I find it difficult to keep it to 5 so I'll categorize. Most need no explaination.
NFL Owners:
Jerry Jones
Daniel Snyder
Al Davis
NFL Coaches:
Bill Billycheat
Brian "the brain" Billick
Mike Holmgrem
Jack Del Rio
Mike Shanahan
NFL Players:
Housh & the Douche (Douche = Chad)
Ray-Ray
Bruschi
T.O.
Kellen Winslow
Eli (for being a cry-baby when drafted by San Diego)
Anyone who puts on a Raiders, Ravens, Browns, Bengals, Cowboys or Patriots Uniform
Retired Players:
Michael Irvin
Shannon Sharpe
Emmitt Smith
Non-football related:
Fransisco Cabrera
Billy Volek
The list continues, that's just off the top of my head.
Following chaos' rubric:
Owners:
Jerry Jones
Bob Kraft
Fart Modell (I know he's gone, but, c'mon)
Coaches:
Bilge Ballachimp
Billick
Holmgren
Coughlin
Players:
Beardy
Bruschi
Harrison
Ellie Manning
That retard on the Cincy line biting Polamalu's hairstyle
Plastico
Retired:
Romanowski
Smellway (funny how the hissy fit to start his career has been airbrushed from history)
Cliff Harris
Posters here:
Captain Chaos, for bringing up
David Volek