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For it to work, firstly I think the old crew should be the heels (which was the first mistake WCW made. How can a group called "The Millionairres Club" be faces, for fuck's sake?)
Secondly, the younger crew should be made to look, for the most part, superior... superior athleticism, superior ability, more wins than losses etc.
Thirdly, ultimately the "next generation" group should eventually win the feud.
And those three reasons are why it will never happen or never work.
...Unless, of course, Triple H were to decide that DX are still super-cool, young rebels and join the YOUNGER stable (which would make no sense, but is quite feasible that he would think like that) in which case they might stand a chance of winning, but lose all credibility.
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