He started his football career in high school at Woodbridge College, where he was a York Region and GTA all star at quarterback and safety.

[8] In high school, Bradfield was named the most valuable player of the basketball, football, volleyball, baseball, and tennis teams.

[9][10] Bradfield was also an Ontario Varsity Football League (OVFL) all-star receiver as a member of the Etobicoke Eagles.

[13] That statistic also etched Bradfield into the CIS record book at 6th all time for punt return yards in a single season (734).

Bradfield also goes down in the Toronto Varsity Blues record books as second all time in kickoff return yardage in both a single season and career.