There are very few characters who are able to call out the gang's hypocrisy from the beginning of the story. And I'm not talking about admitting that Dutch is changing, but rather a complete acknowledgement of the flaws in Dutch and Hosea's philosophy.
First is Charles while riding with Hosea, who was talking about the natives in the area.
"How do you rob and kill people pleasantly? We don't, in spite of Dutch's talk"
He's skeptical. Not because he's able to see their impending downfall,but because he hasn't been introduced into the gang with the same narrative that most others have. He wasn't saved by Dutch and wasn't spoon fed a philosophy from a young age by either him or Hosea. He's a survivalist with a moral compass which happens to align in with theirs. This is also the reason he calls out Arthur when he sees fit.
In the same branch, Lenny doesn't out right critiques Dutch's words. But he does question Evenly Miller, very heavily. It's obvious that Lenny is an educated man, and it frustrates Dutch that he sees right through the empty words of his favorite author.
"He speaks very prettily, but doesn't say anything new" and "he's a rich dreamer playing to be one of us"
Unlike Charles he doesn't do it with the intention of calling out behavior, I don't think he even tries to debate Dutch on the matter, he's just thinking out loud.
It's interesting the different reactions to both Dutch and Hosea being "Called out".
Dutch get defensive or upset, repeating the same beliefs and justifying them, he's not used to being outsmarted, he's unsure on how to react in a way that would still benefit him. Violence would make him seem primitive when it's a battle of intelec, and if his smart mouth is not going to suffice.
Hosea also gets a little defensive, he puts the blame on "trying to simplify a complicated manner" to Arthur, he's reluctant to show he's wrong, he's deflecting.
While we do not see Lenny have these debates with Hosea, we see Hosea constantly motivating Lenny to go to college and get educated. Which means Lenny has shown his smarts some time, and Hosea is full of wit but he doesn't pretend to be an intellectual. So it's easier to admit he's found smarter than him.
In a completely different approach, Uncle critiques Dutch very upfront in a mocking manner.
"That's his problem, he wants to be an american king, with his knights"
To uncle it's very clear: Dutch reads and talks empty words. His words are not further from Lenny's, except that he's taking away the middle man (Miller). Dutch wants an equality where he still gets to be superior, and Dutch responds in a similar manner, he threatens Uncle as a joke.
Once again, Dutch gets upset, but not in a baffled manner like with Lenny, Uncle is not educated like him. Violence will not make him lesser, because a person that he perceives as less is deserving of violence.
I do think both characters believe in their philosophies, it makes them uncomfortable when they're presented with an opposing view from someone who they cannot dismiss easily. Dutch doubles down, Hosea deflects; both are complicit, but it would be a lie to pretend that Hosea's less prideful demeanour is what lets him be open to change. After all, he's the one to suggest change, but he doesn't take the opportunity, because he still deeply believes in their "cause".
