When the Winn brothers began planning their matching outfits for the Olympics, Tommy thought that he, Casey and Ryan might get featured on the Jumbotron for their antics.
They met that goal, while wearing plastic bald eagle masks they could barely breathe in or see through. And on social media, they were noticed by millions.
“I thought maybe we’ll just get some Jumbotron time and all of a sudden we’re on the ‘Today’ show,” Tommy Winn, 25, said on Saturday, adding, “It was pretty crazy.”
In January, after it was announced that their sister, Haley Winn, 22, had made the Team USA roster for women’s hockey, the brothers began to brainstorm.
By February, their Milan Cortina packing lists included American flag tracksuits with matching bucket hats, stars-and-stripes socks, the bald eagle masks, cowboy boots and newsboy caps.
Their fervent reaction video to their sister’s first Olympic goal — scored six minutes into what would become a 5-0 win over Switzerland in the preliminary round and made Tommy Winn so excited that he spilled his beer — drew hundreds of thousands of views.
The comment sections of TikTok and Instagram loved them. Walmart commented, “the matching outfits are tea,” referring to their tracksuits and bucket hats.
The fact that the Winn brothers were the only spectators wearing jorts at the Americans’ 6-0 victory over Italy in the quarterfinals also caught attention. As did their accompanying hype video, which featured the three men doing push-ups in the streets of Milan set to “Eye of the Tiger.”
“None of us planned on this happening,” said Ryan Winn, 27, who works as a video producer in Nashville, Tenn., and can be credited for the high production value of the social media posts.
“None of us knew that it was possible for it to catch this much fire,” he said.
The idea had been to make some funny videos to drive attention to their sister, whom they described as relentlessly hard-working (her skills coach used to have to tell her to go home) and exceedingly humble.
In an elementary school yearbook, Winn, now a defender for the Boston Fleet and who was drafted by the team second overall in the 2025 Professional Women’s Hockey League draft, had listed her life goal as “hockey Olympian” under her picture, Tommy Winn recalled.
She accomplished that by age 22 and walked away with a gold medal on Feb. 19.
Their father built the Winn siblings a backyard ice rink in the winters in Rochester, N.Y. The four of them would play hockey for hours.
Haley Winn, the youngest, was on the ice before she was even 2, leaning on and pushing an overturned bucket to stabilize herself enough to skate.
But as much as her three brothers adored her, “we weren’t easy on her,” Ryan Winn said.
They would not hesitate to give her a cross check or push her into a snowbank.
She played on boys teams before she was 13, Casey Winn, 29, said, even when the players could hit. That’s when he realized how good his sister was.
When she started dominating in high school games, it dawned on him that “she’s one of the best defensemen in the world at her age level.”
“If she’s not going to be loud about it,” Ryan Winn said, “we’re going to be really loud.”
He said that their Olympic gimmicks were not just about promoting their sister. The brothers wanted people to pay attention to the “extremely talented” U.S. women’s hockey team.
In Milan, the creativity began flowing and the brothers started waking up early to film.
Other siblings got involved, like forward Abbey Murphy’s brothers, Patrick and Dominic, and defender Caroline Harvey’s brother, Nolan. Some player’s parents filmed with them.
Celebrities came, too. The Winns met Snoop Dogg. They were stunned when Abby Wambach, a soccer legend they’ve admired since they were young, asked to take a picture with them.
Despite the whirlwind of fun, their tone shifted on Thursday when the Americans reached the gold medal game against Canada, in a contest known as one of the most heated rivalries in sports.
In a video on TikTok, they sported the simple look of matching USA hockey jerseys with “Winn” and their sister’s No. 8 on the back.
“Because it’s not about us,” Ryan Winn said in a voice-over on the video. “It’s about the women on the ice. It’s about the legends who have paved the way. It’s about those who are changing the game.”
That sentiment is what is resonating with fans, they suspect.
With the Professional Women’s Hockey League in its third season, and expansion teams recently added in Seattle and Vancouver for the 2025-26 season, fandom of women’s hockey is growing.
The game on Thursday was the most-watched women’s hockey game on record in the United States, according to NBC Sports, with an average of 5.3 million viewers across USA Network and Peacock. In overtime, the game’s audience reached 7.7 million viewers.
Based on the support for the Winn brothers, fans also love to see over-the-top recognition of the players.
At Thursday’s gold medal game, Casey Winn couldn’t sit to watch the warm-ups as he usually would. He had a pit in his stomach but still managed to get some drinks down, to settle his nerves.
Ryan Winn felt tingly. Tommy Winn clocked in when the U.S. team took a penalty with five minutes left in the game while down 1-0.
At three minutes, he thought, “The girls got to do something right now.”
And they did.
With two minutes left in regulation, Hilary Knight, the team captain at her fifth Olympics, scored a tying goal. It was history. Her 15th Olympic goal, the most career goals scored in U.S. women’s Olympic hockey history, tied the game at 1, forcing overtime.
Four minutes into overtime, Megan Keller, one of Winn’s teammates on the Boston Fleet, took a long stretch pass, and beat both a Canadian defender and the goalie to clinch the gold.
As for the brothers?
They watched a game where their sister was consistent and reliable. She cleared pucks to the net, blocked shots and took some shots of her own.
As she exited the ice wrapped in an American flag and rushed to her brothers in the stands, all four siblings were crying.
“You’re the best in the world,” they told her, again and again.
“I will never watch another sports game and feel what we felt in the game-tying goal, in the overtime winner,” Ryan Winn said. “Ever.”
The brothers all agreed.
“This really became our dream,” Casey Winn said, “to cheer on her dream.”
Lauren McCarthy is a reporter on The Times’s Investigations team who also covers breaking news and other topics.
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