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I've gone on about this before, but I'll say this again:
The key to making a character successful is to make people CARE.
People see Orlando Jordan, and yes he gets heel heat, but the majority of people don't care about him. If he came out next week on SmackDown! and said he was retiring, I'd be one of the few people who would be saddened by this news.
If Jericho came out on RAW and did the same thing, people would probably breakdown right there and then. Why? Because people care about Y2J.
So how do you make people care about Orlando Jordan? Well, there must be plenty of ways, but I'd do this:
Leading up to WrestleMania (JBL vs. Cena) have JBL start piping the flute of everyone in his Cabinet (as per usual). JBL then wins a WWE United States Championship open contract (maybe he can pay Vince McMahon for it or something at the Rumble). Have JBL give the US Title shot to Doug Basham, and have the match take place at No Way Out (Cena and Doug are fairly familiar with each other, so I think we'd see a great match-up).
This causes tension, because even though he's already a WWE Tag Team Champion, JBL gives the US Title shot to Doug, which Orlando confronts JBL about. JBL then says he needs someone who can get the job done, and Orlando is a great athelete, but it takes more than a great athlete to defeat Cena, and OJ still has a lot to learn.
At No Way Out, have John Cena retain the WWE United States Championship, then have Orlando tell JBL he could have gotten the job done. JBL just laughs.
You then have JBL retain the WWE Championship in the Barbed Wire Cage Match, and have JBL give a speech thanking his Image Consultant, Amy Weber and some other inspriation to is life (I dunno, George W. or someone), which leads to Orlando Jordan reflecting his decision to join JBL. He looks back at when Booker T called him a houseboy. You have look back on how he betrayed a man who taught him about respect in The Undertaker.
At WrestleMania, Orlando Jordan is in JBL's corner per usual, and Cena and JBL do their stuff, and we see the ref get knocked down. JBL asks Orlando for some help. Orlando gets in, and hits JBL with a right hand (play up his boxing background), and have JBL sell it like he just got hit by the ring bell. Orlando then gets the WWE Championship, then uses it to keep The Bashams at bay, while Cena hits an F-U. 1-2-3, John Cena is the WWE Champion.
That's OJ's own little WrestleMania moment, and it may not sound good now, but I think if they did it right, Orlando breaking out of the chains JBL has latched onto him would make for a great turn of events. You don't even need Orlando to turn face, just have him take over JBL's Cabinet as its new leader. JBL can then go to RAW in some sort of continuation of his character.
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