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TLKY & Daas Yochid,
Obviously there are people who call themselves “Orthodox” but are not really (I don’t mean to cast aspersions on Rabbi Druckman, I don’t know who he is). I should have qualified my statement with “a known, genuine Orthodox Rabbi.” If, however, the Rav is genuine, then we don’t inquire after the geirus but assume it is valid.
Rav Moshe writes that even in the cases such as you describe (what I called objectively insincere) it is at least a defensible position to be maikel b’dieved on the grounds that when they say the words of kabolas mitzvos any insincerity is dvarim sh’bilev. Even though Rav Moshe himself would not do such a geirus.
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Igros Moshe Yoreh Deah Chelek Aleph, No. 160
I have to think about your conning Christian scenario, because in that case he told someone (the Church) beforehand that he wasn’t sincere. I am not sure what the halacha would be in such a case.