Jon Montgomery

Early life and introduction to skeleton

Jon Montgomery was born on May 6, 1979, and grew up in Russell, Manitoba. He was inspired by fellow Russell native and NHL star Theoren Fleury, who demonstrated that athletes from small towns could achieve greatness. Montgomery's path to the Olympics was not a direct one. After high school, he attended the Canadian Automotive Institute, now the Automotive Business School of Canada at Georgian College, and worked as an automobile auctioneer and sales consultant in Calgary. His athletic destiny was sparked in 2002 when, during a visit to Canada Olympic Park in Calgary with his parents, he witnessed a skeleton race for the first time. He was immediately hooked on the sport and enrolled in a Discover Skeleton school shortly thereafter, quickly transitioning from curious spectator to dedicated athlete. He has stated that his parents encouraged him to try new things and embrace challenges, which led him to pursue skeleton with full commitment.

Skeleton racing career

Montgomery began competing on the Skeleton World Cup tour in the 2006-07 season. He announced his arrival with a bronze medal in his very first World Cup race in Calgary in November 2006, finishing his rookie season ranked sixth overall with three additional top-ten finishes. His breakthrough came in the 2007-08 season, where he established himself as a world-class slider with five podium finishes. That season, he secured his first World Cup victory in Cesana, Italy, and earned four other podium results including silvers in Altenberg and Winterberg and a bronze in Königssee. His consistent performance led to a second-place overall ranking in the World Cup standings. At the 2008 FIBT World Championships in Altenberg, Germany, Montgomery won two silver medals, one in the men's skeleton event and another in the mixed bobsleigh-skeleton team event.

The pinnacle of his athletic career was the 2010 Winter Olympics in Vancouver and Whistler. Montgomery qualified for the Canadian team based on his results in the 2009-10 World Cup season, which included a victory in the World Cup event at Whistler that served as the Olympic test event. In the Olympic competition, he trailed Latvia's Martins Dukurs after the first run. He then posted the fastest times in the next two heats, setting a track record of 52.20 seconds on his third run. Entering the fourth and final run on February 19, 2010, he still trailed Dukurs by 0.18 seconds. Dukurs was 0.25 seconds slower on his final descent, and Montgomery's consistent performance secured the gold medal by a margin of 0.07 seconds. He became the second consecutive Canadian to win gold in the men's skeleton event, following Duff Gibson in 2006. After his win, Montgomery decided to build his own skeleton sled in an attempt to defend Canada's gold medal at the 2014 Games. He failed to qualify for the 2014 Winter Olympics in Sochi and subsequently announced he was 99 percent sure his skeleton career was over, marking his retirement from competition.

• 2006: World Cup debut. Wins bronze in Calgary.
• 2008: First World Cup victory in Cesana, Italy.
• 2008: Wins two silver medals at the World Championships.
• 2007-08: Finishes second overall in the Skeleton World Cup with five podiums.
• February 19, 2010: Wins Olympic gold medal in Vancouver.
• 2019: Inducted into the Manitoba Sports Hall of Fame.

The Olympic celebration and public connection

Immediately after his gold medal victory, Montgomery walked through Whistler Village where a stranger emerged from a pub and handed him a full pitcher of beer. Montgomery accepted it and drank from it as the surrounding crowd cheered and sang O Canada. This spontaneous moment was broadcast nationwide and quickly became a defining image of the Vancouver Games, symbolizing unscripted national pride and joy. Reflecting on the event years later, Montgomery stated that while the gold medal was the goal, the 'golden moment' with the beer was something that could not be planned. He explained that the moment resonated because while many may not see themselves on an Olympic podium, they could see themselves celebrating a personal achievement with friends. He has since said, 'If the beer is all I’m ever remembered for, I consider myself the luckiest fella on Earth.' The moment led to numerous media appearances, including on The Oprah Winfrey Show, and he later used his auctioneering skills to auction off singer Justin Bieber's cell phone number at the Juno Awards.

Montgomery also used his platform to promote causes he cared about. During his racing career, he wore an image of a painted turtle on his helmet, an endangered species in coastal British Columbia, to raise awareness for its conservation. In his post-Olympic interviews, he expressed hope that his performance would inspire more people to enter amateur sports and reassured parents that skeleton was a safe sport for children. He also voiced support for the establishment of an all-amateur sports channel dedicated to Canadian athletes.

