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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 ?
Dr Simms is definitely the shadiest character I've played on TV.
How can rugby football, with perhaps the shadiest reputation (outside boxing) in contemporary professional sport, now live with the suspicion that it could be a haven for junkies?
I think it's very useful to focus on the supply-side aspect of weapons proliferation, and Gary's work has uncovered many of the shadiest dealings of private firms in the U.
These may by turns be fascinating, outrageous, even bloodcurdling, but in business, even of the shadiest sort, process must inevitably boil down to meetings, conversations, and the preparation of documents.
Gamers live the life of a hustler in Las Vegas in this exciting adventure where a true player will outsmart the shadiest characters, fall in love (or maybe just lust), and become a wealthy high roller.
First footman Thomas is the shadiest member of the household, and a keen thief and liar.
UNDERWORLD is the perfect name for Corrie's knicker factory as it has attracted some of the Street's shadiest bad boys.
Take photos to capture magical moments in your garden and mark out the shadiest spots.
Sometimes the shadiest side yard can be the most charming,'' she says, adding that plants such as ferns, camellias and azaleas will thrive in the shade.
WC established himself as a revered solo artist in 1998, when he issued The Shadiest One that reached Number Two on Billboard's Top R&B/Hip-Hop Albums chart.
Zarzis is known as one of Tunisia's shadiest corners with 500,000 palms and 100,000 olive trees.
He discovers that Klaas's small garbage and sewage business has grown into a powerful cleaning and recycling conglomerate; that sometimes toxic chemical waste is potent enough to kill anything it touches; that Klaas will not tolerate such illegal dumpings which pollute the ground (hence the title Smoarge Grun or "Polluted Ground") but that his sons, who have taken over the business, honor profits more than their father; that the shadiest character in the whole business is Jef de Hondt, the company manager, an import from the South with suspicious connections to the Mafia; that Klaas was in the process of gathering soil samples for testing when the "accident" occurred.
In the shadiest areas grow Campanula rotundifolia and coral bells.
com features selected by Lycos are "Bill Bilkman," an animated series about the world's shadiest deal maker -- whatever Bill wants, Bill scams; "Open Mic," which features the shticks of Hollywood's finest underground comedians, whom the audience can interactively heckle or applaud; and the animated serial "Crispy and Root," starring a couple of wrong-way drivers on the Information Superhighway.
On Italian holidays, I would tend to seek the shadiest route, and a couple of times in Florida I have found anything over 30C debilitating and sought the air-conditioning.