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Originally Posted by vaughnerich
1. "Little Dude." A player was wearing two headgear items due to "Cheat" card. Then the "Little Dude" curse was played on him. So do both of his hats attack him or just one? The card references "it" because you typically would only be wearing one headgear item.
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Curse! Little Dude says that you lose the Headgear you are wearing, so you will lose Headgear even if you're using Cheat! I would say you only have to Run Away once, but I'll see if I can't poke Andrew Wolf (the designer from USAopoly) to get a confirmation on how they want to handle it.
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2. "Cheat" Player is wearing two hats because of "Cheat" card. One of these hats is class dependent. Then a card is played that makes him have to change character and class with another player, so the cheat item no longer is in line with his class. Can he still wear it as a cheat while already wearing it to negate the "only one headgear" rule? Or would he have to pick one rule to break only?
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Cheat! covers any and all reasons that an Item might be "illegal," so it doesn't matter what the original reason may have been. The easiest way to think of it is as long as the Item has
Cheat! attached to it, that Item is legal for you to carry and use. Trying to remember why it was originally illegal and the Cheat! card was needed makes for too much bookkeeping.