To understand Rashi's literal intention, we begin with the pasuk (17:5) ...ההיא האשה את או ההוא האיש את והוצאת וסקלתם ...שעריך אל, "You shall take that man or that woman out... to your gate... and you shall pelt them with stones..."
It discusses the punishment for those who worship avodah zarah and states that they are punished at the gate. But the pasuk doesn't state which gate. Is it the gate of the beis din where they were judged or the gate of the city where they committed the aveirah? Onkelos says דינך בית לתרע, the gate of beis din. Rashi disagrees. He says בו שעבד שער that they are punished at the gate of the city where they committed the aveirah. Rashi adds, טועה דינך בית לתרע שעריך אל המתרגם, Those who translate that they are brought to the gate of the beis din are making a mistake." It isn't the gate of the beis din instead it is the gate of the city.
Kol Yaakov (written by Reb Yaakov Rokach zt'l, from the gaonim of Tripoli, about two hundred years ago) writes several hints for the word ל"אלו. One is (Tehillim 106:46) לפני לרחמים אתם ויתן, the roshei teivos are אלול. This hints that they will receive rachmanus. The following words are שוביהם כל, for all those who do teshuvah. (2) (Tehillim 27:8) לבי אמר לך וענני is roshei teivos ל"אלו. That Hashem will answer us in chodesh Elul. (3) (Tehillim 68:21) ולאלקים למושעות ל"א לנו, is roshei teivos ל"אלו, and it tells us that there will be yeshuos in this month. (4) (Tehillim 35:23) לריבי י"ואדנ אלקי למשפטי והקיצה העירה, is roshei teivos ל"אלו and hints that one should awaken from his slumber in this month. (5) (Tehillim 73:26) לעולם אלקים וחלקי לבבי is roshei teivos ל"אלו.
It states (Devarim 21:13) ימים ירח אמה ואת אביה את ובכתה, "She shall weep for her father and her mother for a full month." The Zohar (Chadash 72.) says, דאלול ירחא הוא דא ימים ירח, the month referenced is the month of Elul. This hints to the need to do teshuvah in Elul, and to cry over our misdeeds. Mishnas Chasidim (מחשבות חושב parashas Ki Seitzei) explains that the pasuk doesn't state ימים חדש, rather ימים ירח, because ירח is roshei teivos חודש ראש יום. To hint that from rosh chodesh Elul onwards, a person should begin his teshuvah. He shouldn't wait until the middle of the month.
Or Pnei Moshe (Va’eschanan בדברי ה"ד) explains the Midrash (Devarim Rabba 7:10) that when Moshe said to Hakadosh Baruch Hu (Devarim 3:25) הטובה הארץ את ואראה נא אעברה, "Let me now cross and see the good land." Hakadosh Baruch Hu replied, "If it is נא אעברה that you request, then it will be mevatel (annul) the נא סלח (Bamidbar 14:19), and if you ask for נא סלח, then it will be mevatel the נא אעברה." We can explain that א"נ alludes to the 51 days from rosh chodesh Elul until Simchas Torah. The reshaim say א"נ אעברה, let the 51 days pass. They don't have patience for these days. (The end of the pasuk explains why they don't like these days. As it states ואראה הטובה הארץ את, they want to enjoy the pleasures of this world.) But if it is so, and they don't take advantage of these days of teshuvah, then they will lose the נא סלח, the atonement of Rosh Hashanah and Yom Kippur. However, if a person wants נא סלח, to be forgiven for his aveiros on these days, then he should make sure not to אעברה א"נ, that these 51 days shouldn't pass without utilizing them for teshuvah and tefillah.
About parashas ראה, which is read either on rosh chodesh Elul or on Shabbos Mevarchim Elul, the Beis Aharon zt'l said that ה"רא is roshei teivos of הולך אלול ראה, "See that Elul is going." One can ask, why didn't the Beis Aharon say that ראה is roshei teivos for הגיע הולך ראה, "See that Elul arrived." Why did he choose the word הולך, that it is going?
We can answer this question with a lesson from the Baal Shem Tov: Friday night before Shemonah Esrei, we say וינפש שבת השביעי וביום, and Chazal (Beitzah 16.) say that these words mean שבת השביעי וביום, when the seventh day ends, נפש-וי, woe, the nefesh has left (נפש אבדה וי). Because after Shabbos leaves, people moan that they lost their neshamah yeseirah. The Baal Shem Tov zt'l asks why we say these words at the beginning of Shabbos. A more appropriate place would be at the end of Shabbos because that is when people moan that the neshamah yeseirah has left them.
The Baal Shem Tov answers that when Shabbos arrives, we are reminded that Shabbos will soon leave, and then we will regret that we didn't make better use of the Shabbos. Soon you will say נפש אבדה וי, "Woe, the nefesh yeseirah has left me." Remember this at the beginning of Shabbos, and you will utilize your time wisely.
We can say that this is also why the Beis Aharon linked the word ראה to הולך אלול ראה, remember that Elul is leaving. In just thirty days, Elul will be over. Remember that at the beginning of the month, and you will use the month wisely.
