Pickpocket

Pickpocket activates whenever an opponent makes physical contact with the user through a move, allowing the Pickpocket user to steal the attacker's held item if it isn't already holding one itself. This creates an interesting risk-reward dynamic where opponents must carefully consider whether to use contact moves against Pokemon like Weavile, Grimmsnarl, or Tinkaton. The ability has several important limitations: it cannot activate if the user is knocked out by the contact move, and it won't trigger when the user's own Substitute takes the hit, though it can still steal from attackers behind a Substitute.

The mechanics become particularly nuanced with multi-hit moves, where only the final hit can trigger Pickpocket, meaning the user needs to survive the entire sequence to potentially steal an item. This creates strategic depth in competitive play, as players must weigh the value of their held items against the effectiveness of contact moves. Pokemon with Pickpocket often carry this ability as a deterrent against physical attackers, forcing opponents to rely more heavily on special attacks or non-contact physical moves.

In competitive formats, Pickpocket serves as both a utility ability and a psychological tool. Notable users like Grimmsnarl and Weavile can potentially acquire valuable items like Choice Bands or Life Orbs from careless opponents, while simultaneously discouraging contact-based revenge killing attempts. The ability's presence alone can force opponents to play more conservatively with their item-dependent strategies.