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Could chester have been with the order of Abyss Watchers, since they're the only other ones with a bloodborne-esc appearence, that and he knows who artorias is, which people seem to forget in ds3. He also doesnt make use of a shield, similarly to the abyss watchers.
You are of course forgetting Leonhard the Ring finger. He was a noble, evidenced by his knowledge in sorcery and his masque. Chester's attire is similar and if he was meant to attack alongside dogs, as a huntsman of sort, it fits all the more. The masque helps to suggest nobility as well.
His style of clothing Is most likely from the Victorian Era (1837-1901), instead of the Elizabethan Era (1558-1603). What stood out to me was all the knifes, daggers, and other small blades on his persons along with his bag—very similar to those used by doctors during the Victorian Era. My theory is that Chester is the infamous Jack the Ripper, as the serial killer showed the highly trained skill of a surgeon from his victims wounds. I personally enjoy this theory, and whenever I play, I believe it’s the truth. Thoughts?
headcanon =/= truth
Do you not know the definition of a “theory”? You must be fun at parties.
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Atikah

Joined: Fri Dec 28, 2018 10:06 pm
Souls: 50.00
Posts: 10
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The jack the ripper thing jumped the shark, but the rest, a Victorian physician from a Dark souls 19th century is a great way to imagine him.
I got his set without killing him? Dark Souls Remastered. Playing coop (as host obviously). Found him, exhausted dialogue. Took the path leading down. Died to Dragon. Talked to Mushroom Elizabeth. Was summed to coop, we did the same thing, died to dragon. Hosting again, went through shortcut, Chester was standing with his crossbow in hand, non-aggressive, but wouldn't let me interact with him. At his feet, his gear. Anyone else ran into this? I was cooping with my brother, we could not replicate this.
Have not finished the DLC yet, have only killed Artorias so not sure if this is "normal", but after killing Artorias, I went back to his location and he was gone.
I guess Chester could have been an early Workshop hunter (circa the Gehrman/Maria era) but I seriously doubt there's any canonical relationship between the two games (both for Chester and in general). I'm just glad there's no ridiculous Rakuyo speculation here (GWYNDOLIN *IS* MOON PRESENCE GUYS)