Mun Note: Seeing as I have mentioned bits of this at various points to the people who write with him ( @intolerablexsacrifice & @tidefated ) it occurs to me I should make an official notation of it all for them and the (3) other people I write with so that everyone has the same particulars xD;

Charles had a very stable upbringing – at least until he was kidnapped at the age of seven and taken to the docks where he would be sold to Albinus and made to work as a slave until he managed to escape at the age of twenty. His parents were not noble, but they did make a modest living as merchants and were particularly doting on their one and only child. Today, he has no recollection of them but a vague lullaby of his mother’s and an awareness his father always smelled distinctly of mint and tobacco. 

When he escaped, he survived for seven months in the jungle on his own, living off the land and picking off scouts and guards that got too close to his hunting grounds. The searches for him never ceased, and his ability to evade them was sure to run out sooner rather than later when Teach observed him and managed to lure the rather wild youth out. 

It was through a liberated slave who served under Teach that they were able to communicate, as at that point Charles only spoke in Papiamento – he understood English and Spanish perfectly well, but did not trust those who spoke it predominantly and viewed them as dangerous ( for good reason ) 

Ultimately convinced to join Teach, Charles gained a lot of his understanding on how to socialize with free peoples through his time under the esteemed pirate. He spent eight years under that man’s flag, and in that time Teach tamed a good deal of his wilder edges – molding him into a protege with expert and discerning hands. 

It was through Teach that Charles learned not only how to socialize properly, but also how to read and write – starting these lessons at the age of twenty-one, his rudimentary capabilities are remarkable when one considers how difficult these skills are too acquire past certain ages. Though Charles had begun some lessons prior to his kidnapping, it is uncertain how much of that was retained when he was being taught later in life. 

Though he can read, Charles is very slow and – when he has to read aloud – it is notable that he still appears to sound out the words, and to pause if he is uncertain. He will sound it out in his head until he remembers hearing the word, before pronouncing it – the longer the pause, the more complicated the word tends to be phonetically.  

Charles attributes the man he is today largely to Teach, which was why betraying him after eight years under his wing was not a choice he made lightly. Freedom for others like himself and a place where that freedom could be sustained permanently was something he aspired towards – and his sense of duty to his fellow slaves and those who were crippled by slavers and civilization was not a sentiment wholly shared by Teach, nor was the idea that a sustainable society could be created for such persons.  

Eleanor Guthrie was an educated and ambitious woman whose morals appeared to align with Charles’ own – and whose understanding of things like politics, diplomacy and maneuvering were traits he recognized as requirements he lacked for building such a thing himself. He was perfectly aware that she needed him in order to establish herself – he was also perfectly aware that he needed her to establish his goals. 

Betraying Teach was done not by a man besotted by a girl but rather by a man who made a logical choice – for while he certainly did love Eleanor, at that point he was also not unaware that she was manipulating him. So long as he too was gaining, there seemed to him little issue in a romance based on mutually aligned goals and uses. 

Eight years after this choice, Charles had by then committed himself so completely to Nassau and – by extension – to Eleanor’s ideas on how to make Nassau self-sustaining, that the idea of leaving her was anathema. If he gave up on her and on Nassau then what did he betray Teach for to begin with? Stubbornness was a very strong motivator to him, even when it became clear again and again that Eleanor saw him as a tool to be picked up and discarded at her convenience. 

Yet it is also due to this intimate awareness that Charles can be redirected, especially if there is a possibility to build something better without her – or to take part in something already established that is by very definition, exactly what he seeks. 

So TL;DR, Charles timeline is:

• 00-07: Normal, loving upbringing
  
• 07-20: Enslaved
• 20-21: Escaped / living wild / first months with Teach
• 20-28: Serving under Teach
• 28-35: Events prior to season one, starting with betraying Teach
• 36-38: Events of the show, up to his death