I'd rather try and win a title. We're killing our chances next year to obtain two young players, neither of which are projected to be franchise players. Will either of them see an all-star game before PP retires?
For me, it would depend on a few things. First, what is the filler? If its something like Ridnour and Milicic, then I would consider it, since they both would bring important depth, and would allow the C's to trade Green for someone like Chris Kaman, and then let them use the MLE on someone like Crawford or maybe JR Smith.
That would actually help to balance out the C's roster pretty well (assuming, as I am, that Williams can step right in, and be a solid role player off the bench), while also giving them some nice building blocks going forward.
But I just don't think it works as well for Minnesota.