1. May 23, 1999: Over The Edge & Owen Hart's Death
If there was ever a reason for people to hate Vince McMahon, it would be his decision to go on with the show at Over the Edge after Owen Hart passed away. When Owens safety harness for his special entrance failed, he fell 78 feet (24 meters) and landed chest-first on the top rope, almost hitting the turnbuckle as well as referee Jimmy Korderas. Wrestlers were in different moods altogether, and Jim Ross somberly announced to the audience that was happened was very real. Tragically, Owen was pronounced dead by the time he reached the hospital. The cause of death was internal bleeding from blunt-force trauma. The Hart family sued WWF, eventually settling for $18 million. Vince has received scathing criticism for allowing Over the Edge to continue, making the dubious claim that its what Owen wouldve wanted. Despite the event being retired, virtually everyone agreed that Vinces decision was just some poor ploy to maintain a ratings advantage over WCW. This was one of those moments where wrestling was really getting negative publicity in the most poignant of ways. Owen Hart was a young man of 34, with a wife and two young children. They had to grow up without their father and their mother constantly in court, fighting WWF and Vince McMahon over what was deservedly their compensation for what many have called an unnecessary, overcomplicated and dangerous stunt. It should come as no surprise that Vince is probably wracked with guilt over Owens death and the dubious decision to continue the show that night. This is one night that Vince will never, ever forget.