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Rico defeats Ric Flair (September 16th, 2002) 

Photo Credit: WWE

With the greatest sideburns this side of Martin Van Buren, OVW stand-out Rico Costantino debuted on TV as a heavily-implied homosexual, managing Billy and Chuck. The flamboyant stylist had won the SmackDown Tag Team titles and had shared the ring with some clear stars, but he was just there for some classic WWE ‘comedy’ – by which I mean WWE’s ‘different = weird and funny’. 

After Rico had been involved in the invading Raw assault of Billy and Chuck’s SmackDown wedding, the eccentric character was offered a slot on the Raw roster. Immediately making a mark, Rico managed to get a pinfall win over Ric Flair. 

Around this time, Flair was still having confidence issues, having lost his mojo not too long before. This was reflected on-screen with ‘The Nature Boy’ having floundered after losing his role as General Manager. In this, a seemingly unfocused Flair refused to cheat by using a chair before being hit with a roundhouse heel kick. Despite the ex-NWA star’s hand being on the rope, the pin counted, with the crowd and announcers alike seemingly baffled by the result as Rico beat the multi-time world champion in less than 4 minutes.

This was a very significant moment – serving a very important purpose. It showed Flair’s further downfall, with Triple H berating Ric for his loss after the match. This would build to Flair joining up with ‘The Game’ to set up the Evolution stable, who would dominate the WWE for the next few years.  

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