Bolling was a two-sport athlete on The Hill playing both baseball and basketball before signing a professional baseball contract after the 1951 baseball season. He was a key member for two seasons with the Badger basketball team from 1949-51. He helped the team to a 15-12 season, the 1950 NAIA District tournament and 1951 Gulf States Conference Championship. On the diamond, Bolling was a standout 2^nd baseman, hitting .368 in 1950 and .431 during the 1951 season. After a stint in the military during the Korean War, he went on to a spectacular 12-year Major League career with the Detroit Tigers and the Milwaukee Braves. He was a voted to the National League All-Star Team in 1961 and ’62 while earning a Gold Glove with the Tigers in 1958. Bolling and his older brother Milt, who is also a member of the SHC Hall of Fame, teamed up for Detroit as one of only four brother pairs to play together in the Major Leagues. Bolling has been honored in Milwaukee as part of the Braves ring of honor and is also a member of the Mobile Sports Hall of Fame. There is also Bolling Brothers Drive in Mobile leading to Hank Aaron Stadium.