Major League Career
Born in Strawberry Plains, Tennessee, Bailey was contracted by the Cincinnati Redlegs in 1950 as an amateur free agent. He reached the Majors in 1953 and in 1955 he was given a chance as the Reds' starting catcher, replacing Andy Seminick. When his offensive production floundered, the Reds traded Seminick for catcher Smoky Burgess and Bailey was sent down to the San Diego Padres of the Pacific Coast League. With the help of some batting advice from Reds manager and former catcher Birdie Tebbetts, his hitting improved in the minor leagues and continued to improve in the Venezuelan Winter League.
Bailey began the 1956 season as the backup catcher to Burgess, but when the team faltered early in the season, Tebbetts decided to shake things up and named Bailey as the Reds' starting catcher. By mid-season, he was the leading hitter in the National League with a .335 batting average, helping to spur the Reds into first place. His hitting performance earned him a place as the starting catcher for the National League in the 1956 All-Star Game. The Reds stayed in the pennant race until the last day of the season, ending up with a 91–63 record, two games behind the Brooklyn Dodgers. Bailey ended the 1956 season with career-highs in batting average (.300), home runs (28), runs batted in (75), and led the league in baserunners caught stealing (23).
In 1957, the Reds were once again in first place at mid-season, but faltered to finish the season in fourth place. Bailey earned his second consecutive start for the National League All-Star Team, led National League catchers with a 46.2 Caught Stealing percentage and finished second to Roy Campanella with a .992 fielding percentage. He remained as the Reds' starting catcher for the rest of the 1950s up until twelve games into the 1961 season, when he was traded to the San Francisco Giants for catcher Bob Schmidt.
In 1962, Bailey platooned with catcher Tom Haller, as the two players combined to give the Giants 35 home runs and 100 runs batted in from the catcher's position. In June of that year, Bailey had a streak of 3 clutch home runs in four games that propelled the Giants into first place. The Giants battled the Los Angeles Dodgers in a tight pennant race as the two teams ended the season tied for first place and met in the 1962 National League tie-breaker series. The Giants won the three-game series to clinch the National League championship. Bailey appeared in six games of the 1962 World Series, hitting a home run in Game 3 as the Giants lost to the New York Yankees in seven games. He had another strong year in 1963, hitting 21 home runs with 68 runs batted in, earning his fifth and final All-Star berth.
In December 1963, Bailey was traded along with Felipe Alou and Billy Hoeft to the Milwaukee Braves for Del Crandall, Bob Hendley and Bob Shaw. He served as Joe Torre's back up for two seasons with the Braves before being traded back to the Giants in February 1965. After just fourteen games of the 1965 season, he was traded again, this time to the Chicago Cubs, where he served as a backup catcher to Vic Roznovsky. On July 22, 1965, Bailey hit a grand slam home run, a three-run home run and a run-scoring single to drive home eight runs during a game against the Philadelphia Phillies. After the 1965 season, he was traded to the California Angels and was released after appearing in only five games of the 1966 season.
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