Hoshana Rabba
After all the tefilos on Rosh Hashana and Yom Kippur, we hope to have earned a good year. Yet just a few days later, we spend one more day immersed in davening, crying out again and again, hoshana, please help us. What are we trying to accomplish that we have not already achieved?
The Gemara (Bava Metzia 85a) tells of a calf that was being led to the slaughterhouse when it broke loose and ran to the Tanna Rebbi Hakadosh, trying to hide under his jacket. He handed it back to its owners, saying, "Go! This is what you were created for." Because of this single instance where he showed a lack of compassion, Rebbi endured years of suffering.
Many meforshim question the justice in this story. What did Rebbi do wrong? He was absolutely correct – Hashem created animals for the express purpose of serving Man, including as a source of food. Why should he have shown mercy?
My Father, Rav Noach Isaac Oelbaum Shlita, suggests that this Gemara illustrates an important principle. We are meant to develop our rachmanus and become compassionate people. This is so important that it overrides the usual purpose of Creation. Even if someone deserves a certain fate, if they cry out and beg for mercy, this alone is sufficient reason to change direction and spare them. When the animal came to Rebbi and begged for its life, he should have shown compassion and saved it, despite any other factors.
We leave the Yomim Noraim uncertain as to our fate. Perhaps we are deserving of punishment for our various transgressions. Therefore, we spend an entire day pleading with Hashem, hoshana, please save us from any harsh decrees. This can arouse the midas harachamim, even if we are not truly deserving.
Retzon yerei'av ya'ase, v'es shavasam yishma v'yoshi'eim. Hashem fulfills the desires of those who fear Him, and He hears their cries and saves them. The Hafla'ah, in his sefer Panim Yafos, explains that we ask Hashem for help, but He knows that many of these wishes are not for our ultimate good. However, He does not want to disappoint those who are close to Him. Therefore, retzon yerei'av ya'ase He might grant their request, knowing that there will be unintended consequences. Later, when the person realizes his mistake, he will cry out to Hashem for help, and Ve's shavasam yishma v'yoshi'eim, He will help him, even though he brought the situation upon himself. This is the power of a Yid's cry. Even though it might be undeserved, even though he caused the problem, Hashem will answer a sincere plea.