#2. Not a genius - Trying to make Lex Luger and Diesel the next Hulk Hogan
Vince McMahon tried on numerous occasions to replace Hulk Hogan as the face of the company and he failed on each and every attempt. He first tried to make The Ultimate Warrior as the face of WWE, even having him go over Hogan.
However, the Warrior didn't draw as expected and McMahon was forced to return to Hogan. Warrior had high levels of popularity, so the decision to try and make him the face of WWE was understandable. Not so much in the next two attempts.
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He first tried to push Lex Luger to the moon, but it didn't work because he had suddenly changed from a nefarious heel to a patriotic hero. Not only was his character not believable, but Bret Hart's rising popularity made McMahon push the Canadian star instead.
His second attempt was Diesel, where he gave Kevin Nash a near full-year reign as WWE Champion. Unfortunately, he turned out to be the lowest drawing champion in WWE history and Bret Hart would win the title back just shy of a year later. Neither Luger nor Diesel possessed the charisma to replace Hogan.
Once Hogan, Bret Hart, Nash and Lex left for the WCW, the WWE needed a new breed of superstars to carry the brand forward. Vince smartly invested in The Rock and Stone Cold to spearhead the cause and it did wonders, helping the brand claim bragging rights amongst other promotions.