Cunningham was born in Arlington, Texas to Carrie and Keith Cunningham. He grew up playing football as a quarterback, which he claims helped become a better passer and leader on the basketball court. Cunningham focused on basketball after watching his brother play the sport in college. He frequently played basketball with his father and brother at a recreation center. In eighth grade, Cunningham played point guard for Barnett Junior High School in Arlington.
High school career
Cunningham attended Bowie High School in Arlington. Soon into his freshman season, he became a starter on the varsity team. Cunningham averaged 15.2 points, 6.4 rebounds and three assists per game, helping Bowie reach the District 6A Region I final, and was named District 4-6A Newcomer of the Year. In December 2017, early in his sophomore season, he suffered an injury while attempting to dunk at a tournament in Houston. Cunningham finished the season averaging 18.8 points, 8.2 rebounds, and 5.3 assists per game. He was named District 4-6A co-most valuable player and earned Texas Association of Basketball Coaches All-Region honors. In the summer prior to his junior year, Cunningham transferred to Montverde Academy, a school in Montverde, Florida with a successful basketball program. He chose Montverde Academy, whose team was ranked No. 1 in the country by USA Today, for its academics and coaching. On February 2, 2019, Cunningham recorded 26 points, nine assists, and seven rebounds in a 76–51 win over Oak Hill Academy, one of the top high school teams nationally, at the National Hoopfest tournament. At the end of his junior season, after averaging 11.4 points, 5.7 rebounds and 5.5 assists per game, he made the MaxPreps Junior All-American second team. In the summer of 2019, Cunningham was named Nike Elite Youth Basketball Leaguemost valuable player after averaging 25.1 points, 6.6 rebounds, and 5.2 assists per game for the Texas Titans in the EYBL regular season. For his senior season at Montverde, he was joined by many more top recruits, including five-star forwards Scottie Barnes and Day'Ron Sharpe. Many analysts regarded his team as one of the best in high school basketball history. Cunningham averaged 13.9 points, 6.4 assists and 4.2 rebounds per game, leading Montverde to a 25–0 record with an average margin of victory of 39 points. He played only 22 minutes per game due to the depth of his team, which often dominated its opposition. At the end of the season, he was honored as Naismith Prep Player of the Year and MaxPreps National Player of the Year. Cunningham was selected to play in the McDonald's All-American Game, Jordan Brand Classic and Nike Hoop Summit, but all three games were canceled due to the coronavirus pandemic.
Recruiting
Cunningham emerged as a top 25 recruit in the 2020 class at the end of his sophomore season at Bowie. He is a consensus five-star recruit and one of the best players in his class. Cunningham received offers from top NCAA Division I programs, including Duke, Kentucky and North Carolina, but many analysts viewed Oklahoma State as his likely destination after the program hired his brother, Cannen, as an assistant coach. On November 5, 2019, Cunningham announced his commitment to Oklahoma State. He became the highest-ranked commit in program history and the first five-star recruit to join Oklahoma State since Marcus Smart in 2012. In June 2020, the NCAA imposed a postseason ban on Oklahoma State, however Cunningham announced on June 22 that he was still attending Oklahoma State rather than sign with another school or the NBA G League.
National team career
Cunningham played for the United States at the 2019 FIBA Under-19 World Cup in Heraklion, Greece. In seven games, he averaged 11.7 points, 5.7 assists and 4.9 rebounds per game, helping his team win the gold medal. In the finals, Cunningham led all scorers with 21 points, seven rebounds, and seven assists in a 93–79 win over Mali.
Personal life
Cunningham's father Keith Cunningham played college football for Texas Tech. His older brother Cannen played college basketball for SMU, surpassing the school record for games played, before spending one professional season in Poland. Cannen later pursued a coaching career, becoming an assistant coach for Oklahoma State entering the 2019–20 season.
