the Golden State Warriors, retiring after the 2005–06 season. During his thirteen-year NBA career, Cheaney played for five different teams, averaging 9.5 points and 3.2 rebounds.

As a senior during the 1992–93 season, Cheaney averaged 22.4 points per game and 6.2 rebounds per game. The Hoosiers finished the regular season with an overall record of 31–4 and a conference record of 17–1, finishing 1st in the Big Ten Conference. As the Big Ten Conference Champions, the Hoosiers were invited to participate in the 1993 NCAA Tournament as a 1-seed, where they advanced to the Elite Eight for the second year in a row, but were defeated by Kansas.

As a junior during the 1991–92 season, Cheaney felt he struggled from being worn down by substantial play over the summer. Moreover, with the addition of other talent from players like Alan Henderson, Cheaney "didn’t have to score as much." He regressed to an average of 17.6 points per game and his three-point shooting percentage dropped significantly. The Hoosiers finished the regular season with an overall record of 27–7 and a conference record of 14–4, finishing 2nd in the Big Ten Conference. The Hoosiers were invited to participate in the 1992 NCAA Tournament as a 2-seed, where they advanced to the Final Four, but fell to Duke in a foul-plagued game in Minneapolis.

Cheaney averaged 21.6 points per game as a sophomore, with the Hoosiers ending the 1990–91 regular season with an overall record of 29–5 and a conference record of 15–3, finishing 1st in the Big Ten Conference. As conference champions, the Hoosiers were invited to participate in the 1991 NCAA Tournament as a 2-seed, where they advanced to the Sweet Sixteen. Cheaney noted, “I had a very good sophomore year, but I played a lot of international ball. I played on the Tournament of America team and the World University team. I think I wore myself out a little bit, and when my junior year rolled around, I wasn’t up to par.”

Born in Evansville, Indiana, Cheaney played high school ball at William Henry Harrison High School in Evansville and was selected to the 1989 Indiana All-Star team. Cheaney was a high school stand-out, but a season-ending injury midway through his senior year pushed him off the national radar and left him as a virtual unknown in Indiana University's #1 ranked recruiting class of 1989.

Cheaney began his career with a flash, scoring 20 points in the season opener of his freshman year (the only Indiana freshman to ever do so). However, the 1989–90 team ran into tougher competition in January after winning all 10 of their pre-conference games. Taken aback by the intensity of play within the Big Ten, the young Hoosier squad went 8–10 in conference play and were upset by California in their NCAA Tournament opening game. Cheaney averaged 17 points a game as a freshman.

Calbert Nathaniel Cheaney (born July 17, 1971) is an American basketball coach and former player who is an assistant coach for the College Park Skyhawks of the NBA G League. He starred as a player for the Indiana Hoosiers from 1989–93 under coach Bob Knight. Cheaney ended his career as a three-time All-American and remains the Big Ten's all-time leading scorer with 2,613 career points. He led Indiana to a 105–27 record and the NCAA Tournament all four years, including a Final Four appearance in 1992.