Haley Winn's brothers - Ryan, Tommy, and Casey - showed up to support their sister yet again after their viral support for Winn during her gold medal performance at the 2026 Olympics.
The Winn Brothers, Ryan, Tommy, and Casey, arrived in style at Agganis Arena for the Boston Fleet’s 2-0 loss against the Toronto Sceptres.
The three went viral during the 2026 Milano Cortina Olympics for their support of their younger sister and Fleet defender Haley Winn. Ahead of the game, they were invited to drop the puck in a ceremony honoring the Olympians.
Ryan Winn spoke about the importance of showing up for his sister.
“We've been supporting our sister our whole life. It's not different for us. This isn't anything new; this isn't a show. This is authentically us. There's a lot more attention on it, more stuff comes up when there's attention on it, for sure. But this is what we've been doing since she first played hockey. We love doing it. We love supporting her; she's always been, like, a champion of the family.”
The three were suited up in USA tracksuits and eagle hats for the puck drop, but had several costume changes throughout the night. The brothers switched into sailor costumes at one point, showing off their Fleet pride.
“Yeah, it's always been this way, just us supporting her and everything she does. And we firmly believe that the attention they're getting, like they deserve this attention,” Ryan said. “They're amazing players, amazing people off the ice. The sport's growing, and they deserve it all.”
“We go back to, like, when she committed to Clarkson and she went to school for four years, there was no real place for her to play after college, like she was gonna go have fun at school, but she didn't know really if she was gonna be able to do it as a profession afterwards,” Tommy said. “So just to be able to do this for a living and in front of amazing fans, it's really cool to see for her.”
Haley had a team-high 11 minutes and 11 seconds on the ice on Tuesday and took one shot on net.
Following the loss, she spoke about the importance of her brother's support.
“Obviously it's awesome. I think they were a little surprised by everything that happened at the Olympics and stuff, but at the end of the day, it's just their support that obviously means everything. Having them my parents in the stands today. I mean, I can't ask for much more to have their support and getting more eyes on women's hockey,” Winn said. “I think they did a lot more than they thought, bringing a lot more fans to the game stuff. It was super cool to have them here today.”
The Winn brothers shared plans to attend the TD Garden game to continue to show up for their sister.
Haley, in the meantime, is gearing up for the Fleet’s next matchup on Saturday, when the team will take on the Seattle Kraken.