So I know that when you take a guy to arb three times, he's gonna say he wants to test free agency and won't resign...

and I know sometimes that those players will change their mind after the league rolls over and will sign a new contract before free agency...

my question is, in those situations, how does their demands change? In this case, I had a player asking for the 15.8 max in arbitration, and he would have signed long-term at 9.75 million. In what was the worst mistake I will ever make in this game, he was not signed long term.

So if he decides next year that he will sign a new contract with me before he enters free agency - will his demands look closer to 15.8 million or 9.75?

He probably won't-- but if he does it'll be in the $9.75M range.

Patience rating? Right now I have a similar player who appears willing to re-sign and his Patience rating is 69. I've had players with Patience closer to 50 saying "Free agency no matter what." This player is a Type B so I'm going to let him walk. If your player is good enough to ask for max arb, he's probably a Type A and will demand around the 9.75, but he's worth more than that on the open market.