On Rosh HaShana, there is a custom to eat the head of a sheep or the head of a fish after reciting the following blessing: May it be Your will, HaShem, our God and the God of our forefathers, that we be as the head and not the tail.
The blessing comes from Parshat Ki Tavo, Devarim 28:13: “God will place you at the head, not at the tail; and you will be solely on top, you will not be on the bottom; when you heed the commandments of HaShem your God, that I am commanding you today to guard and to perform.”
According to Ramban, God will make you the head of all peoples and not the tail of any one of the nations. He will henceforth make you the head and at no time will you ever be the tail.
The Apter Rav, Rabbi Abraham Joshua Heschel (1748-1825) of Zmigrod, Poland, author of Ohev Yisrael asks why the blessing needs to be stated positively and negatively. Why doesn’t it just say “at the head”, why does “not at the tail” also need to be included?
Doesn’t Rabbi Yanai teach us in Pirkei Avot 4:15 that we should be the tail: “Be a tail unto lions and be not a head unto foxes”?
Rabbi Heschel answers: “at the head”- you should be the “head” of the “head”, “not at the tail”- you should not be the “head” of the “tail”. You should be the head of the lions, not the head of the foxes.
As we prepare for Rosh HaShana, we should continue to strive to be the best that we can be and not settle for mediocrity.
For those of you who are not comfortable eating the head of a sheep or the head of a fish you can follow Rabbi Jonny Gordon and eat the heads of gummy fish!