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* Aside from Clockwerk, [[AristocratsAreEvil Sir Raleigh]] is the only other sociopath among the Fiendish Five. While his co-horts each have a sympathetic FreudianExcuse, Raleigh was a spoiled rich kid who turned to a life of crime out of boredom. He treats his men like trash, gets a sadistic kick out of sinking ships and taking their cargo as trophies, and has a tendency to completely flip out at the drop of a hat. He's also okay with murdering children, and believes that the Five should have killed Sly as a kid when they had the chance.
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* ''Thieves in Time'' also gives us [[PsychopathicManchild Toothpick]], a [[AxCrazy violently insane]] armadillo working as one of Le Paradox's lieutenants. He's a terrible boss who treats his goons like slaves that he can overwork to his heart's content, and isn't phased in the slightest when he guns one down on accident. In fact, he threatens to kill another when he calls him out for his carelessness. Along with his itchy trigger finger and LackOfEmpathy, he's also ridiculously self-centered. Case in point: to get thrown into a maximum security prison to help his imprisoned ancestor, all Sly has to do is commit petty crimes that disrespect Toothpick, such as stealing his lollipop or tearing down decorations that pander to his ego.
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-->'''Neyla:''' Stupid Arpeggio. I double crossed the Cooper Gang, Interpol and Carmelita... what made you think I wouldn't do the same to you?
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-->'''Neyla:''' Stupid Arpeggio. I double crossed double-crossed the Cooper Gang, Interpol and Carmelita... what made you think I wouldn't do the same to you?
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-->'''Neyla:''' Stupid Arpeggio. I double-crossed Interpol, the Cooper Gang, and the Klaww Gang. What made you think I wouldn't do the same to you?
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-->'''Neyla:''' Stupid Arpeggio. I double-crossed Interpol, double crossed the Cooper Gang, Interpol and the Klaww Gang. What Carmelita... what made you think I wouldn't do the same to you?
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--->'''Neyla:''' Stupid Arpeggio. I double-crossed Interpol, the Cooper Gang, and the Klaww Gang. What made you think I wouldn't do the same to you?
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Panda King took up Meditation, not Medication.
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* [[PoliticallyIncorrectVillain General Tsao]], also of ''Honor Among Thieves''. He manipulates the Panda King into taking up medication to force his beloved daughter, Jing King, into marrying him despite her strong objections, all in the belief that marriage will strengthen their bloodlines. He cares only about family honor and is not above misogyny, animal abuse, and treating his guards like slaves because he doesn't believe in friendship. It's reached the point that even Sly admits Tsao is the worst of all the villains he faced.
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* [[PoliticallyIncorrectVillain General Tsao]], also of ''Honor Among Thieves''. He manipulates the Panda King into taking up medication meditation to force his beloved daughter, Jing King, into marrying him despite her strong objections, all in the belief that marriage will strengthen their bloodlines. He cares only about family honor and is not above misogyny, animal abuse, and treating his guards like slaves because he doesn't believe in friendship. It's reached the point that even Sly admits Tsao is the worst of all the villains he faced.
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* [[ArchEnemy Clockwerk]], the BigBad of ''VideoGame/SlyCooperAndTheThevievusRaccoonus''. A psychopathic owl and rival to Sly's family that was driven solely by his hatred for them. To that end, he turned himself into a {{Cyborg}} just so he could achieve {{Immortality}} for the express purpose of hunting down and killing each of Sly's ancestors, ending with his [[YouKilledMyFather father]]. Clockwerk's LackOfEmpathy is so great that he's not only incapable of feeling empathy, but he also [[EvilCannotComprehendGood views it as a weakness in others]].
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* [[ArchEnemy Clockwerk]], the BigBad of ''VideoGame/SlyCooperAndTheThevievusRaccoonus''.''VideoGame/SlyCooperAndTheThieviusRaccoonus''. A psychopathic owl and rival to Sly's family that was driven solely by his hatred for them. To that end, he turned himself into a {{Cyborg}} just so he could achieve {{Immortality}} for the express purpose of hunting down and killing each of Sly's ancestors, ending with his [[YouKilledMyFather father]]. Clockwerk's LackOfEmpathy is so great that he's not only incapable of feeling empathy, but he also [[EvilCannotComprehendGood views it as a weakness in others]].
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The Cooper Gang have sworn to only steal from villains and other criminals. It is no surprise that several of these villains [[TheSociopath have no sense of morality for anyone]].
