Q. Why do we read the same Torah over and over again every single year?
He said that as far as he was concerned, reading the same Torah passages inspired him to study the material each year through the eyes of a different commentator. This year it might be Rashi, next year Ramban, then Ibn Ezra and so on.
There is so much rabbinic literature that one is not likely to run out of commentators, but one can always go back and find new insights in the commentators one looked at in the past.
A Chassidic rebbe had a slightly different approach, though in his case the question that he was answering was rather different.
He was asked about the confession of sins on Yom Kippur.
Why, said the questioner, do I beat my breast every Yom Kippur and confess my sins, and end up committing the same sins all over again the following year?
The rebbe took the questioner over to the window.
“Do you see the little child playing in the garden?” he asked.
“He is my grandson. He is just learning to walk. He stands up and then falls over. Finally he will learn how to stand up properly and how to walk without falling. In the meantime he cries and his parents come running. Eventually he will manage on his own!”
So it is with us. Every year we read the same Torah. We discover how to live our lives. In time we succeed in living by the laws of justice, truth and humanity.
In the meantime we need the annual reminder, and when we cry out to God He comes to our aid.