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Related to shadiness: whimsically, shadowiness

shady past

A dubious, suspicious, or potentially immoral or illegal past history. Investigators have begun looking into the shady past of the bankrupt company's CEO. I don't know, John, I wouldn't go out with a guy who has a shady past like that.
See also: past, shady

on the shady side of

slang Older than; more than. I'm much more concerned about my health now that I'm on the shady side of 60. You're on the shady side of 20, which means you need to start acting more responsibly.
See also: of, on, shady, side

shady character

 and a suspicious character
Fig. an untrustworthy person; a person who makes people suspicious. There is a suspicious character lurking about in the hallway. Please call the police.
See also: character, shady

shady deal

Fig. a questionable and possibly dishonest deal or transaction. The lawyer got caught making a shady deal with a convicted felon.
See also: deal, shady
References in periodicals archive ?
Lawlessness, permissiveness, crime, Ryn points out, are everywhere prominent: "Old-fashioned honesty and integrity yield to shadiness and opportunism.
This shadiness of accounting eventuates in a narration that, for all its observational ideals, confuses the roles of reporter, columnist, and editor.
Even as the Enron scandal broke open on January 10, Limbaugh admonished listeners that the true shadiness lay in the way Linda Daschle's clients, American and Northwest Airlines, had benefited from the post-September 11 airline bailout.
The squalor and shadiness of his other responses--alluding to Ms.
But the parties who do not end the shadiness will pay the price.
32) By comparing Romelio's financial dealings with the profits accruing to the erector of a lottery, Webster gives an early indication of their probable shadiness.
Neither did plots 2 and 4 "resemble" each other in shadiness, substrate, or general aspect.
Thus, we have news which tells us nothing about Hancock II but everything about the impeachment of Judith Moriarty because the impeachment story can be handled with a soundbite and because it has implications of shadiness.
I won't miss the shadiness, I won't miss him skulking around after digging someone and I won't miss him saying he has been treated like a criminal, which is utter tosh.
Throughout its first decade, 8990 Holdings has also been changing the game in mass housing by debunking the myths of shadiness, low margins, and risky clients.
Despite its shadiness, the lottery continues to thrive; slogans such as Oregon's "There's no such thing as a losing ticket" encourage us to keep trying our luck.