Prayer is always an avenue to God. But in the month of Elul, the last month of the Jewish year, and during the ten days between Rosh Hashanah and Yom Kippur, God lends a particularly sympathetic ear.

And so when Moses trudged despondently up the mountain that first day of Elul, after dashing the tablets of the Law, and for forty days and forty nights begged God’s forgiveness, the sin of the golden calf was forgiven. On that Yom Kippur, the shattered pieces of God’s faith in the Jews was restored and the twin tablets of their eternal relationship renewed. And ever since, these forty days between Rosh Chodesh Elul and Yom Kippur have been prime time for prayer.

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The romance in this prayer date is picked up in midrashic literature. The Midrash points out that the first letters of each word of the verse “Ani ledodi vedodi li” – “I am my beloved’s and my beloved’s is mine” – spell out the word Elul. So too the first letters of the verse “Ve’asher lo tzada velokim ina le’yado vesamti lecha makom” – “if he did not plan to kill his victim, but God caused it to happen” – referring to the cities of refuge for manslaughter, spell out Elul. For Elul too is a safe harbor in time, during which God protects us from the damaging consequences of our sins.

Similarly, the first letter of each word of the verse “Ish le’reehu umatanot la’avionim” –“sending choice portions to one another and gifts to the poor” – which emphasizes the role of charity in procuring God’s forgiveness, also spell out Elul.

When Moses ascended the mountain that first, fateful day of Elul, the shofar was sounded daily in the camp of Israel, heralding his expected return. This eliminated the possibility of the disastrous conclusion, previously drawn from his prolonged absence, which resulted in the sin of the golden calf. This is the source of the rabbinical requirement that we sound the shofar each day of Elul. The shofar awakens us and admonishes us not to slumber thorough this unique period of communication with God.

Commencing with the first day of Elul, through Rosh Hashanah and Yom Kippur and culminating on the last day of Sukkot, we recite Psalm 27 – “The Lord is my light and salvation” – after each morning and evening prayer service. The focal point of reference therein is to the word “light,” denoting the spotlight of judgment trained upon us on Rosh Hashanah, as well as to the word “salvation.” denoting God’s outstretched Hand of Salvation on Yom Kippur. The Psalm also reminds us of God’s protective roof on Sukkot.

If repentance is not to be used merely as a credit card to postpone payment at maturity date, then we must endeavor to sincerely honor our commitment and repent before the Day of Judgment. This concept is alluded to in the words “Lo yachel de’varo” – “if a man makes an oath to obligate himself, he must not break his word.” The last letter of each of these words spell out Elul. But just in case, despite our sincere endeavors, we fail to meet such commitment before Rosh Hashanah, God does grant us an extension. Accordingly, it is our custom to annul our vows on the last day of Elul.

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Raphael Grunfeld received semicha in Yoreh Yoreh from Mesivtha Tifereth Jerusalem of America and in Yadin Yadin from Maran Hagaon Harav Dovid Feinstein, Shlitah. A partner at the Wall Street law firm of Carter Ledyard & Milburn LLP, where he specializes in cross-border mergers and acquisitions, Raphael is the author of “Ner Eyal, a Guide to Seder Nashim, Nezikin, Kodashim, Taharot and Zerayim” (2016) and “Ner Eyal, a Guide to the Laws of Shabbat and Festivals in Seder Moed” (2001), both of which are available for purchase at https://www.amazon.com/dp/057816731X Questions for the author can be sent to rafegrunfeld@gmail.com