bamboozle

First recorded in 1695–1705; origin uncertain

Bamboozle is one of those words that has been confounding etymologists for centuries. No one knows for sure what its origins are. One thing we do know is that it was originally considered “low language,” at least among such defenders of the language as British satirist Jonathan Swift, who hoped (and predicted) that it would quickly fade from the English lexicon.
The earliest meaning of bamboozle was “to deceive by trickery, hoodwink,” which is why some believe that it arose among the criminals of the underworld. One colorful, but unlikely, theory has it that bamboozle comes from bombazine, a kind of fabric that, dyed black, used to be worn for mourning. One has to imagine black-bombazine-wearing widows in the mid- to late 17th century bilking young gentlemen out of their purses.
By 1712, it had acquired the sense “to perplex; mystify.” It is not known for certain, but this sense might have emerged under the influence of the Scottish word bumbaze (or bombaze), meaning “to confuse,” similar in both sound and meaning. Given the befuddling qualities of alcohol, it's not too surprising to find that, in the 1800's, bamboozle showed up on college campuses as a slang term for “drunk.”
Far from slinking into obscurity, bamboozle today has left its lowly roots behind and found a secure place in the lexicon of standard English. Its very longevity stands as a reminder that you can't predict or enforce the fate of a word.

— Bamboozle: A board game by Milton Bradley introduced in 1876, notable for featuring the first large folding game board.
— Bamboozle: Milton Bradley introduced another board game with the same name in 1962. This game was based on the 1962 NBC-TV show McKeever and The Colonel.
— Bamboozle: A Parker Brothers (now Hasbro) game from 1997. It is a word game in which one team has to guess the words that another team came up with based on a list of randomly-generated letters.
— Bamboozled: A feature film (2000) directed by Spike Lee, about a frustrated African American television writer who proposes a minstrel show as a form of protest, which unexpectedly becomes a hit.
— The Bamboozle: An annual three-day music festival held in New Jersey.

C18: of unknown origin