Born in a rough inner city neighborhood in north St. Louis and never getting to meet his father, Carrawell attended high school at Cardinal Ritter College Prep in St. Louis. Among his teammates were future NBA players Loren Woods and Jahidi White. In four years on the Cardinal Ritter varsity, he led the team to an overall 80-13 record, including a three-year undefeated streak at home. Carrawell was a USA today Top 40 All American going into his junior season, where he averaged 20.6 points per game as Cardinal Ritter won the state's Class AA championship. The following season, Cardinal Ritter defended its state title. Carrawell again led the team, averaging 17 points and 8 rebounds per game. Carrawell was named conference Player of the Year twice, earned Central Region honors as Gatorade Player of the Year, and was a fourth-team Parade All-American. He set school career records for points, rebounds, and assists. Cardinal Ritter made USA Today's list of the top 25 high school teams in the country twice during Carrawell's prep career.