From Pro Bowls to the Top 100: Drew Bledsoe on Building Excellence — Twice

Drew Bledsoe knows what it means to reach the top — early. The youngest quarterback ever named to a Pro Bowl, Drew later saw his very first wine vintage earn a spot on Wine Spectator’s Top 100.In this episode of Crosby’s Cru, Drew shares how excellence, loyalty, and long-standing relationships have shaped both his football career and his winery. From honoring the franchises he played for to giving real ownership and recognition to his winemaker, this conversation goes beyond accolades to explore what it means to build something the right way — where everyone involved rises together.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What this episode covers

Drew Bledsoe knows what it means to reach the top — early. The youngest quarterback ever named to a Pro Bowl, Drew later saw his very first wine vintage earn a spot on Wine Spectator’s Top 100.In this episode of Crosby’s Cru, Drew shares how excellence, loyalty, and long-standing relationships have shaped both his football career and his winery. From honoring the franchises he played for to giving real ownership and recognition to his winemaker, this conversation goes beyond accolades to explore what it means to build something the right way — where everyone involved rises together. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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This episode is 1 hour and 20 minutes long.

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This episode was published on December 31, 2025.

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