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* [[ArchEnemy Clockwerk]], the BigBad of ''VideoGame/SlyCooperAndTheThevievusRaccoonus''. A psychopathic owl and rival to Sly's family that was driven solely by his hatred for them. To that end, he turned himself into a {{Cyborg}} just so he could achieve {{Immortality}} for the express purpose of hunting down and killing each of Sly's ancestors, ending with his [[YouKilledMyFather father]]. Clockwerk's LackOfEmpathy is so great that he's not only incapable of feeling empathy, but he also [[EvilCannotComprehendGood views it as a weakness in others]].
* [[ChronicBackstabbingDisorder Neyla]] of ''VideoGame/Sly2BandOfThieves''. At the outset of the game she was depicted as an Interpol cop with BlackAndGrayMorality who assists Sly and his gang, but after Ch.3 she reveals a glimpse of her true colors when she betrays the gang and has them arrested, even framing Carmelita as well. Her true colors are fully exposed during the finale where she is revealed to be working for Arpeggio, the leader of the Klaww Gang, during which she betrays him and steals the Clockwerk body for herself. Her response to Arpeggio's astonishment at her betrayal showcases her LackOfEmpathy.
--->'''Neyla:''' Stupid Arpeggio. I double-crossed Interpol, the Cooper Gang, and the Klaww Gang. What made you think I wouldn't do the same to you?
* [[MadScientist Dr. M]] of ''VideoGame/Sly3HonorAmongThieves''. He once served as the brains behind Sly's father's gang. Due to a Noodle Incident, he began to [[GreenEyedMonster feel marginalized out of his role of the gang]]. When Sly's father died, [[{{Greed}} he spent years attempting to open the Cooper Vault and claim the treasure inside for himself]]. Over the years, his greed made him paranoid and uncaring towards others, seen in his EstablishingCharacterMoment when he [[BadBoss poisons a guard]] for [[DisproportionateRetribution not changing the security code]] and coldly calling his assistant to clean up. His Lack of Empathy also extended to others as he nearly killed Sly and attacked Carmelita and her squad when she arrived to help. [[DeathByMaterialism His greed ultimately becomes his downfall when he refused to leave the Vault as it was collapsing]].
* [[PoliticallyIncorrectVillain General Tsao]], also of ''Honor Among Thieves''. He manipulates the Panda King into taking up medication to force his beloved daughter, Jing King, into marrying him despite her strong objections, all in the belief that marriage will strengthen their bloodlines. He cares only about family honor and is not above misogyny, animal abuse, and treating his guards like slaves because he doesn't believe in friendship. It's reached the point that even Sly admits Tsao is the worst of all the villains he faced.
* [[FrenchJerk Le Paradox]] of ''VideoGame/SlyCooperThievesInTime''. A criminal art smuggler and a descendant of a rival family of thieves who planned to use TimeTravel to make himself French royalty. Le Paradox displays all the traits of a classic narcissistic sociopath: [[LackOfEmpathy He feels no remorse for anything or anyone]], [[ManipulativeBastard he lies and manipulates others with a smile]] (even the woman he supposedly loved.), [[ItsAllAboutMe is selfish and driven by a staggering belief in his own superiority]], [[EvilIsPetty commits small acts of evil for ridiculous reasons despite it having nothing to do with his long-term goals.]], [[NeverMyFault and is quick to blame others despite clearly being in the wrong.]] His overblown ego is what ultimately leads to his downfall.
* [[EvilFormerFriend Penelope]] is revealed to be this in ''Thieves in Time''. [[ClassicVillain Embodying]] {{Greed}}, {{Pride}}, and [[GreenEyedMonster Envy]], her goal in life is to TakeOverTheWorld and make billions of dollars. She intends to make her fortune through [[WarForFunAndProfit weapon designs]], having no empathy for the millions of people who's lives she would likely ruin if she made deals with terrorists or rouge nations. Penelope doesn't even love her boyfriend Bentley at all, viewing him as nothing but a tool to her goals, and [[TrueCompanions his two best friends Sly and Murray]] as objects that [[RemovingTheRival must be destroyed]]. When Bentley confronts Penelope, he assumed she was merely a [[SlidingScale/{{Yandere}} Stage 5]] {{Yandere}}, but Penelope refuses to listen to him, gloats on how she'll use him for her selfish ambition, and then attacks him when he rejects her in disgust, proving to Bentley that [[ManipulativeBitch he's been played with]]. Even in her first appearance, as the Black Baron, she's a murderous SoreLoser who cheats at dogfight matches.
