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shlishi; Your topic of discussion is a very interesting and wide ranging one; Generally. It is possible for someone who was involved in financial crimes, whether it’s armed robbery or crooked investment deals to do a complete T’shuva. But for someone like Bernie Madoff it is next to impossible to do T’shuva. As it says in the Mishna in Pirkei Avos ????? ?????? ??? ??????? ???? ????? ?????. That if someone causes others to sin, he does not get divine help to facilitate his repentance. The ??”? (Rabbeinu Ovadia of Bartenura) explains the reason for that. Because it would create an absurd situation where he would be considered atoned (for his sins) and those that he caused to sin would remain so (In the eyes of Hashem).