03 Mar 2014 03 Mar 2014
There are two ways to this acheivement
Stealth or Force
Use focus to see if the target got a pouch (its around their waist). sneak close to them and hold X to pick pocket them.
Use your blackjack and force them into kneeling, usally you would just finish them off by holding X but instead be fast and go around their back and hold X to pick their pockets before they stand up again, when you have taken all their loot then finish them off.
This can be done on guards in the city and on any chapter or job. Even after you complete the game you can still go for the acheivment.