Checker

Checker is Arthur's business partner and friend, and happens to be an elite hacker. He isn't malicious, and at one point he identifies himself as an "overzealous white hat [dude] who [is] creative enough to step out of the narrowly confined boxes proscribed by our myopic legal system." He is a thin Caucasian man with a past the led to him being in a wheelchair, although he doesn't let that slow him down. He flirts with just about every woman he meets, including Cas and Pilar, but is respectful of boundaries and doesn't hesitate to call Cas out on gender slurs. He becomes one of Cas's friends, drinking with her, backing her up, and pushing her limits on learning what friendship means. We don't know his past yet, but we get some hints in Root of Unity (yet to be republished).

Image:

Ivan David Gomez Arce, CC BY 2.0