A casual trip to Canada Olympic Park left an indelible mark on Montgomery when he witnessed a skeleton race and immediately fell in love with the sport. Shortly thereafter, he began competing competitively and enjoying quick success.
Montgomery’s start to his rookie season on the World Cup could not have been drawn more perfectly. He kicked off his campaign with a bronze-medal finish on his home track in Calgary. He went on to finish in the top ten three more times during the season, finishing sixth overall in the World Cup standings. His sophomore season was equally remarkable. He achieved five podium finishes, including his first World Cup victory and a silver medal at the World Championships. He placed second overall on the World Cup, and from there he went on to win his first Olympic gold medal at the Vancouver 2010 Winter Olympics.
Since 2013, Montgomery has acted as the host of the hit television program The Amazing Race Canada, which sees teams of contestants competing with one another as they race to travel the country.