Skull also infected the entire New York city with his Dust of Death, which might have possible killed many innocent civilians, just to discredit Avengers and kill Captain America, while being under the guise of "Dell Rusk", the secretary of US defense.
Red Skull from The Avengers: Earth's Mightiest Heroes crosses this in season 2 where we find out that he captured and brainwashed Bucky and turned him into Winter Soldier, an emotionless killing machine and made him commit several atrocities, and did the same to Doc Samson and The Falcon. In the Redhill story from Animated Tales of the World, the Adviser crosses this when he orders the guards to kill Nadine and his grandmother, even though he had already successfully convinced the Rajah that he shouldn't take advice from a young boy such as Nadine. Fittingly, at the end of the episode, he gets sent to jail (presumably for life) for his actions. Arthur: Supreme Dog crossed it in the only episode he appears in, "To Eat or Not to Eat", by distributing Big Boss Bars, which are explicitly said to contain radioactive ingredients, in Elwood City and marketing them specifically towards children, all so that he can make a profit. 
She bought him a bike for his birthday, then stole it and punished him for losing it, without even telling him what she'd done.
Malory crosses the Moral Event Horizon in Season 2 and 3 flashbacks to Sterling's childhood: she got him drunk and taught him to gamble so she could steal his Halloween candy, and berates him for being unable to hold his liquor. Major Jakov's Moral Event Horizon probably came in "Dial M For Mother", when he brainwashes Archer to turn him against Malory. Barry's Moral Event Horizon was probably murdering Jakov, another candidate for Archer's father. Even Archer himself feels bad about it, if it has any permanent damaging side effects. As of the second episode of the second season, Archer has implanted a faulty Russian mind control chip into the head of Len Trexler, head of ODIN and possibly his father. Despite Vi trying to reach out to her in parts 2 and 3, the way she looks at Jinx at the end of Act 3 shows she concedes that Ekko and Caitlyn were right and Jinx is far too gone. She tops off the ending by firing a rocket at the Piltover Council. 
Vi isn't willing to go through with murdering her new friend, and then through mishaps Jinx accidentally kills Silco who tells her that she is perfect the way she is, cementing her as being Jinx for good.
Arcane: Jinx crosses it when she kidnaps Vi and Caitlyn, and twistedly asks Vi to pick between killing Caitlyn or losing Powder as a sister.Walter Wolf, Slappy Squirrel's nemesis in Animaniacs, sinks to the ultimate low in "Rest In Pieces" by faking his own death in order to turn everyone against her, including her nephew!.Richard De Longpre from Allen Gregory crosses it when he stalks and blackmails Jeremy into leaving his family so he can become his personal Sex Slave.
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