Where does the phrase "out of pocket" come from?

That's an odd usage. (Then again, I use plenty of words strangely.)

I've only ever heard it used in the context of "Out of pocket expenses" -- as in, expenses to be reimbursed later, or "out of pocket cost" -- meaning the cost prior to rebates.

http://www.randomhouse.com/wotd/index.pperl?date=20010522

Interesting, I've never heard of that usage either, but it appears to be so.

That's a fantastic link...

i've also only heard the use where the phrase made literal sense -- like the money is coming from your pocket, out of your own pocket (assuming that's where your wallet is, of course)

I think it was penned by Damon Runyon in the roaring twentys, he has a ton of verbage to his credit

I hear people in my office say it all the time if someone is travelling or otherwise unreachable. For some reason I had always assumed it was a term coined by bodyguards to discreetly let someone know that the person they were protecting was missing/vulnerable/out in the open. But then again, I’m never been a secret service agent, so I don’t know at all

I believe the phrase is used in business today to signify that a person is out of the office (not able to be reached on their office phone) but is available at their cell phone number (the phone in their pocket).

Current thinking is that it relates to the football formation, wherein the quarterback is “in the pocket.” Thus, to be “out of pocket” is to be away from team mates. The Word Detective column thinks this is viable. I tend to concur.

Out of pocket – money I have to spend that came out of my pocket.