Bailey prepped at Beckley Stratton before going out West to Long Beach (California) Junior College. While there, Bailey was named to the All-State Junior College team in a state where junior colleges are strong. He led Long Beach to 60 wins in 64 games, averaging 17 points and 16 rebounds. His jumping ability intimidated shooters as he blocked 80 shots in 27 games. He also set a school record with 37 rebounds in one game. His single season scoring high was 32 points, as he made 13 of 19 from the floor. Bailey was MVP in the Los Angeles Metropolitan Conference both years at Long Beach.
He transferred to West Virginia for the 1968 season. It was believed that his rebounding strength could be his biggest contribution as he was being depended on to pick up the slack of departed Bob Benfield and Carl Head. He led the team in rebounding with 295 and ranked second in scoring to All-American Ron Williams with a 13.9 average. Bailey had also gained a reputation for his tremendous jumping ability (it was said that he could touch the top of the backboard, 13 feet high).