I'd rather the Hellfire club be more ambiguous than straight-up evil. I imagine Angel going in there, using the Worthington name and fortune, at the same time Black Tom Cassidy does and it would be a title all about these shades-of-gray characters falling on one side or the other.
Here's my roster...
White King: Warren Worthington because he inherited membership from his family. Maybe it would be Angel's way of reforming the Hellfire Club from the inside or, better yet, he's just conflicted.
White Queen: Madame Masque she's prominent in the Maggia crime syndicate so she's powerful but she's also a sympathetic character in a lot of ways too.
White Rook: Moonstone I liked Moonstone's involvement in the Dark Avengers, she came off as intelligent and effective but almost sociopathic, she'd create some interesting controversy.
Black King: Black Tom Cassidy is a good idea, I agree with @knighthood
Black Queen: MONET would be perfect because she's powerful in might and in influence. She also is a nice contrast to Emma whom she has a history with.
Black Rook: Hood, he has run syndicates before and he also can alter reality. He's involved with Madame Masque so that could provide for some interesting dynamics.
Black Bishop:Mystique because she's a brilliant criminal mastermind and tactician and she works much better as an anti-heroine than a cartoon villain like they've made her. Making her a teacher at Hellfire Academy was so ridiculous...she needs to be running the place, not begging for tenure.
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