how old are the winn brothers

February 21, 2026

The Winn brothers—Casey, Ryan, and Tommy—are the older siblings of U.S. Olympic hockey player Haley Winn, who've recently gone viral for their colorful, matching outfits and enthusiastic support at the 2026 Winter Olympics in Milan-Cortina.

Ages and Background

Casey Winn is currently 29 years old , making him the eldest of the trio who all grew up playing hockey in Williamson and Webster, New York.

Ryan Winn, the middle brother, attended Bowdoin College from 2017 to 2021 (suggesting a birth year around 1998-1999, placing him roughly 26-27 now) and works as a marketing executive with his own production company.

Tommy Winn rounds out the group; while his exact age isn't specified in recent coverage, he's part of the same college hockey-playing crew as his brothers, likely in his mid-to-late 20s.

Why They're Trending

These brothers have turned heads beyond the rink, dressing in coordinated, over-the-top costumes for every U.S. women's hockey game to hype their sister Haley (age 22).

Their TikTok videos, started at the 2022 Worlds and amped up for the Olympics, capture wild reactions and celeb encounters—like chatting with Abby Wambach and Snoop Dogg—shifting some spotlight to sibling love amid Haley's standout play (one goal, three assists so far).

Ryan told the Today show it began as a fun family tradition: "We did an outfit together, then we kinda built it from there," emphasizing unity and keeping eyes on women's hockey.

Family Hockey Legacy

All three brothers were college defensemen: Casey at SUNY Brockport, Ryan at Bowdoin, and Tommy at SUNY Geneseo.

Haley, dubbed "the absolute beast out of all of us" by Ryan, outshone them despite starting young—skating before she could walk on the family backyard rink.

Now with the Boston Fleet in the PWHL (drafted second overall last year), Haley's Olympic debut has the whole crew crashing hotels and cheering loud, embodying tight-knit support.

Brother| Age (2026)| College Hockey| Fun Fact [web:#]
---|---|---|---
Casey| 29| SUNY Brockport| Eldest, shared Haley skated with a bucket as a tot 71
Ryan| ~26-27| Bowdoin (2017-21)| TikTok star, founded Winning Productions USA 3
Tommy| Mid-20s| SUNY Geneseo| Part of the viral outfit squad 1

TL;DR at Bottom: Casey (29), Ryan (~26-27), Tommy (mid-20s)—fierce hockey bros stealing the 2026 Olympics show for sister Haley.

Information gathered from public forums or data available on the internet and portrayed here.