I understand why they signed him. He only got 1 year, at a cheaper price than other teams would have paid, and if we take the Cup this year Holland looks great.
But it backfired because he just isn't good enough this season, even at that price. I think that's about it.
As Clearly himself explained (http://www.youtube.c...h?v=FggT39NPVG8), he actually wanted only a one year contract. Given that he also wants to be in Detroit longer, the only reason I can understand that he would take a shorter deal is that Detroit had a cap space crunch, but he believed he was worth more and that he could play well enough to earn more in his next contract.
I feel like it's similar to the situation in Ottawa, where Alfie took less money and then felt slighted when he wasn't given more to compensate in his next contract. I think Cleary has taken less with the impression that Detroit would "take care of him" with a bigger and/or longer contract afterwards.
Given the shape he's in though, it's hard to see if they could justify giving him another contract let alone a raise. That said, depending on other signings Detroit may have more roster room than they had this past year, when they had no space and still signed Cleary. Because of this I honestly think we will see him re-signed.
As Holland said at training camp "at some point and time as the season wears on or next summer, we'll try to find a way to keep him in a Red Wing uniform for longer than a year." http://www.youtube.c...h?v=mG6LST7PPLc
I can't see any other team offering him the kind of money that Philly apparently was going to, and so if Detroit does offer him a contract, I hope they come to terms on 1-year at about 1 million. At that rate, it's a low risk deal and I don't mind Cleary as a depth player as long as he's not taking a roster spot from someone who is already under contract.