How esoteric can we get? A stumper!
Who’s been an American longer, a Pensacolan or a St. Augustinian?
If you guessed the folks in St. Augustine, you’d be right, but possibly for the wrong reason. St. Augustine officially became American on July 10 1821 along with the territory known as East Florida. Pensacola, in west Florida, became part of the U.S.A. a week later, on July 17 1821.

Have you ANY idea how hard it was to keep those trousers white in 1821?
If you didn’t attend grade, middle, junior high or high school in Florida, you’re possibly mighty confused about what country claimed Florida when. Here’s a quick rundown.
Reference: https://publications.newberry.org/ahcbp/map/map.html#FL