Milton turned professional in 1985 and won his first five bouts before losing a split decision to future title challenger Ismael Negron. Then managed by Jim Wiley, who managed Milton and other members of what was coined the “Hudson County Express” including Mark Medal, Alphonso Bailey and Robert “Pee Wee” Rucker, Milton took another significant stepback in 1987 when he was stopped after five rounds by Angel Sindo. Now deemed a “stepping stone,” Milton went on the best run of his career in 1989, defeating the 11-1-1 Pedro Rivera, then handing future world champion Gerald McClellan his first pro defeat by majority decision, before closing out the year with decision wins over contenders Robbie Sims and Olajide.