Here's a simple trade that might make sense for two teams.
Ben Gordon for Anderson Varejao.
Gordon would be a little redundant playing alongside Mo Williams. Be giving up a little size, although probably not much worse than when they play Delonte and Mo together. Cleveland's real issue is that they don't have ANYONE who can create their own shot, and they don't have a real point guard who can create shots for someone else. Ben Gordon wouldn't solve the need for a legit point guard, but he can create his own shot, he can handle much of the scoring load for them.
If Cleveland can get lucky and find a legit, starting-caliber PG, Mo Williams would be perfect off the bench.
Cleveland would need a center, don't think you'd want Jamison playing there. Maybe Hickson, a little bit? Cleveland would still have the MLE, probably go after Brad Miller with it (hopefully for no more that two years.
For Detroit, they just signed Gordon last year, and probably aren't ready to give him up yet. As we've known since that signing, they have way too much overlap at the wings, with Gordon, Rip, Prince, and Stuckey (who ain't a PG, either). They'd love to get rid of Rip, but nobody's biting on that contract.
And... they pretty desperately need a center. Ben Wallace will be back, but he's year-by-year now. You couldn't play Wallace and Varejao together, but you could give Andy 30 minutes and Ben 18 and be in decent shape. When Ben finally hangs them up for good (or signs in Boston

), they'll have a decent 5.
Alternatively, a crap-for-crap trade, they might think about a Rip-for-Mo deal. One bad contract for another. Mo's not a natural PG, but he's closer to being a 1 than Stuckey or Gordon. Detroit could start Mo, Gordon, and Prince, with Stuckey off the bench, and be in OK shape. Rip Hamilton's not nearly as good a player as he once was, but he's a little bigger and I think a little better fit in Cleveland. This assumes that you're keeping Delonte around, and he'll start at the point (an issue to be resolved on a later day).