Well the true deadline isn't until his contract expires and before he signs elsewhere. Nothing wrong with him trying to get all he can and perhaps all this talk about wanting to stay a Blue Jay for life is just posturing. If his asking price is a contract that begins with the number 5 (and I suspect it does) then we all know what the prudent course of action should be: Trade him while you can.
Yeah, the usual suspects will blame this on Jays management not being able to close a deal with their franchise player but at some point common sense has to prevail, right?
I've always been in the sign Vladdy camp but looking at the situation from a purely analytical perspective, in a few short years he will be on the wrong side of 30, do you really want to empty your pocket book for what could be Prince Fielder 2.0 at that point?