Bailey signed with the Pirates for what was believed to be a record bonus of $175,000 in 1961. He was TSN Minor League Player of the Year in 1962 and the regular Pirate third baseman for the next four years. The Dodgers traded Maury Wills for Bailey and Gene Michael in December 1966, but Bailey hit only .227 for two consecutive years, and Los Angeles sold him to the expansion Expos.
Bailey hit well for the Expos. Manager Gene Mauch often said: “Bailey means wood. Bailey doesn’t mean leather.” An opponent added: “They called him Beetle, after the comic strip character. He fielded like a comic strip character.” As the starting third baseman in 1972-73, he made 39 errors. Mauch also tried him at 1B and OF.
The Montreal fans developed a love-hate relationship with the slow-footed streak hitter who grounded into 216 lifetime double plays. In 1970 Bailey hit .287 with 28 homers, including one of the longest shots in Astrodome history on August 16. When he was traded in December 1975, he was the leader in nine of ten Expo career batting categories.