I would love to see Delonte come back here. I like his game, he can shoot almost as well as House, he can handle the ball much better, and he plays better defense. Problem is, we won't be able to offer him anything substantial if Posey resigns. Under that scenario, we could only offer an LLE deal starting at 1.9 million. He won't take a long term deal at that rate, and Cleveland would most definitely match that anyway (I think his qualifying offer, which I'm sure they extended, is a million higher than that anyway). Plus, I agree, he's probably as well off in Cleveland as he would be here, at least in the short run.
But in the long run, why would he want to stay in Cleveland? There is no way you can count on Lebron returning to the Cavs after 09-10. The Nets will have room for a max contract, and the Knicks will do everything they can to do the same. He's going to leave. And at that point - the Cavs will be a mess. They'll have money (their only current salary for 2010-11 is Lebron's player option), but nobody to spend it on. Who's gonna want to come to Cleveland after Lebron leaves?
I don't think we can or will get Delonte this season because of financial constraints. My personal hope would be that he goes back to Cleveland on a one year contract at the qualifying offer rate, and next year, we can persuade him to come to Boston with a deal using the MLE. At that point, Cleveland won't be able to match, we'll have the MLE available, the "Lebron is leaving" rumors will be even more powerful, to the point I wouldn't be surprised if the Cavs traded him during that season to try to get something of value when he leaves. So, Delonte might be willing and ready to move on and try to take a shot at a title here. I think he liked it here, and I hope we'd be happy to have him back, I think he's great. But I think it's a year before we can realistically talk about taking a shot at him.