Objectively, it's using nukes in Civilization and the Alpha Centauri game. In AP it's even worse cause you can sink parts of the maps and create more ocean within the blast radius if I remember correctly.
On a more personal level, Spec Ops: The Line (Spoilers for the game to follow). One of the endings has the MC go crazy after finding a certain revelation in the plot. After an unspecified amount of time passes, he's found by a group of American soldiers and he looks very disheveled and wearing the uniform of a dead man. You can choose to surrender your weapon and go with the soldiers or go full insane and kill 'em all. I admit that I wanted to see the ending (and the trophy) so I went for the insane route.
Felt super dirty afterwards. I think I remember reading that the developers didn't want you to get trophies by choosing certain moral decisions so it might have been a decision by the suits. Regardless, the whole thing taught me a valuable lesson: some trophies aren't worth getting.
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