this post was submitted on 04 Feb 2024
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https://archive.org/details/cassellsdictiona00gree/page/884/mode/2up I've seen several sources pointing to this particular dictionary, but I'm not familiar enough with Internet archive lending to pull the specific page. I also haven't found any primary sources from that time period to correlate.
Its much more recent, but 50 Cent used it in a number of songs, including 2005's "in my hood"
Sorry, the claim that "out of pocket" has this alternate, non-financial definition going back to the 1940s is entirely unsupported.
There are four references to "out of pocket" in the book, according to Google Books. All of them have to do with money. https://books.google.com/books/about/Cassell_s_Dictionary_of_Slang.html?id=5GpLcC4a5fAC
If you look at the 50 Cent lyrics in context, they're saying that crack money has slowed down, so the "bitch" is paying out of pocket. https://genius.com/50-cent-in-my-hood-lyrics
Edit: on reflection, I'm not sure I understand the lyrics well enough to say which way he means "out of pocket" to be taken.