So in Skyrim you can pickpocket people. However as the value of the item increases the success chance reduces. This is dependent upon skills and perks. The formula practically caps at 2100 or so, but the minimum chance of 1% caps at like 3500 or so. There is a trick around this.

You can sneak a potion of paralysis into someone's inventory and they will drink it. This allows for you to be able to succeed no matter the value of the item. I have decided to dub this method the: "Cosby Method".