PokéBase - Pokémon Q&A
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Can I have a Pokemon use thief to obtain an item from a trainer (npc) battle and then defeat that Pokemon and then battle that trainer to thief that same item again and have more than one of that item?

I apologize for the long drawn out question.
-Charizard

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Thief will steal an item from an NPC permanently in Gens 2-4, but thief will not be permanent in Gen 5. So if you battle somebody that has a Pokemon with a held item, you could thief that held item, and then that person would have the item back, so you could thief it again.

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It works as long as the Pokemon using thief has the item it holds in the moment is taken away after battle.

Source:experience

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i'm sorry but this answer isn't very clear
I`ll edit it.
If it isn`t clear still, then I`ll hide it. `Cause that is as clear as I can get.
yeah its ok i guess
I understand your answer and will give you an upvote. Heracross gets the BA because it explains more, not more clearly.
It`s fine by me.(: