I get that, sure - but, as I've said before, if I'm Jimmy, I want to get into a situation where the job is mine to lose (and with some guaranteed money), not one where they're waiting for me to die to begin their sunshine years.
And I said "flailing" because there is nothing good for SF coming out of that statement. I've already seen the national/Boston writers jumping all over it with comments like: there goes Jimmy's trade value. KS is essentially devaluing one of his assets and very possibly causing hard feelings.
I don't see things as cut and dried "how much are you paying me?" situations. My guess with Jimmy is that he could land a pretty good deal right now. The down side is a fall off the cliff, Trubisky style (if he gets benched for a kid), the upside minimal. Comments like this also reinforce the impatience of the fans he'll be playing before.
There was no reason for KS to phrase it the way he did.