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.
A Skating Wardrobe Malfunction That Could’ve Gone Bad
Ice dancers from Canada, Piper Gilles and Paul Poirier, hit a genuinely scary moment during their dance. During a lift-and-spin, an arm cuff from Poirier’s costume ripped off and snagged on Gilles’ tights while she was rotating on his shoulder. That’s the kind of thing that can turn into a brutal faceplant fast. Thankfully, Gilles reacted instantly, grabbed the loose fabric, and hid it behind her back like a real-life magician, without letting it touch the ice. That’s some real skills.
Medals Literally Breaking Apart
After multiple reports of Olympic medals breaking during celebrations on the opening weekend, the organizers promised to look into it. Downhill gold medalist Breezy Johnson warned people not to jump around too much because her shiny new trinket broke while she was celebrating. She later got a replacement, but similar mishaps reportedly hit at least two other athletes: Germany’s Justus Strelow and U.S. figure skater Alysa Liu. Alysa even posted a video of a ribbon-less medal. That’s all, thanks to the greedy execs trying to save as much money as possible.
The Olympic Village Ran Out of Condoms
Free contraception in the Villages has been provided for decades, but this year’s supply ran out faster than planned. An anonymous athlete reported that the stock ran out within roughly two to three days of the Olympics starting. First of all, kudos to the athletes and whoever else is allowed in the Olympic villages. Good on you all! But secondly, why didn’t the organizers order enough protection? Is this another case of greedy execs in action or just a logistical failure?
Lindsey Vonn’s Crash
Alpine skiing is thrilling because it’s beautiful and terrifying in equal amounts. Lindsey Vonn, repping for Team USA, had an unfortunate crash in a downhill run and was airlifted to a hospital, where she underwent surgery to stabilize a fracture in her left leg. Vonn later shared that her arm got hooked inside a gate, twisting her into the crash. She doesn’t seem to have any regrets and emphasized that racing is always a risk. Whether you love her or just respect the sport, it was a really awkward and painful moment to watch.
Snoop Dogg’s Security vs. a Speed Skating Legend
Snoop Dogg showed up in Milan as an honorary coach for Team USA, but the vibe got messy when Dutch commentator Marianne Timmer, a speed skating legend, said she was pushed up against a wall by Snoop’s security while trying to interview athletes. Timmer stated that she instructed Snoop’s goons to “act normal” due to the wide hallway and ample space, but the situation escalated further. This incident illustrates the clash between celebrity culture and true sports excellence.
Jake Paul Crying After Jutta Leerdam’s Win
Dutch speed skater Jutta Leerdam won gold in the women’s 1000m on February 9, reportedly setting an Olympic record time of 1:12.31. But the news outlets cared less about that and more about her fiancé, influencer/boxer Jake Paul, posting a video of him bawling his eyes out while celebrating with her family. A grown man crying tears of happiness should not be in the news, and yet here we are.
A Dog Crashed a Cross-Country Ski Race
And for dessert, we have a furry agent of chaos putting smiles on people’s faces. During the women’s cross-country team sprint in Lago di Tesero, a dog named Nazgul reportedly broke free and ran onto the course. Everyone loved it, officials did their best to tame the beast, and at least one athlete was so confused that she wondered if this was all a dream or a bad trip. Nazgul was quickly captured and returned home unharmed, and his owners reportedly said he’s the kind of dog who seeks people out and hates being left behind.
