20. Dallas Cowboys
‘America’s Team’ is traditionally one of the biggest and most valuable franchises in the country. But this doesn’t necessarily translate to success on the playing field. The five-time Super Bowl winners haven’t held the Vince Lombardi Trophy since 1995. But since then it’s been misery after misery for one of the most iconic teams in the entire nation. It’s almost sad to watch.
Currently, they have one of the worst defenses in the league and severe quarterback issues. Meanwhile, the front office needs to take some responsibility and create a coherent plan because that has allowed a loser’s mentality to take center stage. They want to win but they keep grabbing handfuls of sand that inevitably slip through their fingers. In sum, eight winning seasons since their last Super Bowl win is horrendous.