Fill is just a one-shot (the real story begins with Haytham Lee), but yes, Connor slowly wins himself more and more freedoms. Not quickly, not well sometimes either, but he does learn the art of using compromise and giving to get what he desires more in return.
...also, this negotiation only worked here 'cause Charles doesn't really want to break his word to his wife. By finding a way to make the results to Charles, Connor has forwarded his own cause (not having his people's land stolen, which Charles was expecting) and also finagled his ability to see his childhood friends and tribe (which totally slipped past Charles, lol!).
Re: Continuing Fill 2 - A Loyal Wife
...also, this negotiation only worked here 'cause Charles doesn't really want to break his word to his wife. By finding a way to make the results to Charles, Connor has forwarded his own cause (not having his people's land stolen, which Charles was expecting) and also finagled his ability to see his childhood friends and tribe (which totally slipped past Charles, lol!).