It was brought up how to let a Heel win it cleanly and remain a Heel that has not been used before, Well I have an Idea. This would only work for Edge or Kennedy. You keep them both off TV (yes this will be tough) until Royal Rumble and let one of them show up with a mid pick in the 20's. Everyone will think that that person will win. Then #28 or #29 hits and A top face music plays (Rey Mysterio, Matt Hardy, Jeff Hardy, ...) and then no one comes out. The titan tron shows them beat and bloodied and all of a sudden Either Kennedy or Edge runs down with a plastic ball containing the number 28 or 29 in thier hands, gives it to a referee and then cleans house and wins. It would be a clean win because there would be no going out of the ring and back in or landing on one foot at all, just entering in a slimy way and at the same time eliminating another top contender, it could even lead to a fued between the Heel winner and the face he took out. NOW that would be a way for everyone to hate the winner!!!!
This is a logical way to get that person in the rumble, but how would you have them eliminate all the people in the ring already?
I think there are two good ways to have this happen.
1. Following your plan, have all the good faces (credible winners) enter early. Have the one that gets taken out backstage enter really late, like 28-30. Thus, the heel would be the latest credible entry to win. Have all the faces he eliminates to win be really exhausted from entering in single digits. Thus, he didn't beat 'fresh' faces, but worn down faces. It diminishes the heel's win, but gets him the win regardless. A feud with the guy he took out would obviously happen, but shouldn't last more than a month going into Wrestlemania.
2. Have a credible face be the only man in the ring BEFORE #30 comes out. Have him worn out and beat up, but ready to face #30. Have #30 be a face too, but not the top face in the rumble. (Ex. Have Cena in the ring with Hardy to enter.) Then, after the heel (I'll say Edge) takes out Hardy for his number, it would be a worn down face (Cena) VS a fresh heel (Edge) for the shot at Mania. Simply put the heel over on the fact that the face is worn out. Play the time card, like "OMG, he's been in there for 45 minutes" or something, to make the loss more acceptable.
The only other way to make a credible heel win last as a heel superstar is to challenge a face champion. You need a really over face champion that no one wants to see lose against a sneaky heel. The heel can win the rumble clean, and then resort to heel tactics afterward. It would have to happen to maintain the heel status.
However, to really play this out well, a heel should lose his title to a face at the rumble event itself. The face will celebrate the win afterward, and the new heel that won the rumble crashes the party.
These are all just some random ideas I have on the subject, but I appreciate the idea of a heel winning something clean. Too often are we cheated of a clean finish to a match we may never see happen again.