I don't think any of us have any idea why he was confined to the jail. But, he was and unless he makes a deal with Matt and-or convinces the rest of us to plead his case to Matt, then here he is likely stuck.
The key to the ball-and-chain is in his hands, but he has to be willing to put it in the lock and turn it.
As for lightening up, he has given us no reason to do so. It really does not take much to convince most of us (a lot less than it takes to convince Matt most of the time), but it does take something.
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