Sydney Hill

Doug Flynn is a retired professional baseball player from Lexington, Ky. His parents instilled the love of baseball in him from a very young age. His father played with the Brooklyn Dodgers for one year in the minor leagues, and his mother was on a fastpitch softball team. Still, Flynn’s professional baseball story isn’t a regular one. He didn’t get drafted or recruited to the major leagues, and he didn’t expect to become a professional ballplayer.

Flynn was born and raised in Lexington. He played Little League with the Lexington Colts and went on to play with an all-star team after he turned 13 years old. Flynn enjoyed growing up in the Lexington community. He said back when he was younger, he used to be able to drive around Lexington and stop and wave or talk to almost anyone.

Flynn wasn’t just a baseball player. He also played football and basketball at Bryan Station High School. Flynn never won any All-Cities, All-States, or any other big awards in high school; he said that he was a decent player, but he wasn’t “the player.” Still, he made it all the way to the major leagues.

Flynn wasn’t originally offered any scholarships coming out of high school. However, one day he received a phone call from the then-head basketball coach at the University of Kentucky, Joe B. Hall, asking if Flynn would be interested in playing basketball for him. After realizing that the offer wasn’t a joke, he accepted, playing point guard for his entire freshman year of college despite being only 5’8.

Flynn also played UK baseball his freshman year. 

“I didn’t get to play baseball very much,” he said. “There were a lot of guys who were better than me.” 

After his freshman year at UK, he took an opportunity to go down to a junior college to mature and become a better player. Shortly afterward, his friends woke him up one morning to go try out for the Cincinnati Reds. Flynn went through a long tryout process, after which a scout named Chet Montgomery offered him an opportunity to come and play for the Reds. 

Flynn played professional baseball for 11 years. He was a member of two world championship teams with the Cincinnati Reds, and he won a Golden Glove award while playing with the New York Mets.

After his baseball career ended, Flynn returned home to Lexington and played professional softball all over the country for seven years. Flynn has always felt connected to his hometown, and he loves to come back and celebrate his accomplishments with his friends and family.

“I have always felt like if you have any kind of position or title or recognition that you can have an impact or an influence on giving back,” Flynn said. He volunteered at the Cincinnati Reds Fantasy Camps for several years and volunteered for nine years with a program called Champions Against Drugs. He is still involved with the Children’s Charity Golf Classic, Hope for the Warriors, and USA Cares. 

Though Flynn never served in the military, he said he volunteers for military causes because “people made sacrifices in order for us to go out and fulfill our dreams of becoming professional ballplayers.”

“The least we can do is give back,” he said.

Flynn is also an on-air broadcaster for the UK baseball team. He brings his professional experience and his love for the game to the ballpark, and he shares it with players and viewers at home. He doesn’t remember how many years he has been doing it, but he loves having the opportunity to be involved at UK.

“Why did I make it and somebody else didn’t? I just think that God blessed me in putting me in a position that I could do the things that I enjoy doing. He already knows the desires of your heart, and he knows I liked to play ball, and I got to play,” Flynn said. “I don’t take credit for any of it. I am just thankful that it happened.”