Winners Club

The Winn Bros

You may have come across us because of our 2026 Milan Olympic antics. We will always bring the hype but winning looks different from the inside. Winners Club is a culture-first podcast from the WinnBros — three brothers obsessed with sports, stories, and the moments that shape success. From Olympic runs to everyday grinders, we break down what winning really takes — the mindset, the chaos, the people behind the scenes, and the culture that fuels it all. Less hot takes. More real perspective.

Episodes

  1. May 8

    Does The PWHL Have a Hitting Problem | Winners Club Ep.4

    On Episode 4 of Winners Club, the boys dive deep into the intensity and controversy surrounding the Professional Women's Hockey League playoffs, especially the conversation around physicality, inconsistency in officiating, and where the line should actually be drawn with hitting in women’s hockey. Does the league need to fully commit to a more physical identity or tighten things up for consistency? The episode also follows Ryan’s journey covering the Tampa Bay Lightning playoff run alongside Coach Chippy and Always Hockey, giving a behind-the-scenes perspective on being around the organization, the fanbase, and the energy surrounding playoff hockey in Tampa. Ryan talks about how those experiences shaped his connection to the Lightning and why he’s become such a big Tampa fan — from the culture around the team to the way the city rallies behind playoff hockey. The boys also touch on the emotional highs and frustrations of playoff sports as a whole, bouncing between NHL and PWHL storylines while keeping the episode centered on hockey culture, fan identity, and the chaos that makes playoff season so addicting.

  2. May 1

    Pressure Makes Moments | Winners Club Ep. 3

    Playoff spots, championship runs, and absolute chaos across the sports world. The PWHL heats up as the Boston Fleet clinch a playoff spot and the MVP race tightens. In college hockey, Wisconsin Badgers women's ice hockey go back-to-back, Lacey Eden secures her fourth national title, and Tessa drops the puck in the championship after a tough semifinal loss—full circle moment. Meanwhile, KK Harvey stacks one of the wildest single-year résumés ever. On the men’s side, Hamilton Continentals take down Hobart Statesmen in OT, and the Frozen Four is loaded. March Madness brings the drama as Duke Blue Devils men's basketball collapse against UConn Huskies men's basketball. The NHL turns chaotic—Vegas fires Bruce Cassidy late and brings in John Tortorella, while Leon Draisaitl is out until playoffs. We also hit Tiger Woods, a wild FDNY vs NYPD game ending in a brawl after NYPD snaps a 16-year losing streak, and Major League Baseball Opening Day with the new ABS strike zone.

  3. Mar 30

    What They Don’t Show You at the Olympics feat. Haley Winn | Winners Club Ep. 2

    On this episode the Bros are joined by their superstar sister while they are in Boston for a ceremonial puck drop. They break down St. Patrick's Day in Boston, their upcoming plans / outfits, as well as ongoing events in the world of sports. Haley gives behind the scenes insight on her time at the olympics and what she thought of all the off the ice shenanigans. She also has a laughing attack... a bad one.

  4. Mar 11

    Milano Cortina 2026 — What the World Didn’t See | Winners Club Ep. 01

    In our first episode, the WinnBros share their perspective on the 2026 Olympics — the moments, the energy, and everything we experienced as fans and brothers. We’re incredibly grateful for the love and support around our off-ice antics, and we want you involved in shaping the conversations on this show. A big part of our journey is supporting our sister Haley, but Winners Club goes deeper — exploring success, the unseen work behind it, and the people and support systems that make great moments possible.

  • 4 Episodes

Ratings & Reviews

5
out of 5
2 Ratings

About

You may have come across us because of our 2026 Milan Olympic antics. We will always bring the hype but winning looks different from the inside. Winners Club is a culture-first podcast from the WinnBros — three brothers obsessed with sports, stories, and the moments that shape success. From Olympic runs to everyday grinders, we break down what winning really takes — the mindset, the chaos, the people behind the scenes, and the culture that fuels it all. Less hot takes. More real perspective.

Information

  • Creator
    The Winn Bros
  • Years Active
    2026
  • Episodes
    4
  • Rating
    Explicit
  • Copyright
    © 2026 The Winn Bros
  • Show Website
    Winners Club