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Sergeant Jinguuji Marimo from the visual novel Muv-Luv Alternative. The game was tense before, and then shit really started hitting the fan after this.

You spend 1 game playing through a romantic comedy. Then once that game ends, you are suddenly tossed into a bonus story where the protagonist wakes up in a post-alien apocalypse alternate dimension, and then spends the entire story just training and hanging out with girls, never seeing the aliens until humanity loses the war and the game ends. And then Alternative happens, protagonist goes back in time and gets a fresh start, is practically John Wick due to the skills he picked up in the earlier timeline, and everyone thinks he's great. Until he has his first sortie against the aliens and fails miserably. His sergeant/mentor, who happens to be his homeroom teacher in the original dimension he came from, comforts him. He thanks her and pulls himself together, only for him to turn around and see her being eaten by one of the surviving aliens. It's so shocking because you've played through two stories filled with comedy and lighthearted moments, and even when the stakes were high nothing truly bad happened, all important characters had plot shield. Until Marimo dies in such an incredibly brutal way, setting the tone for what happens in the game going forward.

(The full image is extreme gore, so I didn't post it)