Use 'pick somebody's pocket' in situations where stealth or slyness is involved, like a thief in a crowd.

Context Matters

This phrase should be used when referring to the physical act of stealing from someone's pocket silently.

Literal Action

Saying someone 'picked a pocket' could sound accusatory, so be cautious when using it.

This definition is not about literal stealing but taking money in deceitful ways like overcharging.

The phrase often implies criticism towards entities perceived as greedy or manipulative.

In this usage, the 'pickpockets' aren't real thieves but are metaphorically similar.