Benjamin attended River Ridge High School in New Port Richey, Florida, where he lettered in both football and baseball.
[1] Benjamin signed with the Tampa Bay Buccaneers as an undrafted free agent following the 2001 NFL draft.
He was also a member of the New England Patriots that offseason and played one game for the Chicago Bears in place of an injured Patrick Mannelly.
The next season, he would temporarily be back with the New England Patriots before being re-signed by the Buccaneers and winning in Super Bowl XXXVII.
While at USF, he majored in political science and was the head coach at River Ridge High School through the 2021 fall season.