slyboots

• sly-boot, sly-boots, slyboot

From sly +‎ boots.

slyboots (plural slyboots)

1. (chiefly British) A person who is clever or shrewd, especially one who is stealthy, manipulative, and rather charming.

   Synonyms: artful dodger, con artist, operator, rogue

   • 1838 July 24, Ralph Waldo Emerson, “Literary Ethics. An Oration Delivered before the Literary Societies of Dartmouth College, July 24, 1838”, in J[ames] E[lliot] Cabot, editor, Nature, Addresses, and Lectures (Emerson’s Complete Works; I), Riverside edition, London: The Waverley Book Company, published 1883, →OCLC, page 166:

     But Truth is such a flyaway, such a slyboots, so untransportable and unbarrelable a commodity, that it is as bad to catch as light.

   • 1857–1859, W[illiam] M[akepeace] Thackeray, “Troubles and Consolations”, in The Virginians. A Tale of the Last Century, volume II, London: Bradbury & Evans, […], published 1859, →OCLC, page 283:

     "Oh, you sly-boots!" says the Countess. "Guess you come after the old lady's money!"

   • 1922 February, James Joyce, “[Episode 15]”, in Ulysses, Paris: Shakespeare and Company, […], →OCLC:

     You're such a slyboots, old cocky. I could kiss you.

   • 2000 April 4, Chris Sheridan, “If I'm Dyin', I'm Lyin'”, in Family Guy, season 2, episode 9:

     Peter: All we gotta do is tell a little white lie. Just go with it. [dials phone] Is this the Grant-a-Dream Foundation? My son Chris is dying!
     Chris: Holy crap, no! Oh, my God!
     Peter: That was the lie.
     Chris: Oh, you slyboots.

   • 2004, Umberto Eco, Geoffrey Brock, transl., The Mysterious Flame of Queen Loana, New York, N.Y.: Harvest/Harcourt, page 54:

     This slyboots took me for a ton of money, made me do whatever she wanted.

   • 2015 November 1, Hendrik Hertzberg, “That G.O.P. Debate: Two Footnotes”, in The New Yorker‎^[1]:

     Cruz was obviously analogizing Bernie Sanders to the Bolsheviks and Hillary Clinton to the Mensheviks. The oleaginous Texan is an erudite slyboots, but his history is off-kilter.