He was signed out of high school by the
Pittsburgh Pirates as a
bonus baby and made his debut with the Pirates at age 19. After the 1966 season, the Pirates traded Bailey and
Gene Michael to the
Los Angeles Dodgers for
Maury Wills. The Dodgers sold Bailey to the expansion
Montreal Expos following the 1968 season and he became a fixture in the Montreal lineup. He batted fifth in the inaugural game of the Expos versus the New York Mets on April 8, 1969, going 2-for-4 with two RBIs and one walk in the 11-10 win. The
Cincinnati Reds acquired Bailey from the Expos for
Clay Kirby on December 12, 1975, and he was a member of the Reds team that swept the
New York Yankees in the
1976 World Series. In a 17-season career, Bailey posted a .257
batting average with 189
home runs and 773
Runs batted in in 1931
games played. He led the
National League in
Double Plays turned by a
Third baseman in 1963, Double Plays turned by a
Left fielder in 1974 and
Fielding percentage by a Third baseman in 1971. Bailey struck out on three pitches against
Goose Gossage in his final plate appearance for the Boston Red Sox against the Yankees in the
1978 American League East tie-breaker game. With no out and one on in the bottom of the seventh, Bailey pinch-hit for
Jack Brohamer in what proved to be a massive tactical error by Red Sox manager
Don Zimmer. Zimmer expected the right-handed Bailey to face left-handed Yankees ace
Ron Guidry, so Zimmer sent Bailey into the on-deck circle. Instead, Yankees manager
Bob Lemon brought in the right-handed Gossage, and since Bailey had been announced as the pinch-hitter for the left-handed Brohamer, plate umpire
Don Denkinger told Zimmer he could not recall Bailey and put Brohamer back in. The Red Sox lost 5-4. ==Later life==