Thad Levine and Chet West sit down with Dan O’Dowd, Thad’s first boss and one of the most influential executives of his generation, for a behind-the-scenes look at building a Major League organization. Dan reflects on his path from Baltimore to Cleveland to becoming GM of the Colorado Rockies, the challenges of building a winner at altitude, the 2007 “Rocktober” run, and the realities of working with ownership. He also shares candid lessons from his career, including the decisions he would make differently today and the importance of finding the right balance between analytics, relationships, and leadership.

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