Deep Pocket As A Slang Term
The term “deep pockets” (also given as “deep pocket” and “deep pocketed") is attested sparsely in the 1940s through the 1960s, but became popular with the litigation explosion of the 1970s.
A person with “short arms” and “deep pockets” is a person (sometimes derided as “miserly” or “cheap") who saves money and doesn’t often spend it. The term “short arms and deep/long pockets” is cited in print from at least 1952.
In Ireland, this phrase was attached to a wealthy business man from Tipparary who, upon his round of drinks, would break his glass on the floor, knowing the owner of the pub would ask him to leave. This was also called the “O’Shea Fiddle”.
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