When I first knew him your father was already a great pilot. But I was amazed on how strong the force was with him. I took it upon myself to train him as a Jedi. I though that perhaps I could instruct him just as Yoda, I was wrong.
~ Obi-Wan Kenobi on how Anakin Skywalker betrayed him.
You're the one who doesn't get it, Cozy. Friendship is powerful, but power isn't why you make friends. I'm sorry I couldn't teach you that.
~ Twilight Sparkle to Cozy Glow.
I... I have always been proud of you. From the first... moment I've been... proud of you. And it was my pride... that blinded me. I loved you too much to see what you were becoming. What I... was turning you into. I'm... I'm sorry.
~ Shifu apologizing to Tai Lung for failing him as a teacher.

Heroes who are masters and have students/servants/apprentices/disciples who have become villains. The direct opposite of Master of a Hero, for villains who trained students who would become heroes. Most of the time this is caused by betrayal, either due to a corrupting influence or the teacher failing them as a master. Some of these heroes are likely to be naive and therefore not know that the villains who serve them are actually plotting to usurp or betray them, as is the case with Korosensei. In some cases this may overlap with Friend of a Villain if a hero wants to make things right or still feels a connection with their fallen pupil, or even succeed in redeeming them. Famous examples include Batman, Luke Skywalker, Kakashi Hatake, Sensei Wu, Albus Dumbledore, Megamind, Hank Pym, and many others.

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