"Hoodwink" reflects an obsolete meaning of "wink." Today, "to wink" means to close one eye briefly, but during the 1500s it meant to shut both eyes firmly. So a highwayman who placed a hood over a victim's eyes to effectively close them, was said to "hoodwink" his prey, and soon "hoodwink" came to mean "to dupe."

Why is it called hoodwinked?

A now-obsolete sense of the word wink is "to close one's eyes," and "hoodwink" once meant to cover the eyes of someone, such as a prisoner, with a hood or blindfold. ("Hoodwink" was also once a name for the game of blindman's buff.) This 16th-century term soon came to be used figuratively for veiling the truth.

Where did the term bamboozled come from?

The word bamboozle allegedly comes from a French word, literally meaning “to make a baboon out of someone.” The word bamboozle first appeared in the language sometime around 1700.