I continue to see multiple contradictions. You say it was not an unfun game session but you’re sad after the fact. You express disappointment with the player’s choice - that they had no consideration, and they were being a kleptomaniac - again not in a positive light, but in a disapproving way. You are sitting in judgment of the player’s choice, like someone who’s partner just misplayed a hand of bridge and is not happy with them. This does not come across to me as a game where the rogue character pushed his luck and got himself killed and everyone’s happily telling the story later about how the scrawny thief tried to make off with a 200 pound chest of treasure. That would indicate everyone had fun. Your story, as presented, doesn’t.