The Cooper Gang have sworn to only steal from villains and other criminals. It is no surprise that several of these villains have no sense of morality for anyone.
- Clockwerk, the Big Bad of Sly Cooper and the Thievius Raccoonus. 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 father. Clockwerk's Lack of Empathy is so great that he's not only incapable of feeling empathy, but he also views it as a weakness in others.
- Aside from Clockwerk, Sir Raleigh is the only other sociopath among the Fiendish Five. While his co-horts each have a sympathetic Freudian Excuse, 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.
- Neyla of Sly 2: Band of Thieves. At the outset of the game she was depicted as an Interpol cop with Black-and-Gray Morality 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 Lack of Empathy.Neyla: Stupid Arpeggio. I double-crossed the Cooper Gang, Interpol and Carmelita... what made you think I wouldn't do the same to you?
- Dr. M of Sly 3: Honor Among Thieves. He once served as the brains behind Sly's father's gang. Due to a Noodle Incident, he began to feel marginalized out of his role of the gang. When Sly's father died, 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 Establishing Character Moment when he poisons a guard for 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. His greed ultimately becomes his downfall when he refused to leave the Vault as it was collapsing.
- General Tsao, also of Honor Among Thieves. He manipulates the Panda King into taking up 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.
- Le Paradox of Sly Cooper: Thieves in Time. A criminal art smuggler and a descendant of a rival family of thieves who planned to use Time Travel to make himself French royalty. Le Paradox displays all the traits of a classic narcissistic sociopath: He feels no remorse for anything or anyone, he lies and manipulates others with a smile (even the woman he supposedly loved.), is selfish and driven by a staggering belief in his own superiority, commits small acts of evil for ridiculous reasons despite it having nothing to do with his long-term goals., and is quick to blame others despite clearly being in the wrong. His overblown ego is what ultimately leads to his downfall.
- Penelope is revealed to be this in Thieves in Time. Embodying Greed, Pride, and Envy, her goal in life is to Take Over the World and make billions of dollars. She intends to make her fortune through 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 his two best friends Sly and Murray as objects that must be destroyed. When Bentley confronts Penelope, he assumed she was merely a 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 he's been played with. Even in her first appearance, as the Black Baron, she's a murderous Sore Loser who cheats at dogfight matches.
- Thieves in Time also gives us Toothpick, a 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 Lack of Empathy, 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.
