Pickpocket

Pickpocketing is the ability to pick coins, loot and any other important items from a guard's pocket. It serves as a default ability in each game, with the exception of Sly Cooper and the Thievius Raccoonus. In Sly 2: Band of Thieves, Sly Cooper is the only character who can pickpocket, using his cane to do so. In Sly 3: Honor Among Thieves, Bentley and Murray also get the ability to pickpocket, though not in the same way that Sly pickpockets. In Sly Cooper: Thieves in Time, Sly, Bentley and Murray still retain this ability, however, it has also been given to each of Sly's ancestors.

To pickpocket, the character must remain unseen whilst sneaking in range of the guard. The actual method of pickpocketing varies between the users.

Sly and the ancestors
To pickpocket, Sly needs to get near the guard's pocket and press to swipe something out. While behind a guard with something in their pocket, Sly will enter into a stealthy stance, where he is crouching. When attempting to pickpocket, he will stay in place and reach out with the crook of his cane.

In Thieves in Time, Sly's ancestors can also pickpocket guards, using the same default rules as Sly. Sly can also upgrade his pickpocketing technique with the Moving Pickpocket power-up from ThiefNet, which allows him to be able to walk whenever he attempts a pickpocket. The ancestors cannot move while pickpocketing.

Bentley
In Sly 3, Bentley pickpockets with a device called the Pick Pocket Pole, or P-P-P for short. It needs to be assigned to a button (,, or ) via the Gadget Grid, where it is listed as "Fishing Pole," in order to use it. When Bentley is close enough to a guard, hold the assigned button and widen the gap between him and the guard (either by moving back, waiting for the guard to move forward, or both). After getting a certain distance away from the guard, Bentley will pull the P-P-P back, taking some of the pocket's contents. Bentley can also shoot a sleep dart at an enemy and then pickpocket them. The P-P-P is noticeably more time consuming to use than Sly's pickpocketing method.

In Thieves in Time, Bentley uses two robotic arms in his wheelchair to pickpocket guards instead of the Pick Pocket Pole. Here, Bentley's version of pickpocketing is very similar to Sly's version, from the speed of pickpocketing right down to pressing to pickpocket. Also like Sly, Bentley can upgrade his pickpocketing technique with a Moving Pickpocket power-up sold separately from Sly's.

Murray
Unlike Sly and Bentley, Murray's version of pickpocketing is more overt. It does not matter whether Murray has alerted guards or not to pickpocket, unless he wants to pickpocket a flashlight guard, in which he must not alert them. In Sly 3, while behind a guard, uppercut him with, then grab him out of the air with. While in Murray's grasp, press multiple times to shake the guard loose of his coins and loot. If a foe is on the ground and dazed, Murray can stomp to pick up his victim by pressing, before proceeding to press it again to pickpocket. The coins that Murray shakes out of a guard drop to the ground, making it necessary to collect the coins after shaking them out. This can lead to situations where the dropped coins are unobtainable, such as when shaking a guard while facing and standing near open water, or while right next to a wall. If a special loot item is pickpocketed from a guard, Murray will automatically pick it up, so don't worry about losing a high-value item by shaking it out of reach.

In Thieves in Time, Murray retains the ability to pickpocket, but with a few changes. Since Murray cannot perform uppercuts in this game, Murray's stomp has been buffed to allow him to pick up foes in the same way he would an object. As with Sly 3, Murray has to press while carrying a guard to start shaking loose coins. However, you cannot steal loot from guards by default. In order to be able to steal loot, you will need to purchase the Looty Shake power-up from ThiefNet. The coins are also collected immediately upon shaking the guard, as opposed to having to pick them off the ground first.

Trivia

 * Any guard can be pickpocketed, including Carmelita. However, Murray is unable to pickpocket her.
 * In Thieves in Time, Carmelita is the only playable character that cannot pickpocket. This is likely due to her being a member of law enforcement.
 * In Sly 2, Bentley can sell the loot Sly obtains on ThiefNet for coins, while from Sly 3 forward, the items' value is automatically added to the player's coins.
 * Despite not having a hooked end on one side, the Thief Costume's hourglass staff and Bob Cooper's bone club can be used to pickpocket.