Bolger started the US Super Tour for the first time in Craftsbury in March 2012 and came 51st place over 3 km freestyle. In January 2017, he became the US American sprint champion in Soldier Hollow , which was his first victory in the US Super Tour. In the 2017/18 season he took second place in the sprint of the US Super Tour in Anchorage and third in the 10 km freestyle and sprint in Craftsbury. In February 2018 he won the sprint in Ishpeming , where he also finished third in the 10 km freestyle and second in the mass start over 20 km freestyle. Based on these results, he made his debut in the World Cup in Lahti in early March 2018 . He got his first World Cup points with 11th place in the sprint. At the end of the season he finished 60th in the World Cup finals in Falun and came second in the overall ranking of the US Super Tour. In the 2018/19 season he finished 59th in the Lillehammer Triple and 44th in the World Cup final in Québec . At the season highlight, the Nordic World Ski Championships 2019 in Seefeld in Tirol , he finished 18th in the sprint.