Television hosting career

Montgomery's charismatic personality and comfort in front of cameras led to opportunities in television following his Olympic win. In the summer of 2010, he filmed the adventure sports television special Best Trip Ever for Discovery Channel Canada, which aired on November 27, 2010. He made a guest appearance as a judge on a Quickfire Challenge for the fifteenth episode of Top Chef: Texas in 2011. His major break came on June 5, 2013, when he was announced as the host of CTV's adaptation of the global franchise, The Amazing Race Canada. He has hosted all eleven seasons of the show since its inception, guiding teams across the country in a competition for a grand prize. His work on the series has been recognized with two Canadian Screen Awards for his hosting. In 2016, he further demonstrated his versatility by co-hosting the Juno Awards with singer Jann Arden. As of 2024, he remains the face of the popular reality competition.

Career as a motivational speaker and presenter

Beyond athletics and television, Montgomery has built a successful career as a professional motivational speaker. His speeches focus on themes of self-efficacy, teamwork, embracing challenges, and the power of belief in achieving personal and professional goals. Drawing from his own journey from a small-town prairie boy to an Olympic champion, he combines storytelling with humour and relatable anecdotes. Specific talk titles and themes include 'Dream Big and Believe It’s Possible,' which outlines the tools to build confidence, and 'The Power of Teamwork,' which discusses collaboration in families, workplaces, and communities. He also speaks on controlling one's attitude and the importance of moving forward, often stating, 'Whether you think you can, or you think you can’t... you’re 100% correct.'

Client testimonials frequently highlight his high energy, authenticity, and generosity with his time, including staying after events to take photos, show his gold medal, and engage with attendees. Feedback from events notes that his messages are referenced in conversations long after his presentations conclude. He has adapted his presentations for virtual formats, with clients noting his positive energy successfully translated to online audiences. Montgomery also participates in corporate and charity events, such as hosting a 'Guys’ Night Out' for Hudson’s Bay and auctioning a beer pitcher for 4-H youth at an agricultural conference.

Personal life and other ventures

Montgomery is married to Darla Montgomery, who is also a former skeleton athlete. The couple has two children: a son, Jaxon Mark, born on August 23, 2016, and a daughter, Lennon, born in 2019. He has a tattoo of a maple leaf with the word 'Canada' above it over his heart, which he got with his mother after his grade 12 high school graduation. When not hosting or speaking, he maintains his connection to the automotive industry, working as a sales consultant and automobile auctioneer in Calgary. His professional background also includes over 20 years of experience in leadership, learning and development, mentoring, and coaching, positioning him as an innovative consultant. Montgomery continues to be a proud advocate for Canadian pride and amateur sport, often emphasizing the importance of believing in one's dreams.

World Cup podium finishes and competitive record (2006 to 2010)

During his competitive skeleton career, Jon Montgomery achieved several podium finishes on the World Cup circuit, demonstrating his consistency at the highest level of the sport. His results show a rapid ascent from rookie to Olympic champion within four seasons. The following table highlights his key podium results leading up to and following his Olympic victory, illustrating the foundation of his success. His career overall ranking includes a sixth-place finish in his rookie 2006-07 season and the second-place finish in 2007-08, which stood as his highest World Cup placing.

These results, particularly his victory in the Olympic test event on the Whistler track, were strong indicators of his potential for success at the 2010 Games. His ability to perform on the biggest stage was the culmination of the experience and confidence gained from his World Cup achievements, including his first World Cup win in 2008 and a second overall World Cup finish in the 2007-08 season. Montgomery qualified for the 2010 Olympics based on his results in the 2009-10 Skeleton World Cup. He failed to qualify for the 2014 Winter Olympics and announced he was nearly certain his skeleton career was over. The lessons from his career, including resilience and innovation, are topics he now shares in his speaking engagements.

Philosophy and public messages

Central to Jon Montgomery's public persona is a philosophy centred on self-belief and proactive optimism. He frequently states that the greatest differentiator between achieving a goal and falling short is an individual's personal belief that they will succeed. He learned this lesson early in his skeleton career through a difficult experience that revealed his own self-doubt was the toughest hurdle to overcome. Montgomery advocates for living outside one's comfort zone and trying new things, as that is how he discovered his own passion for skeleton. He emphasizes that while we must be realistic about things we cannot change, we can always optimize our situations through creative thinking and innovation, noting that 'unless you’re moving forward, you’re getting left behind.'

