"Now on the one hand, why should we trust a broke gambler? This guy can’t possibly have anything to teach us. But it’s precisely BECAUSE the man is broke that his advice means something. The song is more about loss than it is about winning. (I really love the line “Know when to walk away… know when to run.” There’s a little joke there, since you expect the second half of that to be the OPPOSITE of “walk away,” a la “hold ‘em/fold ‘em.” But I think the writer is also telling us that you’ll be folding MORE than holding, in cards and in life. You should play very cautiously.)
I think the gambler isn’t so much telling us how to win at life, but how to bear loss gracefully. One must have the humility to run, and the zen not to dwell on how our chips have dwindled to a pitiful little stack. I see two guys in a train car, the narrator who thinks he’s got it bad, and the gambler who has it even worse. The narrator is depressed, but the gambler is not. The gambler is telling him how to let go of that worry."