5. Big Show - $1 Million Per Year, Ten Year Contract In 1999
Paul Wight was disillusioned and wanted out of WCW in 1999, allowing his contract to expire. But he still wasn't going to come cheap. The WWF had to cough up a ten year contract with a million dollars per a year to secure his services. Why did they pay so much? The answer is because Vince McMahon was a mark for The Giant. He loved huge performers and saw the second coming of Andre. It was a bank breaking contract in the fact that WWE weren't in the business of offering such huge money right off the bat. They were also against offering such long deals, but McMahon really wanted the big guy. Show did have some leverage, including a hollywood career and potentially more money from WCW. In the end McMahon got the deal done, signing a performer who continues to work for him to this day.