Shadowsan (Carmen Sandiego)

Shadowsan is a former member of the V.I.L.E. Faculty who became known as a traitor and defector upon his alliance with Carmen Sandiego being discovered. He is the one who saved Carmen as an infant and who brought her to V.I.L.E. Academy.
In V.I.L.E., Shadowsan was known for his discipline and no-nonsense demeanor, and was considered the strictest of the five Faculty members. He almost never cracked a smile, usually wearing a neutral, unfazed expression or a scowl.

He believes that origami is the best way to master the nimble touch required for pickpocketing, giving someone precision and focus, and improving one's attentiveness. He is extremely irritated by any lack of discipline, such as when 'Black Sheep' would pull pranks or disrupt class, or the times Paper Star would use her origami weapons in class for simple matters. However, Shadowsan couldn't bear to leave a young and defenseless infant Black Sheep in her father's burning home, proving that he has more morals than the other villains. While he failed to join Carmen during her escape from the Isle of VILE, he felt better afterwards, believing she'd start a new life until he had to contend with her stealing from V.I.L.E., complicating his position. In the months after her departure, he covertly 'reasoned' with the Faculty as to why certain operatives should handle some missions, allowing Carmen room for victory by helping select operatives whom Carmen could best. After defecting from V.I.L.E. and joining Carmen's crew, he retained his serious demeanor, often sternly quipping about Zack and Ivy's goofy behavior and being unfazed by their attempts to get him to lighten up. He and Player have a usually more cordial relationship, thanks to Player's assistance in providing intel and tech support to Team Red and his more serious demeanor about capers.

As a former member of the Faculty of V.I.L.E, Shadowsan had near supreme authority in the organization before his defection. He is a skilled origami craftsman, believing that origami is the best way to master a nimble touch necessary for picking pockets.
He knows the human body so well he can easily target its weak points, and can knock multiple people unconscious simply by pinching a specific nerve in their neck. He is highly agile despite being middle-aged.
As the former mentor of Stealth 101, he is a master at stealth, able to elude V.I.L.E's faculty and even Carmen herself. As a ninja, he has mastered the arts of hiding in plain sight and escaping enemy notice with ease.
Shadowsan is highly skilled with a sword, likely due to a need for swordsmanship skills being an assassin and close-quarters-combat specialist, and can cut through a metal padlock to break it. His weapon skills also extend to marksmanship, improvised weaponry such as chopsticks, and close quarters combat. He can handle most martial opposition from V.I.L.E with relative ease unless a trap or gimmick unbalances him. He has great reflexes, able to catch objects thrown at him even while he isn't looking.

Shadowsan is a middle aged Japanese man with a shaved head, a wrinkled face and a strong, physically fit and muscular body. His attire as a member of V.I.L.E.'s faculty included a blue-grey men's haori, accompanied by grey hakama and setta sandals. After joining Carmen's crew, he switches to a black polo with grey trousers and black shoes, as well as sunglasses. When he and Carmen engage in stealth operations, he wears a black shinobi outfit.