Lyric discussion by tuxrose 

A man with something serious troubling him finds himself sharing a compartment on a late night train with a processional gambler. Whatever’s weighing on him must be big, or why else would he be draining a bottle of whiskey on a midnight train with destination unknown? (“A train bound for nowhere.”) Probably something about a woman, knowing these old country and western songs…

They sit in silence for a long time, until the gambler breaks it, saying: “I’ve built a life on reading people’s faces, and I can tell looking at yours that you’re up against something that’s bigger than you can handle. If you’ll share that last swallow of whiskey and a smoke, I’ll give you some advice.”

The nameless companion relents, and in the thick gambling metaphor of the chorus, the gambler tells him, basically this: That there are times you need to hang on, and times you need to let go; and also times when you need to swallow your pride, think about what you’re up against, and get the heck outta there as fast as your legs can carry you.

He repeats more of the same metaphor in the second verse, and also reminds his companion that like gambling, life is a matter of chance or luck (“Cause every hand’s a winner, and every hand’s a loser”) and that the best you can expect in the long run is to break even, and die happy (“in your sleep”). Then the gambler, old enough to call his companion “son”, and hit by the effects of the whiskey shot, falls asleep in his seat.

And as the nameless companion sits looking out the window in silence, the gambler’s advice repeats in his head (as the chorus repeats in the song) he reaches an epiphany; something about what the gambler said clicks in him, and he understands how he needs to deal with his problem. (“And in his final words I found an ace that I could keep” — the “ace” the gambler hinted the man was missing at the beginning of the song.)

How did the gambler break even? That one’s a little bit more difficult because it’s outside of the flow of the song’s narrative about the nameless man travelling on the midnight train. But, it might have to do with the fact that as a professional gambler the man giving the advice has made a living by taking what’s valuable from other people. On the train, he is giving his nameless companion powerful, but cryptic advice that guides him to the answer to his troubles. He’s giving away something valuable rather than taking it; or at least selling it, if you consider the whiskey and the cigarette payment.

not too cryptic. the narrator does say, "in his final words i found. . . " right after he said the best you could hope for was to "die in your sleep".

not being smart, just seems a little obvious. otherwise, interesting insight. hadn't looked at the overall song that way before.

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