Year: 2008

Does it get any more embarrassing than this story? After spending the night out at a Brazilian club, former AC Milan striker Ronaldo de Nazario brought home a few ladies for what he thought was going to be a wild evening. It certainly was, just not in the way that Ronaldo probably expected. The women accompanying him actually turned out to be transvestites and Ronaldo, so horrified by his mistake, asked them to leave and offered money to keep them quiet. But when they started asking for too much in return, Ronaldo refused to negotiate, and the prostitutes leaked the story to the press. Just try and name a worse way to get caught with your pants down.