Jimmy Key began his athletic career in the Little Leagues while attending McDonnell Elementary School and Stone Middle School. While pitching for the 12 year old All-Star team, Jimmy pitched and won the State Little League Tournament at the Northern League Field in Huntsville. The team went on to compete in the Regional Little League Tournament in St. Petersburg, Florida. Jimmy went on to excel in baseball, basketball, and golf at Butler High School. His senior year, the Butler basketball team won the City Title and finished second at the State Tournament. Also during his senior year, Jimmy pitched a 1-0 win for the Butler baseball team over Huffman High School in the Regional Tournament. Jimmy signed a baseball scholarship to Clemson University, and pitched for 3 years before being drafted by the Toronto Blue Jays Major League baseball club. Jimmy was traded to the New York Yankees where in 1996 he pitched in the Yankees World Series victory over the Atlanta Braves.