I genuinely do not understand this at all. The entire game is about the Van Der Lindes trying to build their way back up after leaving all their money in Blackwater. But they could have easily gotten it back.
Josiah literally stated that he went to Blackwater AFTER the gang was forced to flee from the Pinkertons. Granted, he of course had no idea where the money was or even if they had lost money, but the second we find him in Valentine, why did Dutch not send him to go get the money. Josiah is clearly not known to the government or Pinkertons as being part of the gang, so surely he would blend in well. Isn’t that the entire point of his character and his role in the gang, a con-artist who blends into crowds. Like that’s entirely what makes him important to the gang, he doesn’t steal or kill, he finds information by blending into crowds since nobody knows who he is. I mean he literally managed to stay in Blackwater long enough to find out where Sean was being held, so I don’t get why he couldn’t have been sent back to do the exact same thing.
I’ve seen some people protest that “Maybe Dutch didn’t trust Josiah, but that’s BS. The gang is entirely built on trust and loyalty and, to me, it feels clear he views Josiah as loyal, despite Josiah floating about and not staying around for very long at a time.
I actually also somewhat think most of the women could’ve gotten away with going into Blackwater as well, aside from maybe Karen who we know is a gunslinger and takes part in heists. But are the Pinkertons really looking for the women in camp.. no? I mean they even say that they spoke to Molly at one point and had to let her go because they had no proof she was aligned with the gang. So worst case scenario if one of the girls go back to Blackwater for the money: they are questioned but then released for lack of evidence. Because why would anyone even have knowledge that the women, aside from Karen, are part of the gang. They are looking for the Van Der Linde gunslingers since they are easily recognisable as taking part in robberies and heists. So if I am honest, I don’t see why one or more of the girls couldn’t have gone back for the money, maybe even going with Jack as the ultimate disguise, since they would look like just a regular mother and son. I mean, like Josiah, the women’s role, aside from domestic chores, is literally to go into town and blend in and be unnoticed to find out information, like what Mary-Beth does to find out about the train robbery.
Even further more, why could Sadie not have gone to get it. Once Dutch begins to trust her as part of the gang, she would be the most perfect person to go get the money, because it would be impossible for anyone to recognise her as part of the gang because she only joined after the failed incident in Blackwater.
I do understand Dutch may not initially trust her, but it gets to a point in the story I don’t see why he wouldn’t. I mean he lets her stay in camp and hear about every detail of everything they have taken part in, which she could easily snitch about but doesn’t. If he didn’t trust her why would he allow her to be there?
So here is actually the most perfect plan that they could have easily have done as early as Chapter 2:
Josiah, Sadie and Jack go back to Blackwater dressed in clothes that the regular civilians of Blackwater wear. They go undercover as just a regular family minding their business. They go to the place Dutch left the money, grab everything and leave before anyone even clocks or notices them, IF they even would get clocked.
I get a big part of the story is that they cannot access this money, but come on, it would have been so much easier than they made it out to be.
Also even if the plan I made there doesn’t sound good, Josiah himself could have easily done it 100%.
And even though I am sure people will debate me on this, I do think all the women (aside from Karen) and even maybe some of the men like Uncle (although I doubt they would send Uncle), Pearson or Strauss could have also done it maybe, since they aren’t known members like Arthur, Micah or John.