Hi OP! You might want to check the alcohol enema prompt fill on the previous page to get a taste of Matt/Wesley. It doesn't fill your prompt, exactly (it's just a scene), but it could fit it well.

About your prompt, though: does Wesley absolutely have to blackmail Matt? Or could Matt approach Wesley to get info on Fisk (and maybe Wesley knows that but lets him in close to play the same game).
Just workshopping ideas to see what could work.