The Tampa Bay Buccaneers entered into the NFL in 1976 and promptly lost their first 26 games. Talk about foreshadowing. 

Things haven't always been gloomy, though. Head coach Jon Gruden was traded by the late, great Al Davis for the tune of four draft picks. Gruden led the team Tony Dungy had built to win Super Bowl XXXVII, ironically, against the Oakland Raiders.