Episode 6: Kidnapping Kalinka Cossack to frame Mega Man, then shackling her to an ion bomb when he intervened.
Episode 7: Torturing an innocent Metool by way of a direct pain program, and considering using it on ProtoMan.
Episode 8: Talking about wiping the female robot master's memory within earshot of her and ordering Drill Man on a suicide mission. This proves atrocious enough to make Drill Man pull a Heel–Face Turn.
Episode 10: Giving a direct order for the Mega Man Killers to kill Kalinka right in front of Mega Man, in as painful a way as possible. When that fails, he forcibly takes control of the Ballade Crackers and detonates them right before Ballade's self-sacrifice.
Episode 10 epilogue (Major spoiler!): Torturing ProtoMan in cold blood after interrogating him, with a much more potent version of the pain program mentioned above. For hours. All because ProtoMan refused to fight Mega Man once due to an injured girl who needed help. And, as revealed later in Episode 11, he also removed ProtoMan's positive traits.
Episode 11: Forcing ProtoMan to verbally assault, betray, and vent against Mega Man during what was supposed to be a peaceful conversation, shattering their shaky familial bond. Then, in the climax, he orders ProtoMan to kill Mega Man with the Mad Grinder, and reinstills the fear program in him so he won't rebel.
The Stardroids crossed it in a flashback by destroying a planet in front of Duo, stalling him long enough to make him watch.