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Such an evil bastard Kodai is...
- Charon from Pokémon: Diamond and Pearl Adventure! accomplishes this before he even shows up, by ordering some of his mooks to suicide bomb the Pokémon League tournament.
- In Pokémon Adventures, Ghetsis was already on the line due to having raised his own son N to be brainwashed against humanity all so that he could be a puppet in his Evil Plan, but his moment officially comes after Black has defeated N. He admits to having never loved his "warped, defective freak" of a son (he has a pleasant smile on his face as he says this), then tries to have Black silenced by sicking a team of Pokémon specially trained to counter Black's team so that he's left defenseless and able to be killed on him, indicates he'll have all of Black's Pokémon killed as well, and then after he's lost, uses his associate's Pokémon to ensure that Black gets sealed inside the Light Stone while he makes his escape, mocking him as he does so! This cemented Ghetsis' status as perhaps the vilest villain of the series to date.
- The point where Kodai from Pokémon: Zoroark: Master of Illusions really crosses this may vary from person to person. However, the most likely is when he freaking electrocutes a baby right in front of its mother. Unlike the other horrific things he did, this is really the first time he's shown doing something terrible that didn't have anything to do with his plan, as Zoroark stopped attacking the moment she saw he had Zorua. He even comes right out and says he enjoyed it directly after that. He probably didn't know at the time that absorbing the Time Ripple would wither the plant life of Crown City completely, but he sure doesn't give one fuck if it happens again. Furthermore, he MURDERS ZOROARK IN FRONT OF HER SON (she got better) and choked out Celebi! That said, his Humiliation Conga was extremely cathartic.
- Cyrus from the Diamond and Pearl arc of the Pokémon anime crosses this line when he orders Mars to blow up Iron Island, which is full of Pokémon and people living there - sporting a Slasher Smile whilst giving that order.
- Pokémon Hunter J, in the "Pokémon Ranger and the Kidnapped Riolu" two-parter, really shows her cruelty when she tries to kill Ash (a 10-year-old boy) several times. First she orders her Salamence to burn the surrounding forest and fire Hyper Beam directly at him, then has her Drapion squeeze him tightly, and finally ejects him from her ship at great height. She also says that she wanted to punish Ash personally and took pleasure in trying to kill him and everytime she attacks Ash she is shown with a Slasher Smile.
- Damian, the former trainer of Ash's Charmander, crossed it when he refused to come back to Charmander (simply because he considered it to be weak) when it began to rain and Brock told him that rain would make Charmander's tail flame go out and it would die. He crosses it even further when it's revealed he couldn't care less about putting in the effort of training Charmander himself, outright saying that raising a Pokémon is a boring waste of time.
- Lord Ghetsis of Team Plasma in the Episode N arc crossed the line when he ordered a mind-controlled Reshiram to incinerate everyone currently at the White Ruins...which included several members of his own team! Team Rocket even calls this out as being self-centered and deplorable.
- If Lysandre's capture of the Zygarde core in the Team Flare Crisis arc doesn't do it, then he crosses it shortly thereafter when he lays waste to Lumiose City and captures Ash and his Pokémon for information on the Bond Phenomenon. Alain, who is normally The Stoic; is left horrified that he willingly helped Lysandre accomplish all this.
- Viren from Sun and Moon proves himself to be an irredeemable scumbag when he orders his Electivire to launch a Thunder attack on Mimo, Kiawe's little sister, for protesting against turning their family's ranch into a resort hotel. Turtonator blocked the attack and was KNOCKED OUT.note If it could KO a Pokémon that's resistant to Electric-type attacks, imagine what kind of damage it could have done to a frail, little human girl.
- Guzma entering the Alola League with the intent of destroying the legacy of Professor Kukui before it even starts is seen as this In-Universe, and is shown with his battling style: he has his Scizor deliberately attack the mother side Mega Kanghaskhan so her child can't fight back, solely because Ilima was favored to win. His battle with Lana then has his Golisopod use Throat Chop on her Primarina so she can't use song-based attacks, leading to a major Curb-Stomp Battle. Then it gets subverted when his Scizor loses to Ash's Torracat as a result of what happened with Ilima, then further when Guzma accepts his loss to Ash and decides to better himself as a Trainer.
- Cyrus from Pokémon Diamond and Pearl, whose plan was literally to control the powers of time/space and use them to wipe out the entire universe and all life in it so that he could then become a deity and recreate reality as he saw fit, which would be a reality without spirit, meaning all living creatures would now exist with no emotions, free thought, or free will. Granted he believed this to be in humanity's best interest, but it's still a sick and horrifying goal that he wanted to force on others. The lengths he took in the name of this goal were not pretty either, especially his plan with the Galactic Bomb and the torture of the three lake Pokémon in order to create the Red Chain.
