Leon Lett
Lett was a two-time Super Bowl winner with the Dallas Cowboys but that’s not why fans remember him. He made two career-defining mistakes that made him a figure of ridicule. First, there was his infamous fumble against the Bills as he approached the endzone. Luckily it didn’t cost his team the game.
Then there was another embarrassing incident during a Thanksgiving game. Lett bizarrely caused a ‘muffed kick’ in snowy and surreal conditions. Many fans don’t respect him because he made high-profile errors, but ultimately he was a winner with the Cowboys (via NPR).