Typically a hornswoggle includes money but is not required. "J.A. hornswoggled more than a dozen of us with his scheme to develop property in the Sonoran Desert."
Some synonyms for hornswaggle would be along the lines of a deception. To play a trick on, fool, make one look silly, outsmart, bluff, sham, fudge, outwit, hoodwink, wheel and deal, sell a gold brick, fake someone out, diddle, bamboozle, make a wally of, and rip off.
The American Heritage® Dictionary of the English Language says that they aren't really sure where the word originated but think it may have been in the northen and western areas of the US. Perhaps as a way to poke a little fun at greenhorns from back east. "Hornswoggle" first appeared in print in Kentucky in 1829 probably from Mathews' 1829 Beginnings of American English: "Hornswoggle, to embarrass irretrievably."Why there's even a joke to be found online about a hornswaggle of another kind.
- Two women in a one horse town both had daughters, each of marriageable age. But there were no prospective husbands in town due to shootings, running off with outlaws and drunk riding. And there was no chance at all of any bridegrooms turning up.
The two mothers pooled their meager resources, advertised, and sure enough, they got results: twin brothers in the next town were looking for wives. The twin bridegrooms were sent for but along the way they met up with outlaws. One was killed, but the other escaped. Upon his arrival, the mothers were in immediate conflict as to whom the surviving twin belonged. They were going to kill each other over it. After all, each had a daughter's future at stake. They took the case to Judge A.K. Hornswoggle, alcoholic, disbarred, but with Solomonic frontier wisdom.
After due deliberation, Hornswoggle ruled that the young man be chopped in half and one half awarded to each daughter. The first mother was outraged. If Hornswoggle wasn't drunk or stupid, he was a monster for suggesting such a thing. The second mother thought it would not be a bad solution. And pointing to the second mother, Hornswoggle said, "Your daughter gets him. You're the real mother-in-law."
A Dictionary of the Old West by Peter Watts published in 1977 relates this interesting but hard to pin down explanation. According to him, a cow that has been lassoed around the neck with a "catch rope" will "hornswoggle" that is it will twist and wag its head around frantically in an attempt to get free of the rope. A cowboy who allows the cow to succeed is then said to have been "hornswoggled." Perhaps it's the horn part of the word that brings to mind steer wrestling, or maybe because it sounds like hogtied . Charles Earle Funk points out in Horsefeathers and Other Curious Words (1958), turn-of-the-century Kentucky is well known for a culture of frontiersmen who were always trying to outdo each other with "highfalutin words."Still it's a handy word to have around and I kind of like the way it rolls off the tongue.