The Beis Yisrael zt'l (5717, שופטים ה"ד) brings a Rashi (17:5) that says, טועה דינך בית לתרע, "The gate of beis din is making an error." The Beis Yisrael says that alluded in these words are a lesson in teshuvah. Rashi is saying that those who do teshuvah at the gate of the beis din, which means they begin doing teshuvah in Tishrei when we stand in judgment on Rosh Hashanah and Yom Kippur, טועה, these people are making a mistake, because it is very late to begin doing teshuvah then. Rashi writes that the correct way is בו שעבד שער, "the gate where he committed the aveirah." This means our teshuvah should begin immediately after we commit the aveirah. And if we didn't do teshuvah then, at least we should do teshuvah in Elul and not wait for the last minute.
If a person had a court case, would he begin preparing for it a moment before he goes to court, or would he prepare days in advance? This is why we have Elul, to prepare ourselves with teshuvah to merit good judgment.
The Midrash (Hoshea 14) says, עד ישראל שובה אלקיך 'ה, that one should do teshuvah when it is still days of compassion, and the Chasam Sofer (Drashos, Drush for parashas Netzavim, 5595) says that this means he should do teshuvah in Elul, which are days of rachamim before the days of din and judgment arrive.
Three people came to the Divrei Chaim of Sanz, zt'l. The first one cried, "Rebbe, it is Elul, and I want to do teshuvah." The Rebbe said, "If you want to do teshuvah, do so! Why did you come to me?" He didn't want to speak to him. The second person also told the Divrei Chaim that he wanted to do teshuvah, and the Divrei Chaim gave the same answer. The third person came to the Divrei Chaim of Sanz zt”l and cried and said, "Rebbe! Elul has arrived, and I still don't even want to do teshuvah." The Divrei Chaim accepted him and taught him the path of teshuvah. This is the avodah of these days, to reveal the desire to do teshuvah.
The Divrei Chaim concludes one of his teshuvos (Shu"t Divrei Chaim Yorah Deiah vol.1, 33), "To just be mifalpel in learning (to write in-depth, clever ideas in Torah), this isn't a good time for that, because we have to check the depths of the heart during these awesome days. Signed, Elul, 5617..."
The Sfas Emes said to one of his wealthy chasidim, "All year round, I speak to you about your business (because the Sfas Emes would advise him regarding his business). But during this month, the best investment is to invest in teshuvah." When one invests in teshuvah in this month, he earns great benefits, b'ruchniyus and b'gashmiyus, for the entire upcoming year.
The Sfas Emes writes in a letter (year 5625, Likutim), "My dear friend, rosh chodesh Elul isn’t the right time to sleep in the dormant of this world. It is certain that these days, heaven arouses people to do teshuvah, but a person has to do his part, too.
The Ohev Yisrael (the Apte Rav zt'l, Re'eh, עשר ה"ד) writes, "It is known from the holy sefarim that Elul is the time for a person to check the deeds he does throughout the year and to correct them with charatah (regret), viduy (verbally admitting the aveiros), and with teshuvah sheleimah... and with kabbalah l'asid, to accept on himself that from now on he will attach himself to fear Hashem all day long. We can explain the reasons why specifically Elul was chosen for this introspection. One reason is so every Yid will come to the day of judgment, Rosh Hashanah and Yom Kippur, clean from aveiros. Another reason is that אלול spells א לול. A לול is a window (see Zevachim 55:). ל"אלו hints to us that in this month, a window is opened to accept those who do teshuvah with truth." It is easier to do teshuvah in Elul. A window opens in heaven to accept our teshuvah. And this is particularly needed for us this time of year so that we can come to the holy days of judgment clean from aveiros.
The Arvei Nachal (Shabbos Shuvah 4) writes, "Throughout the year, when a person does an aveirah and he doesn't do teshuvah, he has only one aveirah, the aveirah that he performed. The fact that he didn't do teshuvah isn't considered an aveirah. This applies all year round. However, starting from rosh chodesh Elul, which are days of ratzon [a time when our teshuvah is accepted with love], if these days pass and he doesn't correct himself [with teshuvah], he now has to do teshuvah on two matters, because now he has two aveiros. One aveirah is the aveirah he performed, and the second aveirah is that he didn't do teshuvah. This is the meaning of the pasuk that states (Bereishis 43:4) פעמיים זה שבנו עתה כי התמהמנו לולא כי. i[לולא has the letters of אלול, and התמהמנו means to wait.] התמהמנו לולא כי, if he waits and he doesn't do teshuvah during Elul, פעמיים זה שבנו עתה כי, now he has to do teshuvah on two aveiros."
Or Pnei Moshe writes, "It is known that in Elul, with teshuvah, one fixes the aveiros he performed throughout the year. Perhaps this is the meaning of the pasuk (Devarim 32:5) מומם בניו לא לו שחת, "Corruption is not His – the blemish is His children's." The words לא לו spell אלול, backwards. [The combination of לו לא and אלול] means that they don't do teshuvah, not even in Elul. Then בניו, the madreigah that they could have been called "Hashem's children," מומם, is lacking from them." It is a beautiful level to be called "Hashem's child." We get that title when we utilize these special Elul days. Because these days are mesugal for teshuvah, to become close to Hashem with love, לי ודודי לדודי אני, like a son coming near to his father. But if one doesn't take advantage of this time, this closeness will be missing, and he won't be called "son," as implied in the words מומם בניו.
Or Pnei Moshe continues that, therefore, we say on Rosh Hashanah, כרחם רחמנו כבנים אם בנים על אב, that if we did teshuvah in Elul and are considered Hashem's children, then Hashem should have compassion on us like a father has compassion on his children.