His messages are delivered with a focus on relatability and Canadian pride. He encourages audiences to be proud of where they come from and to imbue themselves with the power of believing their dreams are possible. Montgomery frames his own story as that of a small-town boy who dreamed of representing Canada, not knowing which sport would be his vehicle, and highlights how keeping his eyes open to opportunities made his Olympic dream a reality. This narrative, combined with his humour and down-to-earth style, forms the core of his appeal as both a speaker and a public figure. His stated goal is to empower people with the confidence to accomplish what they seek, reminding them that they have the tools to work together, develop grit, and believe in themselves.

Questions about Jon Montgomery

How did Jon Montgomery get into skeleton racing?

Jon Montgomery discovered skeleton by chance in 2002 while visiting Canada Olympic Park in Calgary with his parents. He observed a skeleton race in progress and was immediately hooked on the sport. He soon enrolled in a Discover Skeleton school program to learn the basics. His natural aptitude and passion, coupled with his parents' encouragement to try new things, led him to quickly progress from novice to competitive athlete, making his World Cup debut just a few years later in 2006.

What is Jon Montgomery best known for?

Jon Montgomery is best known for two major achievements. First, he is celebrated for winning the gold medal in men's skeleton at the 2010 Vancouver Winter Olympics. Second, he is equally famous for the spontaneous celebration that followed, where he was handed a pitcher of beer by a fan in Whistler Village and drank from it as a crowd sang O Canada. This widely shared moment captured the nation's spirit. Since 2013, he has also become widely recognized as the host of The Amazing Race Canada.

What is Jon Montgomery's role on television?

Jon Montgomery is the host of CTV's The Amazing Race Canada. He was announced as the host on June 5, 2013, and as of September 2024, he has hosted all 11 seasons of the show. He also co-hosted the Junos in 2016 with Jann Arden. For his work on the show, he has earned two Canadian Screen Awards. This television role followed his earlier television appearances, including a special for Discovery Channel Canada in 2010 and a guest judge spot on Top Chef in 2011.

How did Jon Montgomery win his Olympic gold medal in 2010?

Jon Montgomery won the gold medal in men's skeleton at the 2010 Vancouver Olympics by a margin of 0.07 seconds. After the first run, he trailed Martins Dukurs. He then set the fastest times in the next two runs, including a track record of 52.20 seconds on his third run. In the final run on February 19, 2010, Dukurs was 0.25 seconds slower, allowing Montgomery to clinch the victory. He accepted his gold medal at the ceremony in Whistler on February 20, 2010, becoming the second consecutive Canadian to win the event after Duff Gibson in 2006.

What is the story behind Jon Montgomery's famous beer celebration?

After winning Olympic gold in 2010, Jon Montgomery spontaneously celebrated by walking through a crowd and drinking from a pitcher of beer handed to him by a fan. He later reflected that this 'golden moment' was unplanned, occurring as he passed a Whistler pub fresh from victory with his helmet under his arm. He stated that while people may not see themselves on an Olympic podium, they can connect with a moment of pride celebrated with a beverage. Montgomery has said, 'If the beer is all I’m ever remembered for, I consider myself the luckiest fella on Earth,' highlighting the moment's cultural resonance in Canada.

What are some details about Jon Montgomery's personal life?

Jon Montgomery is married to fellow skeleton athlete Darla Montgomery. They have two children: a son named Jaxon Mark Montgomery, born on August 23, 2016, and a daughter named Lennon, born in 2019. When not involved in skeleton or television, he works as a sales consultant and automobile auctioneer in Calgary. He is an alumnus of the Canadian Automotive Institute at Georgian College. Montgomery also has a tattoo of a maple leaf with the word 'Canada' above it, which he got with his mother after graduating high school.

Sources and further reading

• Jon Montgomery (Wikipedia)
• Jon Montgomery: Olympic Gold Medalist & Inspirational Speaker (jonmontgomery.ca)
• Jon Montgomery | Amazing Race Canada (speakers.ca)
• Jon Montgomery Speaking Engagements, Schedule, & Fee (wsb.com)
• Jon Montgomery, Team Canada (olympic.ca)

Checked by the Yadude Books desk. Last updated 2026-10-27.