Character/storyline clash

I think that it's basically that they're all old and tired and want out of the business. Critical Bill is young and brash and gets himself in trouble, and Pieces just doesn't know what to do when things go down the way that they do. It's kinda like Resoviour Dogs - they're all mostly old dogs in the game, but there's always someone who just wants some action and that's all he's going in for. Overall I think their stories are just pointing to the fact that sometimes you're in the wrong place at the wrong time and all the know-how in the world can't get you out of it.



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"There are worse things in life than being wet, so let us get on with it."
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I would probably have to watch it again to be sure, but I think that (in the movie) they may have alluded to some previous job that had gone wrong - perhaps the one that forced the members of the crew to go into early retirement from the crime business, and become "Citizens"...

This may relate somewhat to how or why The Man was able to get Jimmy to come in for this one last job... I believe he said something along the lines of "I gotta call in the note." I may be heading down the wrong track on this one, but I would assume that this "note" is some debt incurred due to either some past failure or mistake on Jimmy's part, or some favor ultimately owing to The Man.

Other references to past events that may or may not be of some significance are, for example, when The Man advises Jimmy to visit the Vatican and "pray to the God that you abandoned back in Brooklyn." Or a reference made by Franchise to when The Man was shot (hence his current physical state). Several references are also made to jail time done by the various members of the crew, hence the special handshake they do, Critical Bill and Easy Wind's ongoing differences about the whole "fecal freak" issue, and Pieces' reference to having done a little too much time (when he reflects upon his life near the end of the film), among others.

Ultimately, if I am on the right track, this job (and therefore the main plot) is about redemption.

This is why I believe that Jimmy chose to call in the crew, despite their growing differences and initial reluctances to re-enter the world of crime, as well as their unsuitabilities to this particular action (i.e. Pieces' physical condition, and Critical Bill's mental instability).

Why Jimmy allowed Critical Bill to play one of the Cop parts is simple. In his own search for redemption, Jimmy allows Critical Bill the same opportunity to redeem himself by putting him in a position where he would be able to prove to them and himself that he had indeed changed, just as he had assured them.

Basically, I think that it is wrong to assume that they are a crew of experienced criminals, competent, and that they or Jimmy therefore know exactly what they are doing... I believe that if they really were as capable and experienced as Jimmy's facade may lead you to believe, that they would not display such a huge reluctance to re-enter the criminal world, or leave it in the first place for that matter. Rather, they are essentially the bunch of misfits they are described as in the film, a group of ordinary guys placed in an extraordinary situation.

Compare the likes of Jimmy, Franchise, Pieces, Easy Wind, and Critical Bill to the characters of The Man and Mr. Shhh, and the distinction becomes much clearer... The crew are bound my morals and loyalty. Mr. Shhh is bound by professionalism... And in his own words, The Man states that "I'm a criminal, my word don't mean dick."

First of all, I think the loan theory is completely wrong, and makes little sense. Jimmy does not accept this job because he owes The Man money. If the job were a repayment for some financial debt, then it would be completely illogical that The Man With The Plan would reward Jimmy The Saint with payment upon completion. If the job were merely to repay a debt, then Jimmy would have received nothing for completing it.

Also, the redemption most definately does come into the story before the buckwheats are ordered. In Bill's sob story, he clearly states that Jimmy got the opportunity to change, so why shouldn't he? That right there is an allusion to redemption, and is exactly what I was referring to. Assembling his old crew is not simply to ensure that the job goes smoothly, and this is plainly shown when tensions arise even before the crew has properly discussed the action. Rather, by assembling his old crew, Jimmy is hoping to give each of them an opportunity to rise out of the situations they have found themselves in. They could all benefit greatly from their share of the money, particularly Franchise and Pieces, as well as from the restoration in self-esteem that successful completion would bring to them. Remember how Jimmy convinced Pieces to sign on by telling him that The Man had specifically mentioned his name?

When the job goes bad, Jimmy feels personally responsible for the fates that are brought upon each member of the crew, because only he was given no choice. The quest for redemption does continue, even more desperately, from this point. That much you did pick up on, but it is incorrect to say that redemption played no part in the story leading up until that point. Sheer dumb luck is not the theme of this movie. Misplaced faith and loyalty, as well as debt, are the factors that contributed to the entire group's demise.

You are correct in concluding that "the God you abandoned back in Brooklyn" is a reference to Jimmy leaving the Seminary. As for his nickname Jimmy The Saint, I think that your reasoning is a little misguided. When he claims that he says nine Hail Mary's at bedtime, he is merely joking, when asked to explain his nickname. Rather, the nickname refers to his good nature and moral fibre, traits that are uncommon amongst criminals in the underworld. The Man's son alludes to this, while repeating "Jimmy The Saint", and suggesting that he is noble. Jimmy The Saint feels guilt and regret, is loyal and forgiving, and keeps his word. When he commits some sin or transgression, his own remorse is painfully depicted. He is perhaps too nice for his own good, and it is this quality which leads to his undoing. It is why he did not have the heart to refuse Critical Bill's heartfelt request, and is also why he did not take his chance to escape, but rather stayed in Denver to try to help the friends he endangered as well as help Lucinda by giving her the child she needed to escape.