All the "Dion should stay and accept what they give him to win a championship" crap is from people who dont play. Players want to play first (or maximize their money first) which is similar to what we all do in our working lives. If Dion has anything to do with this trade, I respect him for wanting to play. He burns to be on the court. That is great. Being a hanger on to a possible LeBron title in Cleveland is for a soon to be washed up Ray Allen type at the end of his great career, not a kid just starting out trying to create a name for himself.
I agree that the kvetching about what Waiters should do is silly - for one it is by no means clear he has any say in the matter and for two, it's his life not ours.
But, since this is a message board, I will disagree anyway. Being the sixth man for this Cavs team is quite possibly the single best thing that Waiters could do at this time in his career. He's got two more years of his rookie contract anyway, so the money isn't going to matter much in the short term. But he should be able to put up a lot of points and win a lot of games with the Cavs. When he does so, the chances of someone overpaying a high-scoring Sixth Man on a championship or near-championship team are basically 100 percent. Being the second or third option on a terrible team for the next two years is going to accomplish none of that. (And will also further the evolving narrative that he's not a winner, which I'd argue shouldn't matter but almost certainly does.)
I think the wanting to be on the court stuff is kind of silly. He'll play maybe a few less minutes a game for the Cavs but will also play many more games as one team will be in the playoffs and the other in the lottery. Particularly assuming Wiggins and Bennett are out, Waiters seems guaranteed to play a lot of minutes in Cleveland.
(And maybe this is just my personal experience, but I don't buy the analogy to work either - I just took a job with a 50 percent paycut that has some short-term downsides but long-term payoffs; I don't think this is particularly uncommon. People lucky enough to have options in their career should be thinking long-term, not what is most immediately satisfying today.)