Russ rarely entertains the idea he could fail at whatever it is he's trying to do. He tried to extort a date from Taylor by saying she could either go on a date with him (the infamous red dress post) or he would win the $80 million lawsuit against her. He just assumed he would win. When he lost to Skordas both times, he was quite stunned because he didn't actually believe he could lose. He was convinced for months afterward that if he'd just been allowed to show his blurry pic of a security guard, he would have won.