Raised in Roselle, New Jersey, Miles played prep football on both offense and defence at Abraham Clark High School.

Miles was drafted by the Pittsburgh Steelers in 1995, but failed to make the team after suffering a serious knee injury in a preseason game versus the Buffalo Bills during his rookie season.

Miles joined the Montreal Alouettes in 1998, and made an immediate impact, winning the CFL East Division Rookie of the Year Award.

Miles played seven seasons with Montreal, and was named a CFL All-Star three times (1999, 2000, 2002) during his tenure as a Lark.

Miles also notched one defensive tackle, a blocked kick, and a quarterback sack in the Lions' CFL West Division Championship game against the Saskatchewan Roughriders, as well as three defensive tackles in the Lions' 25-14 Grey Cup Championship victory over Miles' old team, the Montreal Alouettes.