Montgomery started skeleton racing when he lived in Calgary where he worked as an auctioneer not far from Canada Olympic Park in Calgary. Sometime in 2002 he visited the track with his parents where a skeleton race was being held. He was immediately hooked on the sport and soon started racing competitively. Initially he did not do well in his first two seasons competing on the World Cup tour. However, he won his first World Cup race in Cesana, Italy, in 2008. He won two silver medals at the 2008 FIBT World Championships in Altenberg, Germany, in the men's skeleton and mixed bobsleigh bobsleigh-skeleton team event. His highest World Cup overall placing came when he finished second overall in the 2007–08 Skeleton World Cup.
Montgomery qualified for the 2010 Winter Olympics in Vancouver based on his results in the 2009-10 Skeleton World Cup. In the Olympic event he trailed Martins Dukurs after the first run but established the fastest times the following two runs, including a track record 52.20 on his third run. In the fourth and final run, on February 19, 2010, Montgomery still trailed Dukurs by 0.18 seconds, but Dukurs was 0.25 seconds slower on his final run. Thus Montgomery won the gold medal by 0.07 seconds. He celebrated exuberantly at first but quickly apologised to Dukurs for his celebration. He was quoted as saying after the race, "I had said at the beginning of the race that if I was in that position and I did get gold coming from behind that I was going to remain stoic and respectful because you never want to cheer when somebody else loses. But I have to apologize to Martins. That didn't happen. I lost my mind when I saw the .07 come up. It was like I had stuck my finger in a light socket." He accepted his gold medal at the medal ceremony in Whistler on February 20, 2010. Montgomery became the second Canadian in a row to win gold in the men's event, after Duff Gibson in 2006.

Following his win, Montgomery marched through a crowd of Canadian fans singing the national anthem and chugging a pitcher of beer. Writing in 2020, Montgomery explained the significance of the moment: .mw-parser-output .templatequote{overflow:hidden;margin:1em 0;padding:0 40px}.mw-parser-output .templatequote .templatequotecite{line-height:1.5em;text-align:left;padding-left:1.6em;margin-top:0}

Return to Jon Montgomery Autograph Profile