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A trade completed by an NBA executive who is a former champion of the club he's trading his player(s) to. Usually Wingman Trades are massively lopsided, appearing to make one party seem like a "wingman" who completely screws himself over for the benefit of his buddy who reaps the rewards/nails the prom queen.

Recent Wingman Trades include KG to Boston, and Gasol to LA.
Lakers fan: "Dude! Did you hear? Gasol got sent to the Lakers for absolutely nothing! How the f--k did they pull that off?!"
Grizzlies fan: "Wingman Trade. F--k you"
by TTBlogger February 05, 2008
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