He's looking for a 3 year deal. And reportedly, Milwaukee and the Cubs are the two teams interested. Based on geography, it seems pretty apparent that Dempster wants to return to the shores of old Lake Michigan ASAP.
Personally, I say why not. It's not as though adding Ryan Dempster at, say, 3 years / $30-35 MM is going to hurt our cause moving forward - he's old enough that it's not likely he's going to fall off the table at this point, and as we just demonstrated, the guy CAN be traded as the contract wears on.
More importantly, we're going to need 5 above-average-to-great guys in the starting rotation when the Rizzo-Castro core hits its stride, and at the moment, it takes some wishing and hoping to get us to 5 guys who can fill that role. Even if 2015 Dempster is a #5 making $10 million, well, someone has to be that guy. It may as well be someone who really wants to be here.