Robert Sherwood Bailey (October 13, 1942 – January 9, 2018) was an American professional baseball third baseman.

Bailey attended Wilson Classical High School, where he was the 1961 CIF Baseball Player of the Year.

[1] After the 1966 season, the Pirates traded Bailey and Gene Michael to the Los Angeles Dodgers for Maury Wills.

Bailey batted fifth in the inaugural game of the Montreal 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.

[4] After his playing days were over, Bailey was a minor league manager and hitting instructor, most notably in the Montreal Expos organization.