Because of his father's multi-decade career as an NBA referee, Crawford has been exposed to basketball at a high level from an early age.

[6] On March 9, 2010, he was named Big Ten Freshman of the Year by the media (D. J. Richardson earned the same honor from the coaches).

That season, he was an honorable mention 2009–10 All-Big Ten performer and one of three unanimous All-Freshman selections (along with Richardson and Christian Watford).

[10] On March 11, he posted his third career double-double against Ohio State in the 2011 Big Ten Conference men's basketball tournament.

[18] The following year as a redshirt senior, Crawford began the season as the Big Ten active career scoring leader.

[20] On January 29, Crawford posted 30 points and 8 rebounds to lead Northwestern to a 65–56 victory over (#14 AP Poll/#13 Coaches' Poll)[21] Wisconsin.

[24] The following day, he was recognized as the Oscar Robertson National Player of the Week by the United States Basketball Writers Association.

[41] Crawford signed with Barangay Ginebra San Miguel of the Philippine Basketball Association on June 2, 2016,[42] but he backed out in order to attempt to pursue the NBA Summer League.

[47] On August 7, 2017, Crawford returned to Israel for a second stint, signing a one-year deal with Maccabi Rishon LeZion.

[48] On November 18, 2017, Crawford recorded a season-high 32 points, shooting 11-of-15 from the field, along with 4 rebounds in a 92–88 win over Ironi Nahariya.

[51] On May 25, 2019, Crawford recorded a career-high 33 points, shooting 13–21 from the field, along with six rebounds and three assists in an 81–78 playoff win over Pallacanestro Trieste.

On January 27, 2020, Crawford returned to Italy for a second stint, signing with Olimpia Milano for the rest of the EuroLeague season.