Pickpocketing

Pickpocketing was an important method of gaining information, money, or items, and was a tactic that was often employed by thieves and members of the Assassin Order.

High Middle Ages
For Assassins during the Third Crusade, pickpocketing was used for gathering letters or other items from informants, as well as for restocking on throwing knives. Oddly, targets for pickpocketing would always carry satchels on their left sides.

To pickpocket an informant, usually after eavesdropping on them and discovering what they had in their possession, Altaïr Ibn-La'Ahad approached the target quietly from behind, before reaching out to slip the desired item from their satchel. Should he not move away from the target after they discovered the theft, the victim would often call the guards to attack him.

Optimally, pickpocketing targets was only viable if they were moving, not facing the one targeting them, and if they were positioned far from a guard. This method was also the only way for Altaïr to gather throwing knives, apart from returning to Masyaf or visiting an Assassins' Bureau.

To do this, Altaïr would acquire knives from certain thugs, who – unlike regular citizens – would engage Altaïr in a fistfight if they discovered his attempt to steal from them. Should they be nearby, other thugs would also join in and assist the target.

Each thug carried around five knives, all of which could be stolen. However, upon being discovered and defeating them in a brawl, Altaïr would only be able to take one knife from the beaten thug.

Renaissance
Ezio Auditore da Firenze learned how to pickpocket from a fellow Assassin, Paola, soon after the execution of his father and brothers. Pickpocketing was an optional way to acquire florins, as well as items.

Unlike Altaïr, Ezio would only pickpocket money from civilians. However, he also looted both money and items (usually trade items or ammunition) from dead or unconscious guards. Doing so in public, though, would usually prompt nearby citizens to reprimand him.

Civilians – both male and female – who discovered Ezio's efforts, would engage him in a fight and would usually flee after a single strike.

Ottoman Empire
The Turkish Assassins created the hookblade, which came in useful during conflicts to perform a counter-steal: an Assassin could simply rip a purse off a guard, enraging them.

American Colonies
The Colonial Assassins could pickpocket both civilians and guards to steal a variety of items or to simply take their money. The Assassin would stand next to their target and search their pockets or pouches for items. Searching for a longer time yielded more money and items, but the target and all nearby guards would get suspicious of them.

Pickpockets
Like Borgia Messengers, several thieves roamed the streets and rooftops, and would often seek out Ezio to steal from him. One such pickpocket was successfully able to take his money in Florence, though the thief had only intended to lead him to La Volpe.

As well as this, pickpockets would only approach Ezio if he was not looking at them, and would flee immediately should he notice them. If pickpockets took his money, Ezio could chase after them – with the help of any nearby guards – and tackle or grab them to reclaim his money, as well as taking the money the pickpocket had obtained from other marks.

Alternatively, should Ezio or a guard kill the pickpocket, the Assassin could simply loot the body to take back his money.

Trivia

 * Unlike in other instances, pickpocketing in Assassin's Creed: Altaïr's Chronicles both involved approaching the target and maneuvering the desired item out of their item pouch.
 * In Assassin's Creed II, the pickpocket would always steal 5% of Ezio's total florins.
 * In Assassin's Creed II, Assassin's Creed: Brotherhood and Assassin's Creed: Revelations, after bribing a herald, the money could be stolen back from him. Alternatively, the herald could be killed and the corpse looted to re-obtain the money.
 * After completing five Thieves Guild challenges, hired thieves would pickpocket money for Ezio.
 * As well as this, thieves in Constantinople could loot the bodies of dead guards for Ezio, once he had completed a specific challenge set.
 * Certain guards held more florins than others when looted, with certain Borgia Captains carrying more than 900 florins. Also when Ezio journeyed to the city of Constantinople, the Janissaries could be looted for up to 84 akce,
 * Ezio could also perform a counter-steal during combat to snatch the satchel of the Janissary, in order to obtain their akce.
 * Naturally, civilians in richer clothing carried more florins.
 * Like Borgia messengers, pickpockets in Assassin's Creed II would drop their florins if they were struck with a throwing knife.
 * The Easy Come, Easy Go achievement/trophy has been known to be glitched and not trigger.