Randolph Gassaway graduated from Riverwood International Charter in 2013. Out of High School, Randolph was Drafted by the Baltimore Orioles in 2013 MLB Draft where he played 6 seasons reaching AA in 2017. During his time with the Orioles, Randolph was named to the Carolina League All-Star Game in 2017. After 6 years with Baltimore, he was selected by the Pittsburgh Pirates in the 2018 Minor League Rule 5 Draft.
Coach Randolph Gassaway specializes in Hitting, 1B, and OF. For the 2020-2021 season, Randolph will be coaching with the Georgia Bombers 14U and 16U teams alongside Jordan Hill and Wes Rynders.