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WM: Have you ever c’v had to say Kaddish for someone halachicly required of you?
Yes. My mother passed away five and a half years ago.
If not, are you even allowed to say Kaddish for someone not halachicly required of you?
Question not applicable since the premise is not true.
If you c’v had to say Kaddish for someone halachicly required, would you be asking the same question you ask in your OP? Why would it be less applicable?
Because halacha says that you are required to say kaddish for some people, and we find no exception that says that one is exempt if one is wicked. However, perhaps, if not required, one should not say it, so as to not harm the deceased.
The Wolf