If he gets executed for doing a jailbreak (we all know he'd get caught), then the party you want him to put before all else will be much worse off than if he "slacked off" a little in a *prison cell*.
Yeesh, there's a line between tough love and just being unreasonable. Don't ask him to become a criminal, ruining his goal to change himself, just for the sake of your own arrogant goal of #1 mage.