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Milan Today
By the People, for the People
U.S. Women's Hockey Star's Eccentric Brothers Steal the Spotlight
Haley Winn's three brothers go viral for their over-the-top outfits and reactions at the Olympics
Published on Feb. 23, 2026
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When Haley Winn, a 22-year-old defender for the U.S. women's hockey team, made the Olympic roster, her three brothers Tommy, Casey, and Ryan immediately began planning their outrageous outfits and antics to support her. Wearing matching American flag tracksuits, bald eagle masks, and more, the brothers gained viral fame on social media and even made an appearance on the "Today" show for their enthusiastic cheering and reaction videos to Haley's goals.
Why it matters
The Winn brothers' exuberant support for their sister Haley, an Olympic hockey player, has captured the hearts of fans and highlighted the special bond between athletes and their families at the Games. Their over-the-top outfits and celebratory videos have gone viral, showcasing the lengths that devoted family members will go to cheer on their loved ones competing on the world stage.
The details
When Haley Winn, 22, made the U.S. women's hockey team for the 2026 Olympics in Milan, her three brothers Tommy, Casey, and Ryan immediately began planning their outfits and antics to support her. Their packing lists included American flag tracksuits, matching bucket hats, stars-and-stripes socks, bald eagle masks, cowboy boots, and newsboy caps. The brothers' reaction video to Haley's first Olympic goal, which showed Tommy spilling his beer from excitement, drew hundreds of thousands of views online.
- In January, after it was announced that their sister Haley had made the Team USA roster, the brothers began brainstorming their outfits.
- By February, the brothers had their Milan Cortina packing lists finalized with their eccentric attire.
- On February 23, 2026, the brothers' reaction video to Haley's first Olympic goal went viral online.
The players
Haley Winn
A 22-year-old defender for the U.S. women's hockey team who competed in the 2026 Olympics in Milan.
Tommy Winn
One of Haley Winn's three brothers who gained viral fame for his eccentric outfits and enthusiastic reactions supporting his sister at the Olympics.
Casey Winn
One of Haley Winn's three brothers who gained viral fame for his eccentric outfits and enthusiastic reactions supporting his sister at the Olympics.
Ryan Winn
One of Haley Winn's three brothers who gained viral fame for his eccentric outfits and enthusiastic reactions supporting his sister at the Olympics.
What they’re saying
“I thought maybe we'll just get some Jumbotron time and all of a sudden we're on the 'Today' show.”
— Tommy Winn (The New York Times)
What’s next
The Winn brothers plan to continue their over-the-top support for Haley throughout the remainder of the Olympics in Milan.
The takeaway
The Winn brothers' enthusiastic and eccentric support for their sister Haley, an Olympic hockey player, has captured the hearts of fans worldwide and highlighted the special bond between athletes and their families at the Games. Their viral antics have shown the lengths that devoted family members will go to cheer on their loved ones competing on the world stage.
