I think every NPC has a pickpocket difficulty associated with them, which is subracted from your pickpocketing score when you try to pickpocket them. Maybe his is really high? I could be wrong about this though. What's your pickpocket score?
When you're pickpocketing him, are you actually failing, causing him to go hostile and forcing you to reload? Because if you're simply not getting anything when you pickpocket him, that's because he has no items to pickpocket.
Yeah, there's a huge number of NPCs in this game who quite simply have nothing to pickpocket... they really should just rename the damned skill Shoplifting since that's about all it's useful for.
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