Crawford attended La Salle High School in Cincinnati, Ohio, who he led to a 23–3 record as a senior, including a 9–1 mark in the Greater Catholic League (GCL).

[1] After graduating from high school, Crawford played for Bowling Green where he was an All-MAC conference player as a senior after averaging 15 points, 4 assist, 3 rebounds and 2 steals per game.

[1][2] In September 2014, Crawford signed with the Halifax Rainmen of the Canadian NBL,[2] but later left the team before appearing in a game for them.

[7] Three days later, he made his debut in a 120–109 win over the Fort Wayne Mad Ants, recording three points, one rebound and one assist in 16 minutes off the bench.

[8] Crawford played for Águilas Doradas de Durango in the Mexican CIBACOPA in 2017 and then joined the Memphis Hustle for the 2017–18 NBA G League season.

[14] He helped the JackJumpers win the NBL championship with a 3–2 grand final series victory over Melbourne United.