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Short of a stupid, clichéd answer like "Vince McMahon" there is no single problem.
Wrestlers don't seem to raise the bar, but booking seems stagnant, and advancement seems minimal. So on both ends of that, you've got problems. No plans from creative, no incentive for the wrestlers.
This can be relegated in part to politics, but part of it is Vince doesn't know how to book a show that entertains the masses, and has hired staff that writes along the lines of what Vince likes. A lot of people are booked strong, but dropped altogether when booking/Vince/whatever gets bored with them. Vince thinks Cena and Batista are the future, and will continue to push that until they die, are injured, or the ratings completely tank.
In the current business, you're pretty much either "made" or you're not. It's clear, for example, that Orton will be a main eventer no matter how many times he fucks up. That was clear early on. You can say he can't wrestle, he can't talk, but he's a made man. When they're keen on someone, when they like someone, they will go "far," like it or not. When they're not...
...Well, Christian comes to mind.
That's not really holding people down, and so I think it's a separate issue. It's still politics (Who you know, who you're related to, etc.), it's just not say, Triple H holding down the roster. Cena's arguably done more damage to the actual roster than Trips ever did.
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