My First rounder hasn't signed, and keep getting that he is content with the offer, but college is still an option.

We are now at game 162. Is there any chance he signs at this point? I've never had it drag out this long before.

There's no deadline that I'm aware of, so it's possible for him to sign at any point up until rollover.

It sounds like you may be re-making the offer after he says he might want to go to college. Don't do that; it resets the clock to zero. Just wait for him to follow up after he gives you the "college is still an option" response.

Great, thanks. I will wait and see what he does. Yea, I was periodically re-offering to see if i could get an answer from him. (usually when there was an IFA i need the his money for).

Sounds like you never gave him time to make a counter. He may never have done so, but since you kept pulling it and then re-offering, he never got to that point.

Good news is there is still time. If you stop playing around and just leave the offer he will come back with either "sorry, but I am going to college". or "I've decided I may want to sign, however I have raised my demands a small fraction".