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As pretty much every wrestling fan knows, Ric Flair is considered a 16 time world champion by WWE. However, it's less well known that this number has been disputed. If you take a look at his Wikipedia page, there's 19 in total: 9 NWA, 8 WCW, and 2 WWF.
Benoit held 22 championships between WWF/WWE, WCW, NJPW, and ECW. He was a two-time world champion, having been a one-time WCW World Heavyweight Champion, and a one-time World Heavyweight Champion in WWE; he was booked to win a third world championship at a WWE event on the night of his death.