10 Best, Worst, WTF Moments From the Winter Olympics

While the 2026 Milan Cortina Olympics has showcased some of the greatest athletes in the world and extraordinary displays of sportsmanship, they’ve also been some of the messiest Games in recent memory. Rumors about penis injections were swirling, condoms were running out, and a fugitive hockey fan was arrested after 16 years on the run. We’re talking Bravo levels of drama.

In case you haven’t spent the past two weeks glued to Olympic coverage, here are 10 of the most memorable moments of the 2026 Milan Cortina Games.

Best: Slovenian Skier Siblings Make History

Domen and Nika Prevc, brother and sister ski jumpers from Slovenia, arrived in Milan as gold medal favorites. The siblings lived up to the hype, with Nika taking silver in the women’s normal hill event, and Domen winning gold in the men’s large hill event. On top of that, the pair — along with their teammates, Anže Lanišek and Nika Vodan — won the gold medal in mixed team ski jumping. This made Domen and Nika the first brother and sister to win a medal on the normal hill at the same Olympics.

But that’s not all the Prevc family has accomplished. Domen and Nika have two older brothers, Cene and Peter, who both medaled in (what else) ski jumping at the 2022 Beijing Games. Thanks to Domen and Nika’s success in Milan, the Prevc family is the first to have four siblings each earn a Winter Olympic medal.

Worst: Olympic Village Ran Out of Condoms After 3 Days

Since 1988, horny athletes have enjoyed a seemingly unlimited supply of free condoms available in the Olympic village. But there must be something in the air in Milan, because this year’s 2,800 Olympians blew through roughly 10,000 condoms in three days, Italian outlet La Stampa reported.

The International Olympic Committee (IOC) confirmed the condom shortage, blaming “higher-than-aniticipated” demand, and said that they planned to “continuously replenish until the end of the Games to ensure continued availability.” The Olympic village’s condoms were, in fact, restocked.

WTF: Biathlete Sturla Holm Lægreid Begs Girlfriend for Forgiveness After Cheating on Her

In a post-race interview shortly after winning a bronze medal, Norwegian biathlete Sturla Holm Lægreid said that he had a message for someone “who might not be watching today”: his ex-girlfriend. He explained that they dated for six months, but that three months ago he cheated on “the love of [his] life, the most beautiful and kindest person.”

Lægreid opted to tell his girlfriend about his infidelity one week before he competed in the Olympic Games. “It’s been the worst week of my life,” he told Norwegian Broadcasting Corp. But he didn’t stop there.

“I’m not ready to give up,” Lægreid said. “I hope that committing social suicide [like this] might show her how much I love her. I accept the consequences of what I’ve done. I regret it with all my heart. Maybe I’m dumb as a rock. I’m a member of Mensa, but I still do stupid stuff.”

A few days after his stunt, Lægreid’s ex-girlfriend, who understandably wishes to remain anonymous, told Norwegian tabloid VG that it will be “hard to forgive” him for cheating on her and airing their dirty laundry on the world stage.

“I did not choose to be put in this position, and it hurts to have to be in it,” she told the publication. “We have had contact, and he is aware of my opinions on this.”

Worst: A Ukrainian Athlete’s Memorial Helmet Got Him Disqualified

A Ukrainian skeleton racer was disqualified from the Winter Olympics after insisting on wearing a “helmet of remembrance” featuring images of 24 Ukrainian athletes and coaches killed in the war with Russia. He was “not allowed to participate at Milano Cortina 2026 after refusing to adhere to the IOC athlete expression guidelines,” the IOC said in a statement, referring to rules prohibiting any kind of political statement by competitors.

The IOC did, however, offer to display his helmet during all training runs and immediately after the skeleton competition. But Vladyslav Heraskevych refused to back down and compete without his helmet because, he said, there are things that are “more important than medals.”

Best: Flavor Flav Goes From Hype Man to Olympic Hopeful

The USA Bobsled and Skeleton team rolled up to the 2026 Olympics with a secret weapon: Flavor Flav. In October the team announced that the Grammy-nominated Olympics superfan would serve as their official hype man and sponsor. “The partnership is a blessing,” Flav said in a statement. “It’s cooler than Cool Runnings. It’s Coolest Runnings.” But he wanted more.

After cheering on the team — especially the women — from the sidelines in Cortina, Flav decided that he wanted to get in on the action. “Yes, your boy has taken a ride in the 4 man bobsled, but im an adrenaline junkie and needed to try skeleton,” he wrote on X on Monday. “And now I’ve officially joined the team and am gonna try to start competing. 66 yo going 66 mph.”

