From The Book of 500 Curious Puzzles, 1859:

A blackleg passing through a town in Ohio, bought a hat for $8 and gave in payment a $50 bill. The hatter called on a merchant near by, who changed the note for him, and the blackleg having received his $42 change went his way. The next day the merchant discovered the note to be a counterfeit, and called upon the hatter, who was compelled forthwith to borrow $50 of another friend to redeem it with; but on turning to search for the blackleg he had left town, so that the note was useless on the hatter’s hands. The question is, what did he lose — was it $50 besides the hat, or was it $50 including the hat?

This is not so much a puzzle as a perplexity. “[I]n almost every case the first impression is, that the hatter lost $50 besides the hat, though it is evident he was paid for the hat, and had he kept the $8 he needed only to have borrowed $42 additional to redeem the note.”