Spoiler Talk below-
From what I gathered, in Flynn's route, we see the accidental death Sydney did to his father, giving context to the rumors Chase, TJ, and Carl know in TJ's route in their flashback scene: the rumor of him killing his father. So, a kid that bullied you and your friends now having talk that he killed his own dad stacked on top of all that?
This...did not look good for Sydney's reputation at the time along with how much of a dick he acted to the group in general with his roughhousing and bullying. So Chase was already wary of Sydney from the get-go once that secret was out.
In TJ's route, The day Chase saw Sydney mess with TJ at the beach with pulling him about in the water, he assumed the worst with intentions and He finally got fed up with Sydney's antics, thus leading to Chase killing him and the possession taking over him from that point onwards, changing him for the manipulator we see controlling TJ now in the present.
Now, whether or not it was from pure hatred or being controlled by the (socket man?) spirit when it appeared at the beach, I'm unclear of. Everyone disliked Sydney but Flynn. So I wouldn't doubt that Chase would go that far.