This matchup idea is even more phenomenal than
Sayori VS Ned Leeds.
I feel like Basil would win this matchup. My premise is that Basil is more mentally unstable than Sayori and Sayori is more gentile than Basil, therefore Basil is more likely to fight and win in this situation where it is mandatory to fight even though the characters wouldn't be likely to fight in the situation.
Warning; I will be analyzing the cognitions of the characters, which includes their overwhelming feelings of self-loathe, so brace yourself if you want to read further.
Although Basil is generally timid, he is more prone to using violence since he's done that twice before,
once as a kid to help Sunny avoid trouble by framing Mari's murder as a suicide, and
once as a teenager where he had a mental breakdown trying to get rid of Something (the manifestation of his guilt/trauma) by attacking Sunny.
Another instance shows Basil having a non-violent breakdown after he found out that Sunny was moving out of town, further demonstrating that it's common for Basil to be unhinged.
Basil is also used to being bullied by Aubrey before
a misunderstanding was cleared up, so he is likely to be on guard in public.
His sadness can lead him to killing himself. Something may have been around Basil when it happened, but that character is supposed to be a personification of negative emotions, not a corrupting force beyond the characters. Although Basil doesn't have his gardening shears, he could find something in the hallway like a pen to use as a weapon, especially since him being good at gardening means he is probably good with his hands to some extent in this way. Sayori may be more physically mature than Basil, but that isn't useful when she hasn't shown any useful physical conflict knowledge at all. Sayori is a kindhearted sweetie who
prefers to settle conflict with positivity, and the most combat experience she's been shown to have is
getting smacked in the face with a cookie in a safe social interaction. She's just a normal slightly clumsy schoolgirl, so she would be too unprepared to engage in combat in an effective way. She doesn't normally have violence on her mind. As shown in
two conversations with the protagonist, her depression doesn't seem to stem from any sort of event that caused it, and the effects are that she feels downcast which she hides, and that she feels internally conflicted due to having simultaneous feelings of selfishness and emotional deprivation, causing some sort of aching. Also, Sayori didn't independently kill herself, so her urge for violence is more difficult to emerge than Basil's. Monika
was implied to have recommended that Sayori should kill herself, and the reason Sayori went through with the plan was because
Monika supernaturally edited Sayori to amplify her negative trait in an attempt to get rid of her.
It's unfortunate for Sayori to lose, but I feel like the battle would simply be Sayori ineptly blocking Basil's inept attacks, until Sayori would lose. Sayori would at best try to push Basil off of her, but Basil could potentially use an object in the location to help him win faster, while Sayori probably wouldn't think of that nor be familiar with using an object to fight. If both combatants are completely in character, then neither of them would fight, but since they can't simply stop fighting due to
Standard Battle Assumptions which also dictates that the characters see each other as enemies and will attempt to win the battle, we need to determine which character is more likely to fight, and I think that character is Basil for the reasons explained in the previous paragraph. I vote for Basil to win.