- Mad Scientist Charon, who was in charge of making the Red Chain, shares in that last one. And he had his own terrible plan to use Heatran's destructive powers to terrorize entire civilizations in order to extort money from them that thankfully never took off thanks to the player character's interference. His true crossing might be in backstory details, since his journals suggest that he had discovered and befriended Rotom when he was a child, but when he grew older, more greedy and cynical, he used Rotom for little more than research and experiments, ultimately discarding it once he was done. In the present day, Charon thinks of nothing but himself and his own gain of money, power, and status.
- Pokémon Black and White: Ghetsis, Ghetsis, Ghetsis... You neglected your own boy, left him among abused Pokémon to ruin his perception of the world, raised him to believe Pokémon should be separated from humans, and gave him control over a group that only knew of his ideal. But that you'd abandon your kid after his failure to perform, call him a blasphemy upon mankind for the very way you raised him, and go against everything you ever taught him just for self-profit? Yeah... you can rot in jail for the rest of your life.
- Black 2/White 2 reveal that N is not even Ghetsis' biological son. He's just some orphan/runaway that Ghetsis found one day and decided might be useful to him in some way.
- In Black 2/White 2, it got worse. He has Kyurem in his possession, has it placed inside a machine and tortured so that it's power can be channeled through the Plasma freeze canon, which Team Plasma uses to freeze over half of Unova. Ghetsis' plan is to threaten to freeze the entire region in order to extort power and control from the masses terrified for their lives and health. To keep Kyruem in line and make it comply with Team Plasma's acts of terrorism, he physically and mentally tortures it with the Mind Control technology in his cane. When he takes Kyruem to the Giant Chasm in order to boost it's power, the player character interferes. So what does Ghetsis decide to do? Order Kyurem to attack the Kid Hero directly with a Glaciate attack, intending to freeze him/her alive or to death. So not only is he showing he Would Hurt a Child, but he's not even bothering to follow the conduct of Pokémon battles, preferring to have his super-powered monster lay a direct fatal attack on the kid! And he hopes that he/she will die in a state of despair and hopelessness, knowing that they've failed and he has won. This above all shows that Ghetsis is a sadistic freak of nature.
- Ultra Sun/Ultra Moon expands upon Ghetsis' horizon-crossing moments despite him not being the same one as the one from the main timeline due to him being pulled from a dimension where he ACTUALLY succeeded in banning all Pokémon. Here, he, out of his usual refusal to accept defeat, actually strikes Lillie onto the floor and threatens to kill her unless the Player Character surrenders to him, which is made worse by the fact that he's willing to kill a child with his own hands due to all of his Pokémon having been knocked out beforehand. Thank goodness Colress shows up in time to save the day.
- In Ultra Sun and Ultra Moon, Lysandre has the ultimate weapon constructed within Aether Paradise and threatens to use it to annihilate everyone unless you defeat him in battle, following a Sadistic Choice that makes you activate it.
- Faba, a Child Hater and Smug Snake in his own right, soars across the line in Ultra Sun and Ultra Moon when he sells out the Aether Foundation to join Team Rainbow Rocket just because he wanted to further his own career.
- Then there's Purple Eyes from Pokémon Ranger Guardian Signs. Before we even learn he exists, he's beaten Rand within an inch of his life and kidnapped both his wife and daughter. Later, he beats the daughter up, too! He kept getting worse up until he thought it would be a good idea to bark orders at Arceus—at which point he dearly paid for it.
- From Pokémon Mystery Dungeon: Explorers: Darkrai has a few opportunities, the earliest being orchestrating the planet's paralysis, making the future a frozen, endless night, with insane Pokémon and which is ruled by Primal Dialga, and the one way to stop the paralysis would cause all life from the future to disappear... which happens to include the player. Though Explorers of Sky shows that the good future was saved and everyone including Grovyle and Dusknoir survived. Though it was never truly explained why, aside from a vague implication that Arceus spared them.
- In Detective Pikachu, if Roger Clifford didn't cross it by being responsible for Harry Goodman's disappearance and presumed death prior two months prior to the events of the game, then wanting to send the Pokémon Carnival into chaos by poisoning the Pokémon in Ryme City with R and trying to kill Tim Goodman in the final chapter of the game pushes past the point of no return.