Why? It sounds more realistic for him to be the only person with his point of view who had evaded prison. Finding everyone who ever agrees with him ending up in prison puts across the moral issue fairly clearly.
That's HIS problem, not yours.
I have seen too many bad players who insist that realistic consequences are only proof the GM is being a "meany" -- which is their favorite trick for trying to guilt-trip or browbeat the GM into letting them realign realism itself for their own personal convenience.
To be completely honest with you, it sounds to me as though your player had mastered the arts of browbeating, bullying, guilt-tripping, and whining as necessary to control you like a puppeteer pulling the strings of his favorite wooden marionette.
To put it more colloquially: he been playin' you the whole time.
I would never allow any player to try to bully his way through a game by using phrases like "The DM is a twit!" I would politely tell any player who tried such manipulative tricks on me that he was free to play elsewhere; if he continued, I would refuse to game master him any further until he grew up. No Game is always better than a Bad Game.
It sounds to me as though you enjoyed the challenge of running your game under his rules, though. If you both had fun, it doesn't matter what I write or anyone else writes, really.
P.S. Look up the studies on macchiavellianism as a personality trait or condition, and you'll probably nod at how often the descriptors fit him.






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