In this episode of Long Story Short, we sit down with Michael Copeland, President and CEO of Woodbine Entertainment, whose career has spanned law, consulting, and professional sports leadership. Michael opens up about what it takes to navigate bold career pivots from corporate law to leading one of Canada’s most iconic sports organizations, and the lessons learned along the way. We talk about what’s unfolding at Woodbine, how the company is transforming its role in Canadian sports and entertainment, and what it means to lead through both innovation and public scrutiny. Michael also reflects on his time at the helm of the CFL, what it’s like to “catch the heat” from passionate fans, and how resilience, curiosity, and a willingness to reinvent yourself can redefine success.