Used when one person has a strong influence over another, often in politics or business settings. He managed to get the contract approved; he clearly has someone important in his pocket.
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Negative Connotation
Carries a negative implication, suggesting corruption or unethical behavior. You can't trust her decisions; she's got too many regulators in her pocket.
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Not Literal
It's a metaphorical expression, not meant to be taken literally. With the media in his pocket, his public image remained untarnished.