Whitehead began his pro career signing as an undrafted free agent with the San Francisco 49ers for the 1995 season.
After being cut by the 49ers, he split time between the CFL's Baltimore Stallions active roster and the 49ers practice squad.
The following season, he played with the CFL's Montreal Alouettes and then in 1997 he led the Hamilton Tiger-Cats in sacks and added 44 tackles.
After his strong showing in the CFL, Whitehead spent the 1998 training camp with the Detroit Lions before having a brief stint with the Frankfurt Galaxy of NFL Europe.
Whitehead along with Ira Newble appeared together on an episode of The Real Housewives of Atlanta where they were dates at an auction.