Ok, great film, but...

I often wondered this myself. I had to watch the movie several times before coming up with the logical answer.

Jimmy has 5 in his crew because that is actually what is needed (not really, but just to be on the safe side). For instance, the two cops would pull the kid over, 1 guy is the lookout for the real cops and other dangers, while Jimmy and another guy sit in the truck also looking out for trouble and waiting for the kid. For instance, if the kid had a gun, had some extra guys with him, the real cops showed up, etc, then the plan would really get messed up if there were only a couple of guys.

They were supposed to scare the kid, probably all get in the back of the truck with him and threaten him and scare him so bad that he wouldn't even mention it to the girl. I think the writer even made him such a cocky little prick, just so you would know that it would take a lot more than 2 fake cops to scare him enough to stop seeing the girl.

Critical Bill wasn't even supposed to be involved, he was supposed to be a "wingman." He was supposed to sit in the truck with Jimmy incase of trouble, and then he would come in and kick everyone ass. An enforcer.



As far as Jimmy picking such a rag tag group, if you rewatch the film, you will notice that they keep referring back to the "old days" when this and that happened. "Boat Drinks!" These guys were all friends and Jimmy trusted them and felt like he owed them something for being loyal, not being a rat, etc, in the past. He can't really bring in new people who he might not be able to trust, so it's them or nothing, and he HAS to get this job done, because he owes The Man with The Plan.

It even mentions in the movie that there was never a better WINGMAN back in the day, than Critical Bill. Like I said before, he was supposed to be in the truck with Jimmy, but he caved after Bill begged him to be one of the cops.

All this is really explained later in the movie, as you see Jimmy refuse to leave any of these guys behind (remember, The Man tells him to get out of Denver while he takes out the rest of the crew). Instead, he chooses to sell his boat and make a play to get all of them out alive.

"But what I find confusing is why he took such idiots along with him - it's pretty obvious that 'fecal freak' was going to lose it, and like he said - it was the Saint's fault for taking him. Someone who beats up corpses for fun cannot be considered capable of rational control or judgement. "

It shouldn't be confusing- first of all- it was not something that should have required highly skilled hit professionals. I think the "action" was on the order of what would involve lower level enforcers. (they were just supposed to "scare" him.) It should have been easy.

These guys were his friends from "back in the day"- and it wasn't a complicated job. Since we know Jimmy is loyal- I think its safe to say he involved them because he knew they all could use the cash- and he didn't want to compromise their personal honor by just handing them money. So he involves them so they would feel like they "earned" it, and keep their self respect. Jimmy knew Bill was a nutter, but he thought he could contain the situation, and he was loyal enough to want the "crew" to be together again, and not have one feel left out. This movie isn't really about a botched mob hit- its about friendship.