10 Most Awkward Moments of the 2026 Winter Olympics

The Olympics are primarily about showcasing athletic greatness, but during the nearly three-week spectacle, there’s always room for unforeseen events that the media eagerly focuses on. This time around, we got headlines about judging drama, disqualifications, food complaints, wholesome surprises, and at least one dog who clearly wanted their moment on NBC.

Here are the strangest, most awkward, and most talked-about moments of the 2026 Winter Olympics.

A Slovak Fan Got Arrested After 16 Years on the Run

In a plot twist that sounds like it came from a ’90s C-tier crime comedy, a 44-year-old Slovak hockey fan was arrested while trying to attend the Slovakia vs. Finland match. Imagine being wanted for stealing stuff, fleeing the country for 16 years, then coming back to see your national team compete (probably thinking everyone moved on), and getting caught by the police. That’s pretty much how the story goes for our low-IQ shoplifter, who was identified after checking into a guesthouse outside Milan, got detained, and missed the game. Not just any game, but one where Slovakia beat Finland 4–1!

JD Vance Got Booed at the Opening Ceremony

The opening ceremony at San Siro had star performances, dramatic staging, and the parade of nations. Team USA got cheers as they entered, led by speed skater Erin Jackson. Then the big screen showed U.S. Vice President JD Vance and Second Lady Usha Vance, and the crowd flipped from “WOO!” to “BOO!” really dang fast. The awkwardness wasn’t subtle, especially with commentators reacting and cringing in real time.

Vladyslav Heraskevych Disqualified Over a “Helmet of Remembrance”

This one wasn’t quirky or funny. It was pretty heavy and controversial. Ukrainian skeleton racer Vladyslav Heraskevych was disqualified on February 12 over a helmet design honoring Ukrainian athletes who died in combat after Russia’s invasion. IOC President Kirsty Coventry said she met with Vlad before the event, hoping to convince the athlete not to wear the helmet or wrap it in a cloth, arguing that the contestants can’t include messaging under IOC rules. Heraskevych responded that the decision echoed Russia’s narrative and disrespected the memory of those lost. It was a stark reminder that you cannot separate the Olympics from international politics.