3. Mark Henry - $250,000 Per Year, Ten Year Contract In 1996
WWE signing Mark Henry in 1996 was a huge thing. For one, they rarely offered any guaranteed contracts back then. For two, they were giving a weight-lifter $250,000 to become a wrestler, on a sensationally long ten year contract. They didn't even know if the guy could wrestle. It was madness. This was also back in a time when WWE's financial health wasn't too great. It was the same year they let Nash go, based on the idea they couldn't afford top guys at the $750,000 rate WCW offered. But they could afford a completely unproven guy like Henry at $250,000? McMahon must have been crazy! Henry flopped spectacularly, taking over a decade to start having decent matches. He still works with WWE, and is fairly good now, but he was so bad in those early years. WWE stretched their financial resources to the max to get him, and looking back even McMahon must admit it wasn't worth it.