A shady contractor is someone who can talk up a storm while low-balling you i.e. makes a deal or arrangement that sounds good but really isn't.
"Rick was talking to me about all these small boxes that he had to move and how easy a job it would be for two people and that he would do most of the work, but when I went with him to help him all of the boxes were super heavy and we had to move them up sooo many flights of stairs and it took soo long."
"Damn! What a shady contractor!"
"Damn! What a shady contractor!"
by Shammmm June 14, 2015

Imagine if u put an xxxtentacion sadboi fan in a League of Legends game maining rengar because theyre a self-proclaimed cat-lover. This aint it cheif
Person1:i feel kinda down today man i dont wanna talk about it
Shady Gay:shut up gayass x's new song went platinum
Shady Gay:shut up gayass x's new song went platinum
by Reposted_Shaggy April 28, 2020

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