work both sides of the street

1. Engage in doubledealing, be duplicitous, as in The real estate agent was known for working both sides of the street, advising first the buyer and then the seller. This metaphoric term transfers opposite sides of a street to opposite sides of a negotiation.

Example Sentences

“You can’t work both sides of the street,” he said.

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Kennedy seems concerned that a neutral expert can’t be effectively helping both sides, and Bright agrees that mental health experts “can’t work both sides of the street.”

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“I think what they did drove him away from politics, but it drove him toward film and I think that’s to our benefit … he could work both sides of the street, so to speak, and he has and he’s done it beautifully.”

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“You can’t work both sides of the street,” he says.

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The C.I.A. could cultivate relations with opposition groups secretly, and this permitted the American government to work both sides of the street.

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