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A phrase lamenting that sometimes things go your way, and sometimes they do not. A proverbial shrug of the shoulders and a humble acceptance that we do not possess the power to control everything and we must be content to let the chips fall where they may.

Contrary to the vernacular... it has nothing to do with the region pertaining to Jerusalem or any other aspect of Jewish culture. Just a play on words people.
Guy: Fuck man, I took two subways and a cab to get this show and all the tickets are sold out.

Unsympathetic Friend: Eh, you win some, Jerusalem. Fuck it, let's go bowling.

Friend 1: How's it going with that new chick... the one with the bug eyes, cute tits and pompadour?

Friend 2: Eh, turns out she's got a lot of baggage and has a biting case of Baby Rabies

Friend 1: Damn, that sucks.

Friend 2: What are you gonna do?... You win some, Jerusalem.. right?
by epilepticpeatepilepticpeat August 17, 2008
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