Doug Flynn Behind the Stories

Doug Flynn Behind the Stories

June 25, 2026 · 59 min · Season 2 · Episode 23

About this episode

Doug Flynn shares his journey from a multi-sport athlete in Kentucky to a two-time World Series champion and Gold Glove winner in Major League Baseball.

In this episode, we sit down with former Major League infielder Doug Flynn, a two-time World Series champion, Gold Glove winner and one of the most respected defensive players of his era. Doug takes us on a journey from his days growing up in Kentucky, where he starred in football, basketball, and baseball, to earning a dual scholarship at the University of Kentucky and playing for legendary coach Adolph Rupp. What started as a trip to an open Cincinnati Reds tryout with friends turned into an unlikely path to professional baseball and eventually a spot on one of the greatest teams in baseball history, the famed Big Red Machine. We discuss Doug's rapid rise through the minor leagues, making his Major League debut with the Reds, winning back-to-back World Series championships in 1975 and 1976 alongside Pete Rose, Joe Morgan, Johnny Bench, and Tony Pérez, and his memorable first big-league hit against the Dodgers. Doug shares his perspective on the blockbuster 1977 trade known as the "Midnight Massacre" that sent him to the New York Mets in exchange for Tom Seaver. We also dive into his 1980 Gold Glove season, the historic game in Montreal where he became the first and only Met to…

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