In his 20s, Wilson began noticing his gait changing and he would constantly be rolling his ankles.[2] He was eventually diagnosed with Charcot–Marie–Tooth disease, a neurological condition that affected his nerves and muscles. After losing over 100 pounds, he bought himself a bike to stay active and continue to lose weight.[3] He subsequently joined the Juventus Cycling Club in 2012 where he met coach Cam Jennings.[4] By 2014, he joined the Argyll Velodrome Association and raced in the 2014 UCI Para-cycling Road World Championships.[5]
While training for the 2015 UCI Para-cycling Road World Championships, Wilson was struck by a car backing out of a parking spot. As his body flew through the back window, he broke his clavicle, some ribs, and vertebrae.[6] However, he recovered by 2016 and was named to Team Canada's roster for the 2016 Summer Paralympics.[7] To qualify for the Paralympics, Wilson set a new world and Paralympic record at 3:53.66, which was beaten five minutes later by Zhangyu at 3:50.373.[8] Wilson ended his first Paralympic Games with two silver medals; one in men’s c1 individual pursuit and another in the men’s c1 road time trial.[9]