If someone wins a lot of money in the lottery and is called “a lucky stiff,” it means we think of him as a hard-working, average person who got lucky.

But the original meaning of the word stiff described a failure, someone with as much chance of earning that much money on his or her own as a dead person, also called a stiff.

A lucky stiff then means that a person, the lottery winner, in this case, is unworthy and undeserving of monetary gain.

Where Did the Term "Lucky Stiff" Come From, What Does the Phrase Mean, and Why Is it an Insult? …