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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.
The World Heavyweight Championship was brought to Raw by former General Manager Eric Bischoff after WWE Champion Brock Lesnar became exclusive to SmackDown. Bischoff awarded the championship to Triple H, but The Game had to defend it against his best friend, Ric Flair. Triple H was successful and has held the championship on five different occasions. Other holders of this prestigious championship include Shawn Michaels, The Undertaker and Rey Mysterio.