Digimon Adventure 02 #9 - Overdrive of the Evil Ring's Magic 

In characterizing Ken the story's been showing off his rationale for attempting to assert power wherever he can while also demonstrating for the audience that those reasons are wrong; every cruel action of his seems to be the result of his overinflated ego and insistence on self-isolation. A lesser show would've made it a "cycle of cruelty" deal with abusive parents, but every aspect of his life seems perfectly supportive at this point

Digimon Adventure 02 #21 - Goodbye, Ken-chan... 

I appreciate that this show for young children is willing to spell out that someone with all the practical knowledge in the world is nevertheless capable of adopting a fascist mindset and creating mass destruction given the means and the rationale that his targets aren't 'alive'. The metaphor would've been better executed in a setting not constructed to sell a (very much not alive) virtual pet you can buy in stores, though

Digimon Adventure 02 #21 - Goodbye, Ken-chan... 

This and the episode where Hikari gets abducted by horrifying sea creatures are immediately preceded or followed by extremely light episodes; every In the Pale Moonlight gets its own His Way

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