Bolden was born and grew up in Cleveland, Ohio and attended Glenville High School.
He did not join the school's football team until his junior year and became the Tarblooders' starting quarterback, passing for 2,800 yards and 31 touchdowns in two seasons.
[1] Bolden was a member of the Toledo Rockets for five seasons, redshirting as a freshman.
[2] In his senior season he was named second team All-MAC after completing 214-of-319 pass attempts for a then-MAC record 67.1% completion percentage and 2,466 yards with 13 touchdowns and also rushed for 335 yards and four touchdowns.
[4] Bolden was signed by the Montreal Alouettes of the Canadian Football League (CFL) on April 24, 2002.