Nicknamed "Jammin' James," he spent 9 seasons (1979–1988) in the National Basketball Association (NBA), playing for the Sonics as well as the New Jersey Nets, Houston Rockets, New York Knicks, and Phoenix Suns.

While at Rutgers, Bailey was a formidable player, displaying a strong inside presence in addition to possessing great leaping ability.

The rule allowing dunking was re-instituted in college basketball beginning with the 1976–77 season, Bailey's sophomore year.

The Scarlet Knights advanced to the NCAA basketball Final Four in 1976, Bailey's freshman year, arriving with a 31–0 record.

Bailey is number three on the Rutgers all-time scoring list (2,034 points),[1] and second in career rebounds behind Phil Sellers (1,047).