Willingham was also a member of the Dallas Cowboys, Seattle Seahawks, Cincinnati Bengals, and New England Patriots.

Willingham attended Calhoun County High School in St. Matthews, South Carolina, where he was a three-year starter at defensive back, wide receiver, and kick returner.

After going undrafted in the 2009 NFL draft, Willingham signed with the Tampa Bay Buccaneers.

Willingham was claimed off waivers by the Dallas Cowboys on August 30, 2009; however, he was waived during the team's final cuts six days later.

On November 3, 2009, the Seattle Seahawks signed Willingham to their practice squad, where he spent the remainder of the season.