In the name of Rebbe Tzaddok HaKohen, "We don't know who the malachim are, and we don't know the essence of the Kisei HaKavod (Hashem's throne) either, but we know that the malachim are around Hashem's Kisei Hakavod, and on Yom Kippur, Hashem brings down His Kisei Hakavod to us. So, on Yom Kippur, we are around Hashem, as it states (Vayikra 16:30) תטהרו 'ה לפני, "Before Hashem, you will be purified." On this day, we become pure like the malachim in heaven.
The Chasam Sofer (Drashos vol.2, 369) writes, "The fast of Yom Kippur isn't to afflict us, and to cause tzaar to Yisrael, chalilah. Instead, it is because of the kedushah we have on this day, similar to the malachim [who don't eat or drink]. It is like the forty days... that Moshe was on Har Sinai, לא לחם שתה לא מים אכל , he didn't eat bread, he didn't drink water, because of his deveikus and the kedushah. This is our portion on Yom Kippur, when we become like the malachim, and we derive pleasure from the shine of the Shechinah.
The Chasam Sofer (Drashos vol.1 p.16) proves that even people's bodies become holy on Yom Kippur. The Gemara (Yoma 82) states that if a pregnant woman smells food on Yom Kippur, and she feels that if she doesn't eat it, her life is in danger, you can give her to eat that food on Yom Kippur. However, first, someone should whisper into her ears that it is Yom Kippur. Perhaps this will enable her to overcome her temptation, and she won't need to eat. But if she doesn't calm down after this message, one can feed her on Yom Kippur, because it is a matter of life and death.
This halachah, that one should whisper to the woman the prohibition, is only said regarding the prohibition of eating on Yom Kippur. Whereas, for example, if a pregnant woman smells and desires to eat non-kosher food, and she feels that her life is in danger if she doesn't eat it, the halachah is that you give her to taste the food. No one whispers to her that the food is prohibited. The Chasam Sofer explains that a child in a woman's womb has a very great kedushah. Chazal say that the child learns Torah from a malach! The Chasam Sofer writes, "If he weren't within the impure human body of his mother, the child would be greater than the malachim." But the human body, in this world, is very low, and it draws people to temptations. The Chasam Sofer explains that throughout the year, it won't help to whisper to the woman that the food is forbidden. However, on Yom Kippur, the mother attains purity, her body becomes pure, and now it is possible that she will be able to overcome the temptation and refrain when she is reminded that it is Yom Kippur.
At every tefillah on Yom Kippur, we say kedushah כתר, and not נקדישך. Mateh Moshe (ב"תתע אות) explains that on Yom Kippur, the Kisei Hakavod goes up to such a high place that the malachim aren't able to reach it. Therefore, we say כתר, which states in it איה כבודו מקום , "Where is Hashem's honorable place?" The malachim ask, "Where is Hashem's place?" because they can't find it; it is so high. This is unlike the kedushah of נקדישך, where the malachim say, ממקומך, "From Your place..." which implies that they know the place. This is the reason on Yom Kippur, we say Kedushah of Keser, and in it we say ממקומו, "From His place," wherever it is.
Shir HaShirim (3:11) writes, לּוֹ שֶׁעִטְּרָה בָּעֲטָרָה אִמּוֹ , "upon the crown with which his mother crowned him." The Gemara (Taanis 26b, Rashi ה"ד תורה מתן זה) states הכפורים יום זו אמו לו שעטרה, this pasuk, discussing a crown, is referring to Yom Kippur.
The Be'er Mayim Chaim (Naso הכהן ולקח ה"ד) explains a deep, amazing concept, based on this Chazal. He tells a mashal of a father who loves his child so, he lifts his child to his height. Sometimes, he will even raise the child above his head, and the child becomes like his crown. He does this because of his love for his child. This is a mashal to the high level that Hashem raises Bnei Yisrael on Yom Kippur. Hashem loves us so much, keviyachol, He places us like a crown on His head. This is the meaning of יום זו אמו לו שעטרה הכפורים , that Hashem purifies us and raises up to this high level on Yom Kippur.
The Be'er Mayim Chaim also bases this lesson on a Midrash (Shir HaShiri 3:2), which tells about a king who loved his daughter so much that he would call her בתי, "My daughter." He wasn't satisfied with this title; he wanted to express his love to her even more, so he began calling her אחותי, 'My sister." He still wasn't satisfied. These titles weren't bringing out the love he had for his daughter. Then he began calling his daughter, אמי, "My mother." "My mother" is the highest expression of love, and this is the meaning of the pasuk אמו לו שעטרה, that Hashem loves us so much, He calls us His mother, and Klal Yisrael are like a crown on His head. This significant level and expression of love occurs on Yom Kippur.
The Tur (606, quoting Pirkei d'Reb Eliezer) writes, "The Satan sees that there are no sins among the Jewish nation on Yom Kippur and says, 'Master of the world, You have a nation on earth that resembles the malachim in heaven. Just as malachim go barefoot, so do the Jewish people on Yom Kippur. Malachim do not have knees; similarly, the Jewish nation stands erect throughout the day. Malachim are pure from all transgressions, as is the Jewish nation on Yom Kippur. Among the angels, there is peace, and likewise, there is peace among the Jewish nation, as they seek forgiveness from one another before this day.' Hakadosh Baruch Hu accepts the Satan's testimony and forgives their sins."
