After retirement, Cheeks spent one year coaching for the
Continental Basketball Association’s
Quad City Thunder, before becoming the 76ers assistant coach in 1994 through 2001. He coached under head coaches
John Lucas (1994–96),
Johnny Davis (1996–97), and
Larry Brown, and he was an instrumental part of the Philadelphia team that reached the
2001 NBA Finals. In 2001, he was hired as Portland Trail Blazers head coach. He led the team to two playoff berths in four years as coach, but could not get past the first round. He was fired after a poor start to the 2004–05 campaign. On April 25, 2003, during a game between the Trail Blazers and the
Dallas Mavericks, Cheeks famously aided 13-year-old Natalie Gilbert in singing the
American national anthem. After Gilbert forgot the words at "At the twilight's last gleaming," Cheeks rushed over to help her, and they finished it together as the entire Rose Garden Arena crowd sang with them. Cheeks and Gilbert received a standing ovation after the song was over. Cheeks actions were used by
Harvard Business School Professor Thomas J. DeLong as an example of true leadership in times of crisis. Former 76ers general manager
Pat Williams called it "'just a beautiful moment of ... humanity.'" In 2005, Cheeks was named as head coach of the 76ers. However, he missed the playoffs in each of his first two seasons. Toward the end of the 2006 season, the two were fined for tardiness coming to a game, but soon apologized profusely to Cheeks. During the 2006–07 season, Iverson would be traded to the Nuggets and Webber would be released, leaving Cheeks with one of the youngest teams in the NBA. On February 20, 2007, the 76ers extended Cheeks' contract one year despite his losing record as coach. At the beginning of the 2007–08 season, expectations were low and the 76ers were picked to finish last in the Conference by many prognosticators. However, the Sixers clinched a playoff berth with a win over the Atlanta Hawks on April 4, 2008. It was their first postseason appearance since 2005, as well as the first in the post-Iverson era. However, they were eliminated by the
Detroit Pistons, 4–2. Even with this elimination, many fans considered this to be a successful season, considering that the 76ers were 12 games under .500 in early February and went on to have a 21–7 run that led them to the playoffs. The 76ers extended Cheeks' contract before the 2008-2009 season to 2010. They started out the 2008–09 NBA season 9–14 despite their signing of
Elton Brand and re-signing of
Andre Iguodala during the off-season. Due to their slow start, the 76ers fired Cheeks on December 13, 2008. On June 10, 2013, Cheeks agreed to become the head coach of the Detroit Pistons. On February 9, 2014, the Detroit Pistons relieved him of his head coaching duties and replaced him with
John Loyer on an interim basis for the remainder of the season. The move came after owner
Tom Gores suggested that the Pistons were "better than our record" and weren't playing "at their maximum"—a veiled criticism of Cheeks. On June 29, 2015, Cheeks returned to the Thunder as an assistant coach. On November 14, 2020, Cheeks was hired by the Chicago Bulls as an assistant coach following the team's hiring of
Billy Donovan. On June 13, 2024, it was reported that
Tom Thibodeau was hiring Cheeks to be an assistant coach for the
New York Knicks, and Cheeks joined the Knicks coaching staff for the 2024-2025 season. ==Honors and awards==