Wilson mainly took part in the Nor-Am Cup from 2005 to 2011. It took second place in the Moguls discipline in the winters 2009/10 and 2010/11. In the World Cup he made his debut at the beginning of the 2011/12 season in Ruka and finished ninth in the Moguls. In the further course of the season he made it seven times in the top ten and thus reached seventh place in the Moguls discipline. At the Junior World Championships 2012 in Chiesa in Valmalenco , he won gold in the Moguls.
In the following season 2012/13 Wilson reached his first World Cup podium finish in Deer Valley with third place in the Dual Moguls. At the World Cup in Inawashiro he took second place in the Moguls and one day later he won his first World Cup victory in the Dual Moguls competition. At the Freestyle Skiing World Championships in 2013 in Voss , he finished 22nd in the Dual Moguls and eighth in the Moguls. At the end of the season he came in third place in the dual moguls in Åre and finished the season in 14th place in the overall World Cup and fourth place in the Moguls discipline. At the national championships in Heavenly in 2013 , he was American champion in the Mogul discipline.
In the 2013/14 season Wilson won third place in the World Cup in Lake Placid , Val St. Come and Voss . In Inawashiro he achieved the second World Cup victory in the Moguls competition. In his first Olympic participation in Sochi in 2014 , he came 20th in the Moguls. As in the previous year, he finished the season in 14th place in the overall World Cup and fourth in the Moguls discipline. At the end of March 2014, he became the American master in dual moguls and runner-up in the moguls in Deer Valley .
Wilson won his first World Cup appearance after almost a two-year break in competition in February 2016 in Tazawako in the Moguls and the following month at the US Championships in the Dual Moguls. In the 2016/17 season he finished in the top ten four times in the World Cup, including third place in the Dual Moguls in Thaiwoo ; so he reached seventh place in the Mughal World Cup. At the 2017 World Championships in Sierra Nevada , he won the silver medal in the Dual Moguls, and was fifth in the Moguls competition. In the following season he achieved five top ten finishes, including two third places, eighth place in the Moguls World Cup. At the season highlight, the 2018 Winter Olympics in Pyeongchang , he came in 18th. In March 2018, he became the American Moguls and Dual Moguls Masters. In the 2018/19 season he came in six places in the top ten, including third place in the Moguls in Tazawako, and seventh place in the Moguls World Cup. Another dual moguls silver medal was added at the 2019 World Championships in Park City .