This song is a story, therefore, it has a beginning, a middle and an end.
This song can be hard to decipher because it is not told in linear fashion: the story jumps around. We have to piece it together like a jigsaw puzzle.
Lido is on the run because he had someone's money and instead of returning it, he gambled it away. We can assume Lido's plan was to gamble and win, pocket the winnings and return the original money to its rightful owner (Mafia/drugdealer we can also safely assume). However, he didn't win, and was forced to run, gambling the whole time, having fun, but trying to win enough to be able to give the money back.
But in the middle of it all, they found him, and told him he better pay the money back or split. That scared him and he decided he better head for the border. As Boz Scaggs was from Ohio, we can assume Lido was as well and was heading to the Canadian border, going through Chicago.
Lido is the classic sketchy guy who just can't quit. Just one more.
Lido got some luck just before Chicago. "Grab a handle off the top" refers to money, not booze, as the next line confirms by saying "Lido put THE money down and let it roll." The word "the" refers to "handle", meaning that he won enough in the previous town to bet-it-all and come out even, at least, when he got to Chicago.
The story ends with Lido getting his roll, hitting it big. We have to look back to the first line of the song for evidence: "Lido missed the boat that day . . . But that was all he missed". He won his money back, he can stop running.
This song is a story, therefore, it has a beginning, a middle and an end. This song can be hard to decipher because it is not told in linear fashion: the story jumps around. We have to piece it together like a jigsaw puzzle.
Lido is on the run because he had someone's money and instead of returning it, he gambled it away. We can assume Lido's plan was to gamble and win, pocket the winnings and return the original money to its rightful owner (Mafia/drugdealer we can also safely assume). However, he didn't win, and was forced to run, gambling the whole time, having fun, but trying to win enough to be able to give the money back.
But in the middle of it all, they found him, and told him he better pay the money back or split. That scared him and he decided he better head for the border. As Boz Scaggs was from Ohio, we can assume Lido was as well and was heading to the Canadian border, going through Chicago.
Lido is the classic sketchy guy who just can't quit. Just one more.
Lido got some luck just before Chicago. "Grab a handle off the top" refers to money, not booze, as the next line confirms by saying "Lido put THE money down and let it roll." The word "the" refers to "handle", meaning that he won enough in the previous town to bet-it-all and come out even, at least, when he got to Chicago.
The story ends with Lido getting his roll, hitting it big. We have to look back to the first line of the song for evidence: "Lido missed the boat that day . . . But that was all he missed". He won his money back, he can stop running.
Great song, hit song, happy ending.