Signed as a third baseman, the 6’5″ Bailey had been catching less than a year when he vaulted from Double-A to Houston in April 1984 to replace an injured Alan Ashby. He homered in three consecutive games from July 15 to 17, and homered from both sides of the plate September 16.
Bailey’s short apprenticeship as a catcher showed as time went on; he couldn’t handle Joe Niekro’s knuckleball, had problems with his mechanics and throwing, and led the NL with 13 errors in 1985. To make matters worse, his shoulder began troubling him in 1986.
Although Bailey was extremely patient at the plate (he had more walks than hits in ’86), he still struck out frequently. He began the 1988 season with Houston, but his declining batting average and increasing weight prompted a demotion to Tucson (Pacific Coast League), and in July he was traded to the Expos’ organization for infielder Casey Candaele. He never played a game for Montreal but resurfaced for short-lived stints with the Giants in 1990 and 1992.