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* [[ArchEnemy Clockwerk]], the BigBad of ''VideoGame/SlyCooperAndTheThevievusRaccoonus''. A psychopathic owl and rival to Sly's family that was driven solely by his hatred for them. To that end, he turned himself into a {{Cyborg}} just so he could achieve {{Immortality}} for the express purpose of hunting down and killing each of Sly's ancestors, ending with his [[YouKilledMyFather father]]. Clockwerk's LackOfEmpathy is so great that he's not only incapable of feeling empathy, but he also [[EvilCannotComprehendGood views it as a weakness in others]].
* [[ChronicBackstabbingDisorder Neyla]] of ''VideoGame/Sly2BandOfThieves''. At the outset of the game she was depicted as an Interpol cop with BlackAndGrayMorality who assists Sly and his gang, but after Ch.3 she reveals a glimpse of her true colors when she betrays the gang and has them arrested, even framing Carmelita as well. Her true colors are fully exposed during the finale where she is revealed to be working for Arpeggio, the leader of the Klaww Gang, during which she betrays him and steals the Clockwerk body for herself. Her response to Arpeggio's astonishment at her betrayal showcases her LackOfEmpathy.
--->'''Neyla:''' Stupid Arpeggio. I double-crossed Interpol, the Cooper Gang, and the Klaww Gang. What made you think I wouldn't do the same to you?
* [[MadScientist Dr. M]] of ''VideoGame/Sly3HonorAmongThieves''. He once served as the brains behind Sly's father's gang. Due to a Noodle Incident, he began to [[GreenEyedMonster feel marginalized out of his role of the gang]]. When Sly's father died, [[{{Greed}} he spent years attempting to open the Cooper Vault and claim the treasure inside for himself]]. Over the years, his greed made him paranoid and uncaring towards others, seen in his EstablishingCharacterMoment when he [[BadBoss poisons a guard]] for [[DisproportionateRetribution not changing the security code]] and coldly calling his assistant to clean up. His Lack of Empathy also extended to others as he nearly killed Sly and attacked Carmelita and her squad when she arrived to help. [[DeathByMaterialism His greed ultimately becomes his downfall when he refused to leave the Vault as it was collapsing]].
* [[PoliticallyIncorrectVillain General Tsao]], also of ''Honor Among Thieves''. He manipulates the Panda King into taking up medication to force his beloved daughter, Jing King, into marrying him despite her strong objections, all in the belief that marriage will strengthen their bloodlines. He cares only about family honor and is not above misogyny, animal abuse, and treating his guards like slaves because he doesn't believe in friendship. It's reached the point that even Sly admits Tsao is the worst of all the villains he faced.
* [[FrenchJerk Le Paradox]] of ''VideoGame/SlyCooperThievesInTime''. A criminal art smuggler and a descendant of a rival family of thieves who planned to use TimeTravel to make himself French royalty. Le Paradox displays all the traits of a classic narcissistic sociopath: [[LackOfEmpathy He feels no remorse for anything or anyone]], [[ManipulativeBastard he lies and manipulates others with a smile]] (even the woman he supposedly loved.), [[ItsAllAboutMe is selfish and driven by a staggering belief in his own superiority]], [[EvilIsPetty commits small acts of evil for ridiculous reasons despite it having nothing to do with his long-term goals.]], [[NeverMyFault and is quick to blame others despite clearly being in the wrong.]] His overblown ego is what ultimately leads to his downfall.
* [[EvilFormerFriend Penelope]] is revealed to be this in ''Thieves in Time''. [[ClassicVillain Embodying]] {{Greed}}, {{Pride}}, and [[GreenEyedMonster Envy]], her goal in life is to TakeOverTheWorld and make billions of dollars. She intends to make her fortune through [[WarForFunAndProfit weapon designs]], having no empathy for the millions of people who's lives she would likely ruin if she made deals with terrorists or rouge nations. Penelope doesn't even love her boyfriend Bentley at all, viewing him as nothing but a tool to her goals, and [[TrueCompanions his two best friends Sly and Murray]] as objects that [[RemovingTheRival must be destroyed]]. When Bentley confronts Penelope, he assumed she was merely a [[SlidingScale/{{Yandere}} Stage 5]] {{Yandere}}, but Penelope refuses to listen to him, gloats on how she'll use him for her selfish ambition, and then attacks him when he rejects her in disgust, proving to Bentley that [[ManipulativeBitch he's been played with]]. Even in her first appearance, as the Black Baron, she's a murderous SoreLoser who cheats at dogfight matches.
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