@_Meh_:
Ohh, the poor Tontatta! That bastard, Usopp! How dare you lie to them about being a hero, and then run away like that?! And you think coming back to tell them you lied will make up for it?!! You bastard!!!!
All of you who have felt these feelings welling up inside of you…
you have been deceived.
In spite of their cute appearances and dopey, friendly behavior the Tontatta took Usopp and Robin hostage, demanded that they hand over their weapons, and threatened to strip them and abandon them in the wilds of Green Bit if they did not comply with Tontattan militaristic demands. I'm not even making this crap up.
From the reader's viewpoint, it's been months since all that happened, so to us it's water under the bridge. To Usopp, it's been a matter of hours. Usoland was just a way to save his own ass that could conveniently save Robin, too. His priority has been, first and foremost, to his crew-not to some Lilliputian tribe of pervy scavengers living off of whatever they can steal or extort. Was the tale of their nine-hundred years of suffering terrible to hear? Yes, the Tontatta have been exploited terribly. Does this change the fact that they stole Zoro's stolen sword and threatened to give us readers some free Robin fanservice? No.
If Usopp is going through the same character development he had 12 + years ago, it probably has more to do with Oda reintroducing the character to a new generation of the same target demographic that One Piece is aimed at.
You know. . .that actualy never crossed my mind. It's true, though, that as friendly as the Tontattas are being portrayed, and as tragic as their background is, and as an overall bunch of cute, gullible good guys, the thing is, they DID kidnap Robin and Usopp and threatened to steal all their belongings. In fact, even after being at peace with Robin, tradition said she still should be robbed of everything she had. That's kinda creepy.
It's mostly that, by impersonating a hero, Usopp has received so much love and empathy from the dwarves that it doesn't seem like he still thinks of them as some kidnappers that he had to fool in order to get out of a sticky situation. But maybe he still had that in mind all this time and he never considered them "allies" in the first place? Maybe he never got into the operation at all because it was the result of being stuck in that situation that had nothing to do with their initial mission (the Caesar Exchange team)?
That's plausible, and a good way to see it. Still, the three-way Den Den Mushi conversation scene gave us Franky really empathising with the dearves plea, and Luffy gave permision to go all out to help them, so we could consider this as "captain's orders", and thus Usopp should've considered that his mission as a SH member from that point onwards, not something he's being somehow forced to do (by keeping that facade). I don't know anymore, honestly. . .