Everybody knows that phrase, right? It means, more or less, he's down and out, had a run of bad luck, looking for a job, lost his house, his business, whatever.
Last month I read Dos Passos' USA, a massive novel that covers the history of the US from about 1900 to 1930. Dos Passos uses that phrase frequently in the book.
Now I'm reading Thomas Wolfe, You Can't Go Home Again. He uses the phrase, or a variation, as well.
It took me a long time to realize what the phrase actually refers to. When you're on your uppers, it means you've worn the soles off your shoes. All that's left are the uppers.
That's getting poor.