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RakeStepping is the where a person or company keeps making the wrong decision no matter what they do.

The term was created by Ricky and Eliot at Internet Today and was used on an episode of News Dump. The term comes from the Simpsons Episode "Cape of Feare" when which Sideshow Bob keeps sanding on rakes no matter what turn he makes.
Oh man Trump keeps on RakeStepping; everything that man does is the wrong decision.
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by Rjf4590 July 12, 2020
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Apr 20 Word of the Day
A term used to reference cannabis/marijuana/weed.
This Jazz Cabbage got me zooted. Jazz Cabbage is less harmful than Squares. I’m smoking that Jazz Cabbage boy.
by Gypsiehood97 December 30, 2017
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2
A situation that people seemingly can't do anything right, and every choice appears worse or just as bad as the one already made.
The band formerly Lady Antebellum rake stepping their new name when they found out there was already a Lady A., and decided to sue her.
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by Ardent_drub July 12, 2020
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3
The instance in public relations for a company, individual or any other organisation cannot act in anyway that aids their defence! The name is in reference to the Simpsons Character Side Show Bob stepping on rakes! Implying that those “RakeStepping” cannot put either foot forward without hitting themselves in the face with a metaphorical Rake!
Did you see insert celebrity here online today their PR team just can’t stop RakeStepping!
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