This was the match I was hoping for since the start of this tournament. You have two of the most charismatic wrestlers in the history of the business. While I recognize that due to his overwhelming popularity and the median age of the poster who visits this forum, Flair's chance of winning this match up fall somewhere in between "slim" and "none." My hope is to give you the reasons, kayfabe and otherwise, why this should lean heavily in Flair's favor.
Now, let me preface this perspective with the declaration - I am a HUGE fan of The Rock. Anyone who knows me knows that he's in my personal top 5 favorite wrestlers ever. During my formative years as a fan, while Flair's NWA and subsequent WCW were still my preferred viewing choice, the only thing that piqued my interest on the USA Network was The Rock. In many respects, I actually viewed The Rock as the natural successor to Flair as the top guy of his generation on the microphone; his persona also fit that particular bill to a tee. While Rock's character has evolved to include many facets and reflections of his actual personality, his original (and by original, I don't mean "Rocky Maivia") persona (during 97-99) was actually closer to Flair's "Nature Boy" then some even give it credit for. Mike Mooneyham of the Charlotte Post Courier wrote in his book "Sex, Lies and Headlocks" (great read, BTW) that the influences were undeniable. Whether it was "$500 Versace shirts" for the people's champion or "$10,000 suites from Michael's in Kansas City," stylin' and profilin' was on the agenda for both superstars. You can continue to draw parallels, but the reason I bring them up is to educate those rascally Rock fans who felt as though his character was wholly unique and irreverent. Invariably, there are going to be those "Attitude Era" fans (remind me again what was so magnificant about the booking at that time?) who fail to recognize that The Rock had predecessors who did it first, and more importantly, did it better - that being The Naitch.
On the subject of mic skills and imitation being the sincerest form of flattery, I can hear it now. "Flair suxzz, IF YA SMELLZZZ." Well, if you don't believe me, perhaps you'll take it from an Attitude Era alumni - Triple H said it far better than I could ever hope to: "Before there was a Trail blazing, Eyebrow Raising, Jabroni Beating, Pie Eating, Heart Stopping, Elbow Dropping People's Champion - there was a Limousine Ridin', Jet Flyin', Kiss Stealin' - WOOOOOO - Wheelin' Dealin' Son of a Gun named "The Nature Boy" Ric Flair." Fact is, as great as The Rock is on the stick, he relies far too much on "sing-songy" catchphrases. Are they effective? MY GOD, without question! In terms of crowd participation, The Rock knows how to get his audience involved. Everytime I've seen him live, I was happy to recite back "...AND MILLIONS" or whatever it was he asked of us. Heck, that's half the fun of being there. However, when it comes to the ability to sell the feud - to evoke an emotional response in the hearts of those watching - NONE came close to Ric Flair. Does Ric Flair have catchphrases? Certainly. Were his interviews without substance and filled entirely with them? No. Flair cut promos that served the purpose all promos should - promoted/furthered the feud, promoted the match - and allowed the fan a chance to hate him. Perhaps with the exception of Dusty Rhodes, no one made the promo more of an artform that Flair - not even The Rock.
What about in the ring, you ask? Rock fans will surely sight his resume of having battled the likes of Hulk Hogan, Triple H, Steve Austin and John Cena. Ric Flair's resume DWARFS Dwayne's in every conceivable way. Don't believe me? Pat O'Connor, Harley Race, Jack Brisco, Dory Funk Jr., Ricky Steamboat, Terry Funk, Dusty Rhodes, Randy Savage, Buddy Rodgers, Muta, Giant Baba, Sting, Jerry Lawler, Hulk Hogan - every person who has ever meant anything to this business from 1970 on has stood toe to toe with Ric Flair. Kayfabe or otherwise, Ric Flair in his prime may be the greatest wrestler of all time. Not once have I heard that argument been made for The Rock. While sometimes underestimated and under appreciated, The Rock's psychology, stamina, move set - none of it is on Flair's level. Flair could go 60 minutes with a broomstick and get the broomstick over. There is no environment or gimmick match that Flair doesn't best The Rock. Any variant of the cage match? HIAC, Thunderdome, War Games - Flair has gone the distance with Harley Race, Dusty Rhodes, Triple H, Sting - the list goes on. I am sure a lot of you would be hard pressed to name a memorable cage match involving The Rock. Iron Man match? If I need to explain that one to you, I am truly wasting my time. The TLC match wasn't what I'd hoped for, but even then, Flair would find a way. In his prime, Flair found a way to win - and he'd do the same here.
The fact of the matter is this - in every conceivable way, Ric Flair eclipses The Rock. Yes, even in drawing power. I am sure the statistical analysts will be crawling out of the woodwork on that one, but I stand by the fact that Ric Flair drew consistently for 25 years. Wrap your minds around that - 25 years, the man was a top draw in this industry. Stadium size crowds? An estimated 190,000 in Korea, 50,000 in Texas Stadium vs. Kerry Von Erich - and you can't convince me he didn't aid (and most likely draw a large amount) of the 71,000 that attended Wrestlemania 24. Bryan Alverez of the Figure Four Newsletter ran an article at one point saying that Ric Flair was one of only 3 people to positively affect WCW Nitro's ratings during it's dying days (the other two being Sting and Goldberg). Ric Flair has earned his spot as not just a legend or one of the greatest, but quite frankly, the greatest of all time. So unless the name he's facing is "Hulk Hogan," I really don't think there is an argument otherwise.
Be smart. Vote Flair.