Lyric discussion by ReverendJohn 

So, heres my basic analysis and some questions I have:

Lido is a small time hustler and gambler. He's fed up with his life, maybe he suffered some setback (Lido missed the boat that day) so he leaves his home town (he left the shack But that was all he missed and he ain't comin' back) (where ever that may be, Tombstone, Arizona? from the reference to the tombstone bar). He heads to Chicago (Chi-town), intent on winning big playing craps (put the money down, let it roll).

A handle is a bottle of liquor, in case you didn't know. I just learned that recently.

He just wants to win big once and then he's out (He said one more job ought to get it, One last shot 'fore we quit it, One more for the road)

Apparently things are going well for Lido, (Lido be runnin', havin' great big fun) until he gets a note from his girlfriend or wife telling him to shape up or she's leaving him (until he got the note Sayin' toe the line or blow, and that was all she wrote) at which point he quits gambling and eagerly heads home with his winnings (He be makin' like a beeline, headin' for the borderline Goin' for broke)

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