If you said I'm putting the wrong theme over the art, actually it fits the art very well. In my headcanon, Grimsley is somewhat like Flandre, an eccentric lad (while still keeping the facade of an educated upper-class man). He keep turning your money into ashes by keep luring you into bets that consuming your money like a guzzler. You are not able to get out of his never-ending cycle of bets and losing money due to losing his bets unless he is kept in control by the other Elite Four members, especially Marshal, who will give him a head drill whenever he do something that is too risky to others around him (such as him placing bets and have others lose those bets, "burning" their money like guzzlers).

Also, like Flan (Flandre), he has made very few appearances in the whole franchise (except his appearance in SM in which he is given a new appearance; and he even didn't appear in the Pokemon anime at all (but Flan has appeared in many fanmade Touhou anime)), and he is a vampire in disguise (?) (at least in the theories of some crazy game theorists, but I don't think so, he just dress like that because he thinks it's cool). Despite he does not receive the same level of popularity as Flan did, he is surely amazing and dashing to look at (and he is a girl-magnet, in my opinion) (and similar to Flan's "cute" appearance despite she is a vampire).

Why Mari's knives are here? I must admit that this is a minor meme (and fanfic) I created: Grimsley went into Gensokyo after Yukari spiriting him away while in the middle of a break between poker matches. There he met Mari, who taught him about the power of the Cross and how to harness its power by exercising faith in Christ. Mari also taught him how to use the throwing knives she uses in case of him becoming an incident-solver like her (despite that Unova never have any serious incident involving youkai / gods, and currently none of its residents ever go pew-pew, chucking throwing weapons in their adventures), and gave him a replica set of throwing knives similar to hers. Back in Unova, he became an expert in throwing knives at apples with outstanding accuracy, while becoming a devout Christian.

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