Crawford comes from Toronto and moved in his youth to Whistler in the province of British Columbia , in order to advance his career. As a 16-year-old, he took part in FIS races from December 2013 and was able to celebrate a victory in Panorama on his second outing. In February 2014 he became the Canadian junior giant slalom champion . On March 11, 2014, he made his debut in the Nor-Am Cup , with 14th place in the giant slalom in Nakiska straight away in the points. The first podium in the Nor-Am Cup was achieved by Crawford on December 17, 2015 (2nd place in the slalom of Panorama), the first victory on February 12, 2016 in the combination on Whiteface Mountain . At the Junior World Championships in Sochi in 2016 , he won the silver medal in the Super-G. In the 2015/16 Nor-Am Cup , he finished second in the overall ranking and third in the Super-G ranking.
Crawford started the World Cup for the first time on January 22nd, 2016, although he did not finish in the Super-G on the Streif in Kitzbühel . In the 2016/17 Nor-Am Cup , he achieved three podium places, making him second in the Super-G and third in the overall standings. At the 2016 Junior World Championships in Åre , he won the gold medal in the team competition , plus two fourth places. Due to consistently good performances, he was nominated for the 2018 Winter Olympics in Pyeongchang ; there he finished 20th in the combination and 29th in the giant slalom. Towards the end of the season he won the 2017/18 Nor-Am Cup four times ; so he decided the downhill and super-G classification for himself, while he missed victory in the overall classification by only six points.
Crawford scored his first World Cup points on November 25th, 2018 with 27th place in the Super-G of Lake Louise .