In 2012's "Revelations", J.R. to an unconscious and critically ill Bobby:
J.R.: Come on, wake up, you hear me? Wake up and you get better. And you keep fighting. You keep fighting me! Now I'm gonna tell you something you never heard me say before: I love you Bobby, and I don't know who I'd be without you.
Bobby breaking down and crying after J.R.'s funeral.
Just J.R.'s funeral in general.
Pambecca miscarrying her twins. Cliff's move of ordering the explosion on the rig, even after finding out she was on there, definitely means he's crossed the Moral Event Horizon