The most memorable moment of Jim Duggans career that I can remember, was him getting demolished by Yokozuna on Monday Night Raw. He laid him out, put the American flag over his body, and Banzai dropped him a couple times if I remember correctly. That's the big highlight of his career, because no one ever really gave a shit that he won the first Royal Rumble.
Ultimate Warrior could easily go DEEP in this tournament because there's never really been anyone as dominant as him for any period of time. This guy just wrecked em' and kept going to the next poor victim. The power of the Warriors is far too much for Duggan or virtually anyone else to overcome. Warrior wins this one by flexing his muscles in front of Duggan, who then shits his pants and runs to the back to change them, losing by count out.