He was named to several prominent high school All-America teams as a senior, including being selected to play in the 2011 McDonald's All-American Game[2] and the Jordan Brand Classic.

[5] In his final collegiate game, he scored a career-high 32 points and 13 rebounds in a loss against LSU at the SEC tournament in Nashville.

He later joined the Pistons for the 2013 NBA Summer League and signed his rookie scale contract with the team on July 19.

[9] In July 2014, Caldwell-Pope rejoined the Pistons for the 2014 NBA Summer League, where he averaged 24 points and 7.4 rebounds in five games.

Head coach Stan Van Gundy quickly assessed Caldwell-Pope as his best perimeter defender and he wound up leading the Pistons in minutes played with 2,587.

[11] He helped the Pistons finish the 2015–16 regular season with a 44–38 record, which was good for the eighth seed in the Eastern Conference.

In the first round of the playoffs, the Pistons faced the first-seeded Cleveland Cavaliers, and in a Game 1 loss on April 17, Caldwell-Pope scored a team-high 21 points.

[14] On January 8, 2017, he hit a three-pointer with 9.4 seconds left in double overtime to lead the Pistons to a 125–124 win over the Portland Trail Blazers; he finished with 26 points.

[16] On February 23, 2017, Caldwell-Pope scored 33 points, including three three-pointers late in the fourth quarter during a Detroit rally, as the Pistons defeated the Charlotte Hornets 114–108 in overtime.

[17] On June 23, 2017, Caldwell-Pope was suspended for two games without pay by the NBA for pleading guilty to operating a motor vehicle while intoxicated.

He was handed a 25-day jail sentence, but under a work-release program, was allowed to leave the facility for home games and practices.

On July 6, 2022, Caldwell-Pope was traded, alongside Ish Smith, to the Denver Nuggets in exchange for Monté Morris and Will Barton.

[38][39] He made his Nuggets debut on October 19, recording two points, four rebounds, six assists and two steals in a 123–102 loss to the Utah Jazz.

[40] In Game 5 of the NBA Finals, Caldwell-Pope put up 11 points, four rebounds, two assists, two steals, three blocks and grabbed the series-clinching rebound before dribbling out the final seconds on the clock in a 94–89 win over the Miami Heat to help the Nuggets win their first NBA championship in franchise history, awarding Caldwell-Pope his second ring.