Caldwell started in Rumford in January 2011 for the first time in the US Super Tour and finished 75th over 15 km classic and 66th place in the sprint. At the 2012 Winter Youth Olympic Games in Innsbruck , he won the bronze medal in the mixed relay. He also achieved 16th place over 10 km classic and fifth place in the sprint. His best results at the Nordic Junior World Ski Championships in 2014 in Fiemme Valley were 12th place in the relay and tenth place in the skiathlon . At the U23 World Championships 2015 in Almaty , he came 20th in the skiathlon and 15th in the 15 km freestyle. In the 2015/16 season he won his first victory in the US Super Tour in Craftsbury over 10 km freestyle. He also took third place there over 15 km freestyle and reached 11th place in the overall ranking of the US Super Tour at the end of the season. At the U23 World Championships in 2016 in Râșnov , he achieved 43rd place in the sprint, 27th place over 15 km classic and 21st place over 15 km freestyle. The following year he finished 18th in the sprint and ninth place over 15 km freestyle and skiathlon at the 2017 U23 World Championships in Soldier Hollow . In March 2017, he made his debut in Québec in the cross-country skiing world cup . There he got his first World Cup points in the World Cup final , which he finished in 46th place, and in the final stage with 25th place. At the end of the season he finished second in the overall ranking of the US Supertour with two second places. After finishing 51st in the Ruka Triple at the beginning of the 2017/18 season, he finished 38th in the Tour de Ski 2017/18 . He got his only World Cup points of the season in the final stage in Fiemme Valley with 22nd place and in Ruka with 19th place. At the 2018 Winter Olympics in Pyeongchang , he finished 51st in the skiathlon. He finished the World Cup final in Falun in 59th place.
United States