Etymology
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shady (adj.)

"affording shade," 1570s; "protected by shade," 1590s; from shade (n.) + -y (2). Meaning "disreputable" (1862) probably is from earlier university slang sense of "of questionable merit, unreliable" (1848). Related: Shadily; shadiness. Old English had sceadlic "shady, 'shadely.'"

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Definitions of shady

shady (adj.)
quiet, dark, or concealed;
her shady past intrigued him
a shady part of town
shady (adj.)
not as expected;
a shady deal
Synonyms: fishy / funny / suspect / suspicious
shady (adj.)
of questionable honesty or legality;
He established a dummy company through which he laundered vast sums of cash from shady middlemen and arms dealers
shady (adj.)
filled with shade;
the shady side of the street
Synonyms: shadowed / shadowy / umbrageous
From wordnet.princeton.edu