She was once Canada’s flag bearer at the Olympics.
Now, she’s hanging out with U.S. President Donald Trump, presenting him with gifts.
Among Canadian Olympic flagbearers, that goes down as a first.
Kaillie Humphries is still the most decorated bobsledder in Canadian Olympic history. She won gold for Canada in both the 2010 and 2014 Olympics, while bringing home bronze in 2018.
Kaillie Humphries won gold for Canada in 2010 and 2014 (Canadian Olympic Committee)
In the years since, however, she went through the process of becoming an American citizen. Humphries got engaged to an American and joined the U.S. bobsleigh team after a public split from Bobsleigh Canada Skeleton.
She now lives in California and has continued to win medals in bobsleigh. That included two bronze medal wins at the 2026 Olympics.
After picking up her fifth and sixth Olympic medals in Italy last month, the 40-year-old went public for her support of Trump.
“I’m a Republican,” Humphries said last month on Fox News, adding that she voted for Trump in 2024, her first election as an American citizen.
Voting for him is one thing, but presenting him with an award related to his support for Olympic athletes certainly shows another level of appreciation.
Humphries visited the White House on Thursday to present Trump with the Order of Ikkos, which is an award “presented by Team USA medal-winning athletes to a coach, mentor or other individual who has been instrumental in their success.”
@nypostOlympic bobsled champion Kaillie Humphries surprised President Trump Thursday by awarding him the Order of Ikkos medal during a Women’s History Month event at the White House.♬ original sound – New York Post | News
Typically, it is a fellow coach or athlete who gets the medal. But Trump is the first American president to receive the award since it was created back in 2008.
“I want to support and recognize the impact you’ve had on women’s sports throughout the Olympic movement,” Humphries said.
“Specifically, standing up to keep biological women in women’s sports.”
Last February, Trump signed an executive order commonly known as “Keeping Men out of Women’s Sports,” while vowing to get rid of “transgender insanity” in U.S. schools.
“I knew I liked her,” a grinning Trump replied as he accepted the award.
There’s obviously unintended irony in Trump receiving an award in support of Olympic athletes.
The 79-year-old called U.S. skier Hunter Hess “a real loser,” after the Oregon native said he had “mixed emotions” about competing for the United States. In previous years. Trump also clashed with Olympians Megan Rapinoe and Gwen Berry.
His comments about the women’s hockey team also made international headlines. While Hilary Knight, captain of the U.S. team, called it a “distasteful joke,” Humphries downplayed it.
“I personally don’t believe that his intention was meant for the way it came across,” she said when asked about it on Fox News.
“It’s sad that you are going to diminish an accomplishment, a great accomplishment, knowing they haven’t won in 46 years,” she said.
“For any athlete to get invited to the White House and to be proud to represent your country… whether they voted for him or not, you get to celebrate with the ultimate person that runs our government, I would have gone if I got invited.”
Well, despite not receiving an invite, it looks like Humphries found a way to the White House after all.