Q: If I say, “It wasn’t Jerry,” I mean it wasn’t Jerry. But if I say, “Damn if it wasn’t Jerry,” I mean it was Jerry. How does “Damn if” change the meaning to its opposite?
A: The statement “Damn if it wasn’t Jerry” is short for “I’ll be damned if it wasn’t Jerry.” The idiom “I’ll be damned,” often followed by “if,” is used to express surprise or negation. In this case, both senses are expressed.
Merriam-Webster.com, which labels the usage “informal + impolite,” defines the two meanings of “I’ll be damned” this way:
(1) “used to show that one is very surprised about something,” as in “I spent an hour putting the machine together and I’ll be damned if it didn’t fall apart as soon as I tried to use it.”
(2) “used to say that one cannot or will not do something,” as in “I’ll be damned if I can remember where I left my keys.”
Our searches of newspaper, magazine, and book databases indicate that the usage showed up in American English in the early 19th century but soon appeared in British English.
The earliest American example we’ve found is from a report in an Indiana newspaper about a schoolmaster who killed one of his students.
The 17-year-old victim, who had refused to sit down and watch while the teacher punished his 14-year old brother, had said, “I’ll be damned if I will—I will not see Marcus punished” (the Indiana Palladium, Lawrenceburg, Aug. 2, 1828).
The first British example we’ve seen is from a collection of historical whodunnits set in the courts of George II and George III:
“Why, look at the very position of the fellow as he lies on his bed there: I’ll be damned if it isn’t all sham!” From The Mysteries of the Court of London (Vol. I, 1849), by George William MacArthur Reynolds. The reference is to someone presumed to be feigning madness.
Finally, we should mention that we’ve discussed “damn” several times on the blog, including a 2021 post about how “damn” became a swear word, and a 2019 post on the shrinking of the adjective “damned” to “damn.”