The following is a brief summary of some of thoughts said over by R' Frand on the upcoming holiday of Rosh Hashanah this evening. I have attempted to reproduce these vorts to the best of my ability. Any perceived inconsistency is the result of my efforts to transcribe the shiur and should not be attributed to R' Frand.
Rabbi Frand quoted from a Mishna on Rosh Hashanah 26 which states that the Shofar on Rosh Hashanah is comparable to the Shofar of Yovel. Rashi states that even though the Shofar of Yovel in unrelated to Tefillah and serves an entirely different purpose (as it is as a clarion for the release of Avadim), we learn the Mitzva of Shofar from Yovel.
R' Frand then asked a practical question - Yovel comes every 50 years and there is only one Shofar blast. Why would this be the source for the annual Shofar blowing on Rosh Hashanah - a day when we hear 100 sounds?
R' Frand answered that the blowing of Yovel is the root of the blowing of Shofar on Rosh Hashanah because it signifies that the world has turned over. The eved who had worked for 20 years is being released. The land which was purchased 47 years ago is now being returned to its ancestral family. And the Avadim who are being released are not merely sent away. When Rosh Hashanah comes they begin a ten day period of feasting and are given luxuries until the Shofar of Yovel when they are sent home with gifts for their families.
This is why the Shofar of Yovel serves as the paradigm for Rosh Hashanah - it is to show that we can have a new beginning with a sea change from where we were last year.
R' Frand remarked that this is why the Gemara mentions that Yosef was released from prison on Rosh Hashanah. Prison in that day was not a cinderblock building where inmates had three square meals, an exercise yard and TV. It was a hole in the ground or a cave with no running water. Yet Yosef who had been in prison for 12 years was released on Rosh Hashanah and taken to Pharaoh where he was able to eloquently interpret the dreams and was then placed in the position of second in command.
This is what Rosh Hashanah can signify and bring us, IYH. The Sfas Emes teaches that everyone can be released from his own personal master (Yetzer Harah) on Rosh Hashanah.
R' Frand said a second thought based on a Gemara in Bava Metzia. There is a halacha that if an Aris (sharecropper) is told to plant one crop and he chooses to plan another, he is responsible if the new crop does not produce the proper yield. Even if the entire area is flooded and all fields (including those owned by other people) are devastated, the owner of the field which was worked by the sharecropper can still be held responsible. Why? The Gemara states that the owner can say to him - I davened on Rosh Hashanah that my field would produce abundant wheat, but since you planted barley, it was flooded and destroyed.
Rashi quotes a pasuk in Iyov to explain this - what you ask Hashem for on Rosh Hashanah can be granted. The owner can say, I did not ask for this. Had I davened for the crop you planted, Hashem would have listened and the field would have been saved from the flood.
R' Frand said that this is a powerful lesson of what the davening on Rosh Hashanah can bring. As the Shulchan Aruch paskens that the sharecropper is responsible. IYH we should daven well on Rosh Hashanah and be granted yeshuos in the new year.
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