Slang definitions & phrases for work both sides of the street
work both sides of the street
verb phrase
To take two contrary positions at once; have it both ways: Most politicians have a good instinct for working both sides of the street
[1930s+ Politics; probably fr the notion of a hoboes' or beggars' agreement to parcel out the territory]
Idioms and Phrases with work both sides of the street
work both sides of the street
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.