Robert Douglas Flynn, Jr. is a former Major League Baseball infielder. Flynn was born and raised in Lexington, Kentucky. He attended Bryan Station High School, where he starred in baseball, basketball and football, playing quarterback on a 12-1 team. He went to the University of Kentucky on a combination baseball-basketball scholarship. While attending Kentucky, Flynn and some friends went to a Cincinnati Reds tryout camp. Flynn made the cut. After one more tryout camp and another audition at Riverfront Stadium, the Reds signed him as an amateur free agent in 1971.

He played for the “Big Red Machine” 1975 and 1976 World Series Champion Cincinnati Reds with Johnny Bench. Both Doug and Johnny are special attendees at our USA Cares Galas.

Doug also played with the New York Mets earning the 1980 National League Second Baseman Gold Glove Award. He also played with the Rangers, Expos and Tigers.

Flynn’s father, Bobby, was a second baseman in the Brooklyn Dodgers’ organization in 1948, and later played semi-pro ball with the Lexington Hustlers. While his son was coming up through the Reds’ minor league system, Bobby was also climbing politically, serving as Kentucky State Senator. His mother also played second base in fast-pitch softball for years. After retirement from baseball, Flynn spent a couple of years working in the Mets minor league system. He then headed up the State of Kentucky’s anti-drug program.

His wife of 32 years, Olga, is a former Philadelphia Eagles cheerleader whom he was set up with by Pete Rose. They were married in February 1982 and currently live in Lexington, Kentucky. Doug has been a banking officer for Central Bank, a locally owned, independent bank, since 1998.

In 1981, Flynn began singing country music songs at Cody’s, a club at Sixth Avenue and 16th Street in Manhattan on Monday, Tuesday and Wednesday nights.  When baseball went on strike in 1981, Flynn traveled a bit with the Oak Ridge Boys and sang on tour with them. He still loves to sing and pairs up with former Reds teammate Johnny Bench at their successful Children’s Charity Classic celebrity golf tournament held in Lexington, Kentucky every year on Cabaret Night.  Children’s Charity was founded in 1981 to help children’s charities in central Kentucky. Doug is a broadcaster on baseball games and still attends both New York Mets and Cincinnati Reds reunion events.

Doug is a patriot and supports many veteran causes.


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