Outrageous impostor! fool, dotard, oaf! Did he think to bejuggle me with his preposterous gibberish!
Mardi, by Herman Melville, 1849.
Since we moderns know juggle only to mean expertly tossing a number of things in the air and catching them, this antique word will puzzle us. That’s because down the centuries jugglers have become more specialised.
When the word came into English, getting on for nine centuries ago, it had the same sense as its French, Italian and Latin forebears: a jester, one who amuses through stories, songs, tricks and clowning. The Latin source was joculator, from joculari, to jest or joke. The first of these has bequeathed us joculator, a jester or minstrel, now obsolete; from the same source came the better-known jocular and jocund and their relatives.
Over time jugglers became less and less general entertainers. They set aside their music and stories and became exclusively conjurors, in particular that sort who deceives his audience by legerdemain or sleight of hand. It was only at the beginning of the nineteenth century that they came exclusively to practice the specific type of manual dexterity that we now associate them with (as an historical note, later in the same century the first edition of the Oxford English Dictionary didn’t include this sense of the verb juggle because the word hadn’t yet acquired it).
By the sixteenth century, the verb had developed the negative ideas of a man who deceived in earnest, not just for entertainment, who tricked or cheated another. The be- prefix was added to it in the seventeenth century to suggest that the process was happening thoroughly or excessively.
From the Spanish school of comedy came these three-ply intrigues, intricate plots, and continual disguises that weary and bejuggle the modern reader.
Portraits and Backgrounds, by Evangeline Wilbour Blashfield, 1917. The sense has here softened towards mere confusion rather than outright deception.
[Many thanks to Daniel Matranga of the Adriance Memorial Library in Poughkeepsie, NY, for introducing me to this word.]