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Personally, I'd say best character for thieving is a Bard. Yes, you can steal powerful items, just you have to be well skilled in Pick Pocketing. I think Stealth has something to do with it too. First off, you can click on the mask that you usually use to disarm traps and open locks, and put it over a character (merchant, ect.). That is one way of stealing. The other way is to talk to those who sell you goods, and click on the 'Steal' button. It looks like the ordinary 'Buy/Sell' screen, except there is no buy/sell. You choose the item you want, and click steal (or whatever the button is). Some items are in red, meaning you can't steal them or possibly you can't carry them.
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