Listed as 6 feet 2 inches (1.88 metres) tall and 190 pounds (86 kilograms), Jim Bailey attended Lincoln Memorial University and signed with Cincinnati in 1956. He was recalled by the Reds after spending four seasons in their farm system.
In three MLBgames pitched, Bailey posted a 0–1 record with seven strikeouts and a 6.17 ERA, allowing 17 hits and six bases on balls in 11⅔ innings, including one start. The start coincided with his MLB debut, September 10, 1959, at Wrigley Field against the Chicago Cubs. With brother Ed catching for him, the rookiesouthpaw pitched well into the eighth inning, with only three earned runs allowed, but then surrendered three more runs to Chicago, pinning him with the 6–3 loss.[1]
Bailey retired from pro ball in 1961 after a six-year career.