Look, I know I cannot stop talking about Shadowsan and I’m two steps away from changing my icon to a picture of him, but I just need to say this-
Shadowsan and Carmen’s relationship is so deeply important, not only due to the familial bonds they found in each other over season 2, but how they have influenced each other from the very moment Shadowsan met Carmen.
Shadowsan is shown to have been young and reckless, and while he does not see himself as truly “evil”, the regrets of his actions are carried with him throughout his life. The moment he took that sword and went his separate ways from his brother, he saw no way to ever go back. Every choice he made from that point on sent him deeper and deeper.
During his time with V.I.L.E., he saw himself as nothing more than a soldier who must carry out the orders given to him. By the time he was sent after Wolfe with the mission to kill if necessary, any hope of redemption was lost. He could never escape V.I.L.E. no more than he could escape the crushing regret of the choices he made with his brother.
And then there was Carmen, the little Black Sheep he brought back to V.I.L.E. because he couldn’t stand to “wipe” her existence along with Wolfe’s. Black Sheep, who despite growing up around people who genuinely believed themselves to be evil and reveled in it, had kind & strong heart. Black Sheep who day after day forged her own path and made her own choices and rebelled against V.I.L.E. while Shadowsan hadn’t been able to even fathom such a thing...
Shadowsan wasn’t able to escape with her during her first attempt, and he was content with that because she finally had the choice, the freedom, that was so out of his grasp.
Carmen’s not just his adopted daughter, nor is she just his “teacher” as he claimed in the first episode of season 2. Carmen was proof, living and breathing evidence that he could escape and be more than he had let himself become.
Shadowsan didn’t join Carmen because he thought she needed his help. Shadowsan joined Carmen Sandiego because he needed her.