The Toronto native grew up skiing out of the Georgian Peaks Ski Club and later moved to Whistler during the winters where he started his FIS career. Jack Crawford made the Development Team in  2015-16 and after an exceptional season of Nor-Am Cup podium success, he qualified for the National Team. By 19-years-old, Crawford has already competed in Europa Cups and made his World Cup super-G debut on the Kitzbuehel track, making him a promising speed skier. In the 2015-16 season, Crawford also competed in the World Junior Championships in Sochi where he was consistently placed in the top five with his top result being second-place in the super-G. In the 2016-17 season, Crawford made another strong appearance at the World Junior Championships in Äre, SWE where he secured two fourth-place finishes. Crawford had his first downhill World Cup start in the 2017-18 season and attended his first Olympic Games where he raced the alpine combined, super-G and giant slalom.