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They did an absolutely Excellent job at simply ignorong questions like these, so from what I know we have no official say to what happens Iron Will VS Iron Will
I wouldn’t read too much into that. One of this expansion’s big selling points is making villains available as Friends. Not just antagonists; big names like Nightmare Moon and Queen Chrysalis. Plus, there are already two Problem cards revolving around the damage Iron Will’s “motivation” did. At least now he can help fix what he started.