The main boards video with the spliced together interview clips is telling. He gives a canned answer over and over. He never truly commits to anything and clearly leaves the door open to leave. "I love it here and hope it works out" is not the same thing as "I'll sign a contract for $11 mil per". If NYI management chose to believe him in all this it's on them in my view. That said, JT should have been more candid with them. Tell them you want to see what else is out there and that you won't close the door on NYI but aren't sure what makes sense for your future. That's responsible and at that point NYI have to either trade him or hope for the best in an honest atmosphere. What he did strikes me as disingenuous. I don't think he knew he was leaving, but I think he knew he wasn't signing before July 1 specifically because he wanted to see what his options were.
Applying this to Hall, the signals are different. Sure, Hall gives general answers, but his agent has specifically said he doesn't foresee any problems with re-signing Hall. Given the timing with the year remaining, I'd expect it to get done. If the agent made general statements or had no comment I'd say it might be tougher. Sure, the agent could be blowing smoke, but right now, the team holds the cards for the upcoming season.