Welcome to another episode of Inside The Game with Pierre McGuire. In this conversation, Pierre sits down with Matt Keator, founder of WIN Hockey Agency, for a rare look inside the business side of hockey and what it takes to represent players at the highest level.

Keator reflects on how he got his start as an NHL scout, the mentors who helped shape his view of the game, and why relationships, trust, hockey sense, and communication have been central to his career as an agent. From Ronnie Caron and Ted Hampson to John Dunham and Ian Moran, Keator shares the lessons that shaped the way he evaluates players and builds long-term careers.

The conversation dives into the modern NHL through the lens of player representation, including Adam Fox's path to the New York Rangers, Chris Kreider's move to Montreal, Leo Carlsson's major contract, and why today's league has become more player-driven than ever before.

Pierre and Matt also discuss Zdeno Chara's influence, what elite habits really look like, the importance of culture in winning organizations, NHL expansion, Canadian markets, the Olympics, labor harmony, and the future growth of the sport.

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Produced by 1TEAM Media.