Hey cheesecicles! So I didn't make the actual headcanon, but I did come up with boggarts for most of the characters!
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In case your confused, a boggart is a thing from Harry Potter which is basically a person's worst fear/reality.
So, here we go!
Leo's boggart is his brothers being dragged away by the enemy as the other turtles yell about how he's failed them and that he's a horrible leader and he's powerless to stop them.
Raph's boggart is a giant cockroach trying to eat him as a lot of little cockroaches crawl all over his body.
Donnie's boggart is April telling him how much she hates him and that no one could ever love him because he's a gap-toothed, pale freak. That and one of his inventions blowing up and killing his whole family.
Mikey's boggart is the pizza faces, parasitic wasps and squirrelenoids attacking him as they eat the last of the pizza in front of him and attack and kill his family and friends.
Splinter's boggart is the Shredder standing over him, raising his gauntlet as he lies by the slain bodies of the turtles, Tang Shen and Miwa as the building they are in is burning and slowly collapses upon them.
April's boggart is her father in his mutated bat form looking at her like he wants to eat her.
Casey's boggart is rats climbing all over his body and attacking him as a giant one eats him.
Karai's boggart is the Shredder standing over her telling her that he killed her mother and that he wished she had burned like her as the building they are in is engulfed in flames.
Kirby's boggart is April dissappearing and being murdered/kidnapped by the mom-thing as the mom-thing grabs him, looking him dead in the eyes, telling him that he should remember her as her body morphs into something horrifying.
Usagi's boggart (I know he's not a major character but I like his character) is watching his master get decapitated right in front of him once again as Jei was standing above him, holding Akemi and Kintato hostage as he murders them in front of him.