On Thursday, Flav discussed his desire to compete for the U.S. Bobsled and Skeleton team in a video with its coaches. “You’d better watch out because you know what, you might find me in the Olympics next year,” Flav says in an Instagram video from USA Bobsled and Skeleton. “I’m going to train skeleton and bobsled. That’s right: I’m with my future coaches, boyeeeeeeee.”

WTF: ‘Penisgate’ Put the Spotlight on Male Ski Jumpers’ Crotches

The World Anti-Doping Association (WADA) is investigating claims that male ski jumpers inject their penises with hyaluronic acid in a scandal dubbed “Penisgate” by the German outlet Bild.

So what do schlong shots have to do with ski jumping? Believe it or not, there’s a scientific explanation. The hyaluronic acid plumps up the penis, so that when 3D scanners measure them for their ski suits, they should, at least in theory, be issued a larger, looser suit. This, in turn, could help them jump longer distances, with the suit’s baggy crotch acting like a sail catching wind.

The concept isn’t as far-fetched as it sounds: a study published in the journal Frontiers found that a 2 cm change in the size of a ski jumping suit could mean gaining an extra 5.8 meters in jump length.

For now, no ski jumpers have been caught doing this at the Olympics. However, one plastic surgeon has confirmed that he injected a “generous dose of hyaluronic acid” into the penis of a ski jumper last month, though he wouldn’t disclose the athlete’s nationality or whether he was competing in the Olympics.

Best: The ‘Minions’-Themed Skating Routine Made It to the Ice

All Spanish figure skater Tomas-Llorenc Guarino Sabate wanted to do was perform his Minion routine at the Olympics. He had been entertaining crowds with the program — featuring four cuts of music from the Minions movie, and him dressed as a Minion — all season, and thought he had approval for his songs and costume. Turns out, he didn’t, and found out four days before the Olympics’ opening ceremony.

But Sabate didn’t let this derail his Olympic dreams. Instead, he dusted off a Bee Gees routine from last year, stayin’ alive in the competition and making the best out of a bad situation. It all worked out in the end, though — Sabate’s Minion music was approved two hours before the Olympic figure skating program opened with the team event.

Worst: The ‘Quad God’ Doesn’t Make the Podium

American figure skater Ilia Malinin — nicknamed the “Quad God” — arrived at the Olympics as the overwhelming favorite to win gold in the men’s competition. While he came out of the short program with a 5.09-point lead, he fell multiple times during free skate, and came in eighth overall. Not only that, but he failed to land any of the quadruple jumps that he’s known for, leading to one of the most shocking upsets in U.S. figure skating history.

Fortunately for Malinin, he’ll also be remembered for landing the first legal backflip on Olympic ice since 1976. The controversial move was banned that year after American Terry Kubicka did one at the 1976 Innsbruck Games. But the most famous backflip of all time came courtesy of France’s figure skating powerhouse Surya Bonaly at the 1998 Nagano Olympics. When it became clear that Bonaly wasn’t going to medal, she included an illegal backflip in her final program, landing on one skate. The International Skating Union lifted the backflip ban in 2024 — though it still doesn’t add points.

WTF: A Slovak Hockey Fan on the Run for 16 Years Is Arrested

On Feb. 11, Italian police arrested a 44-year-old Slovak fugitive who had been on the lam for 16 years. The warrant for his arrest was issued in 2010 after he committed a string of thefts in Italy. Despite being wanted in the country, the man returned to Italy to cheer on the Slovak hockey team at the Olympics.

But his love for the game ended up being his downfall. Local police found the hockey fan at a guesthouse on the outskirts of Milan, and promptly took him to prison, where he’ll serve 11 months and seven days for his crimes.

Worst: Trump Calls U.S. Olympian ‘A Real Loser’

At a news conference on the first day of the Games, when asked what it means to represent the United States in the current climate domestically and internationally, U.S. freeskier Hunter Hess said it “brings up mixed emotions” and was “a little hard.” He continued: “There’s obviously a lot going on that I’m not the biggest fan of and think a lot of people aren’t… But just because I’m wearing the flag doesn’t mean that I represent everything that’s going on in the U.S.” Hess went on to clarify that he was proud to represent his “friends and family back home, and all the things that I believe are good about the United States.”

Naturally, President Donald Trump couldn’t resist weighing in, writing on his Truth Social platform: “U.S. Olympic Skier, Hunter Hess, a real Loser, says he doesn’t represent his Country in the current Winter Olympics. If that’s the case, he shouldn’t have tried out for the Team, and it’s too bad he’s on it. Very hard to root for someone like this.”