Has anyone out there been able to pickpocket the "Dean Of History" at The Bards College? I cannot, even with the pickpocket skill at 100, a potion and being muffled and invisible. I was able to rob Faralda finally, while she slept.

Pick-pocketing someone is always a 100% success if you Paralyze them, and pick-pocket them while they're getting up from it.
with that method, if you can see the Item in their inventory, you can get it that way.

I can't believe I hadn't tried that. I have tried paralyzing them, but not while they are getting up. Thanks. I am traveling to Solitude now! This is the only place a person can ask such a question without looking like a total nerd!