Robert Sherwood "Bob" Bailey (born October 13, 1942) is an American former professional baseball third baseman. He played seventeen seasons in Major League Baseball (MLB) between 1962 and 1978 for the Pittsburgh Pirates, Los Angeles Dodgers, Montreal Expos, Cincinnati Reds, and Boston Red Sox. Bailey attended Wilson Classical High School, where he was the 1961 CIF Baseball Player of the Year and quarterbacked the football team for two years, one of which was undefeated. He was originally signed by the Pittsburgh Pirates as a bonus baby.
In a 17-season career, Bailey posted a .257 batting average with 189 home runs and 773 Runs batted in in 1931 games played.
After his playing days were over, Bailey was a minor league manager and hitting instructor, most notably in the Montreal Expos organization. In 1987, he was the final manager of the Hawaii Islanders.