The Midrash (Devarim Rabba 2:36) states that when Moshe was in heaven, he heard the malachim say ועד לעולם מלכותו כבוד שם ברוך, and Moshe taught these words to us, so we can also use them to praise Hakadosh Baruch Hu. Throughout the year, we say these words silently because these words were taken from the malachim. The Midrash explains, "It can be likened to someone who stole jewelry from the king's palace and gave it to his wife. He tells her, 'Don't wear jewelry in a public place, only at home.' But on Yom Kippur, when we resemble the malachim, we can boldly proclaim this praise aloud, and therefore, we say out-loud כבוד שם ברוך ועד לעולם מלכותו ."
About Yom Kippur it states (Yoel 2:11), גדול כי מאוד ונורא 'ה יום , "For Hashem's day is great and very awesome." We don't eat and drink on Yom Kippur, and the Zohar explains that this is because Yom Kippur is a day that transcends this world. It is the day of Olam Haba.
The date of Yom Kippur (the tenth of Tishrei) is written in the Torah after several pesukim discussing the halachos of Yom Kippur (see Vayikra 16:29). Generally, the Torah first writes the date, and then it states the korbanos. But regarding Yom Kippur, it appears that the Torah almost doesn't want to mention the date. The Bnei Yissaschar (Tishrei 8) writes, "I think this is to reveal to us the holiness of the day...that we should know that Yom Kippur is a concealed, divine day... It is Olam HaBa."
The Bnei Yissaschar adds that this is why many ehrlicher Yidden don't call the day “Yom Kippur.” Instead, they call Yom Kippur "The holy day-Yom kadosh.” This is because the day comes from a very high place, and we want to conceal it. Bnei Yissaschar writes, "Also, the masechta dedicated to the laws of Yom Kippur isn't called 'Yom Kippur' [unlike masechtos Shabbos, Rosh Hashanah, Succah, and Pesachim, that are named after the yom tov]. The masechta for Yom Kippur is called 'Yoma,' which means 'Day' [and it doesn't tell us which day]. Once again, this is because of the exaltedness of the day that we conceal it.
There is another wonderful source that Yom Kippur isn't part of the time in this world. It states (Vayikra 16:2) אל עת בכל יבא ואל הקודש , "The [kohen gadol] should not come at all times into the Kodesh HaKodashim." He may only go there on Yom Kippur. The Kli Yakar explains the pasuk, עת בכל יבא ואל, he shouldn't enter the Kodesh HaKodashim on any date that is part of עת, time. He can only go to the Kodesh HaKodashim on a day above time, which is on Yom Kippur.
The Gemara (Shabbos 129) teaches, "A person should sell the walls of his home to buy shoes." The mekubalim explain that the earth was cursed (due to Adam HaRishon's sin, see Bereishis 3:17); therefore, one should wear shoes to separate himself from the impurity of the earth. However, we don’t wear shoes on Yom Kippur, and we don't wear shoes in the Beis HaMikdash. Mishnas Chassidim explains that it is beneficial for us to go barefoot on Yom Kippur and in the Beis HaMikdash because this enables us to acquire the holiness that's there.
The gabbai of the Sar Shalom of Belz zt'l saw his Rebbe inhaling deeply on Yom Kippur. "Are you ok?" the gabbai asked. "Perhaps you need to eat?" The Sar Shalom replied, "I'm fine. I just wanted to inhale the holy air of Yom Kippur."
Kol Nidrei
The Or HaChaim Hakadosh wrote in a letter, "A wealthy person bought me the honor to take out the sefer Torah for Kol Nidrei. When I opened the aron kodesh, a bright light filled the beis knesses. It was like the gates of Gan Eden opened up."
Klal Yisrael says Kol Nidrei with awe and passion, but many wonder what is so special about Kol Nidrei that it touches people's hearts. Kol Nidrei is essentially hataras nedarim, annulling vows. We make hataras nedarim on erev Rosh Hashanah, too; it isn't recited with the awe of Kol Nidrei. What is its significance?
- Zohar teaches that by saying Kol Nidrei, we annul Hashem's oaths. It is possible that Hashem decreed a harsh decree due to our sins, and He established it with an oath, a שבועה. Even if we do teshuvah and succeed in rousing Hashem's compassion, what do we do with the oath? Hashem's oath is annulled with the Kol Nidrei. We aren't only annulling our vows but also Hashem's vows so that He can give us a good year.
- Reb Pinchas of Koritz zt'l (Imrei Pinchas, Yom Kippur ז"תקל) says, "Before Kol Nidrei, malachim and neshamos come down from their place in heaven. Nothing can host malachim and neshamos more than tears that we shed before Hashem." Therefore, we begin Yom Kippur with thoughts of teshuvah, which enable us to daven together with the malachim and holy neshamos.
- The Baal Shem Tov zy'a explains that Klal Yisrael knows (they feel it in their subconscious souls) that when they recite Kol Nidrei, the Satan is trying with all his might to prosecute against them. This is the reason Yidden are inspired to do teshuvah at this time.
The Gemara (Yoma 20.) says, "השטן is gematriya 364, because the Satan has permission to prosecute 364 days a year. On...