Rules FAQ
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Howland will reduce the cost of events as well.
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If Howland enters play after you have already brought a card out of shadows that round, he will "remember" that and not reduce the cost of the next one.
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If you bring a card out of shadows without paying its shadow cost (for instance, Smallfolk Mob), it will count as the first card you bring out of shadows and "waste" Howland's cost reduction.