work both sides of the street

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work both sides of the street

1. Literally, to occupy positions on both sides of a single street in order to sell something to people walking on either side. Our sales were doing OK, but it wasn't until I hired a second food truck and started working both sides of the street that things really took off.
2. To aid, support, or engage with both sides of some issue, situation, agenda, competition, etc. Usually used with the implication of doing so in a duplicitous manner to benefit one's own interests or agenda, though not always. She was accused of working both sides of the street, acting as a legal adviser for groups trying to legalize recreational cannabis while also serving on the board of several organizations that have tried to quash such actions. Look, I've been working both sides of the street in Washington for years, negotiating the rather volatile divide between corporate and political interests very carefully.
See also: both, of, side, street, work
Farlex Dictionary of Idioms. © 2015 Farlex, Inc, all rights reserved.

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.
See also: both, of, side, street, work
The American Heritage® Dictionary of Idioms by Christine Ammer. Copyright © 2003, 1997 by The Christine Ammer 1992 Trust. Published by Houghton Mifflin Harcourt Publishing Company. All rights reserved.

work both sides of the street

To engage in double-dealing; be duplicitous.
See also: both, of, side, street, work
American Heritage® Dictionary of the English Language, Fifth Edition. Copyright © 2016 by Houghton Mifflin Harcourt Publishing Company. Published by Houghton Mifflin Harcourt Publishing Company. All rights reserved.
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