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The first Money in the Bank ladder match was at Wrestlemania 21, the winner of that match Edge. He used the contract at the 2006 pay per view New Year's Revolution, defeating WWE Champion John Cena.
Flair won his first title in WWE in Jan 1992 at the Royal Rumble Pay Per View in Albany New York. It was for World Heavyweight Title
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He was in Tough Enough, before he was in Tough Enough he was a cast member for The Real World: Back to New York.