Everybody asks the question, why is the teffilah of a tzadik ben tzadik greater? We would have thought that the tzadik ben rasha should have a greater teffilah since Chazal say that even perfect tzaddikim are unable to stand where baalei teshuva stand. There is a famous answer from Rav Chaim Shmuelevitz that for the tzadik ben rasha it is inherent that he will have his own unique personal connection to his avodas Hashem since, after all, he had to swim against the tide to get to where he is. The tzadik ben tzadik, on the other hand, lives with the difficulty of finding his own approach. When a tzadik ben tzadik overcomes the natural tendency of simplistic imitation and instead carves his own niche, his own new unique approach – both in terms of his understanding of Torah as well as in avodas Hashem; everything should be alibah dideih – that is a supreme accomplishment that makes his teffilah more effective.
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