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SPOILER
Keep in mind what happens when a pickpocket is unsuccessful... If you take your character from BG1 into BG2 there will consequences down the line for harming Drizzt.
If you are roleplaying a good party then it would be evil to pickpocket him... Unless you feel you can justify placing your needs above whatever his may be (and there is no way to know if his need for his items is greater than yours)...
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