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I'm pretty sure Kiritsugu was making excuses to himself, bringing up Sherry since it was his mistake to not kill her there and then that caused that tragedy on the island. We get to see earlier in the episode that he already linked this case with what happened with last weeks episode, so I don't think it was a bad way IMO.
Also, by the time he broke down and started crying, he was more of cursing himself for what what he had done ...
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