2. Gorilla Monsoon Legit Won $11,000 During WrestleMania Segment
Both WrestleMania IV and V were held in The Trump Plaza casino complex in Atlantic City, New Jersey. The venue held around 20,000 fans, but was a popular destination for the company. Vince McMahon had become good friends with Donald Trump, meaning it was a deal that suited both parties. It also suited those in the WWF who liked to gamble. During the weekend of 'Mania V, Gorilla Monsoon and Bobby Heenan went to one of the casinos to film segments for Prime Time Wrestling. Whilst there, they had planned to pretend to play some of the games, creating entertaining scenarios. One of the staff informed them that it was against house rules to pretend, so they would have to actually gamble. Incredibly, without really concentrating on what he was doing, Gorilla Monsoon bagged himself a major win during filming. Focusing more on his chemistry with Heenan, Monsoon pocketed $11,000 whilst the cameras were rolling. He decided to leave a $300 tip for one of the staff, because it had been their suggestion that the announcers actually play.