Toward the end of his life, the renowned Jewish legal authority, the Chatam Sofer, became seriously ill, suffering from terrible pains in the area of his Brit Milah [sexual organ]. In a letter, he disclosed his apprehension that the suffering had come upon him because of some sin.

Reviewing his life, he did a scrupulous self-accounting, hoping to discover the cause. But he could not recall ever having committed a sexual transgression.

Finally, he writes, he understood the reason for his suffering. He was being punished for not having taught enough about shmirat habrit, the obligation to guard the laws of sexual purity; for it was his custom to speak to his congregation about the importance of this matter just one time a year, on the eve of Yom Kippur.

The Chatam Sofer chose that day because Yom Kippur is the paramount day of the year for Tikun HaBrit, the rectification of sexual transgressions. In fact, according to the esoteric understandings of Torah, all of the day's prayers and practices are directed toward rectifying this part of our lives.

The saintly Rebbe of Gur, Rabbi Yehuda Ari Leib, the Sfat Emet, writes that while all of humanity comes before G-d for judgment on Rosh HaShanah, the holiday of Yom Kippur is exclusive to the Nation of Israel in its aspect of Tikun HaBrit (Sfat Emet, Yom Kippur, 5656). This is because the Covenant of the Brit (sexual purity) between G-d and Avraham is unique to the Jewish People, as it says, "And G-d said to Avraham, therefore thou shall safeguard My brit, thou and thy seed after thee in their generations." (Bereshit 17:9)

The Sfat Emet states: "And regarding this matter, it is written in Pirchei D'Rebbi Eliezer that Avraham Avinu circumcised himself on the day of Yom Kippur." He notes that the phrase "in the selfsame day" is mentioned in the Torah both in reference to Avraham's circumcision (Bereshit 17:26) and to Yom Kippur (Vayikra 23:28).

Also, he notes, the final Hebrew letter in each word of the phrase, "your sins before the L-rd" (Vayikra 16:30), referring to the confession and atonement of Yom Kippur, spell milah, from the term for circumcision, Brit Milah. This teaches that the removal of the orlah (foreskin), and the removal of the spiritual orlah caused by sexual transgression, is intrinsically connected to Yom Kippur.

The Sfat Emet notes that on Yom Kippur eve, we enwrap ourselves in a tallit (prayer shawl) because the tzitzit (fringes) hint at the importance of guarding the eyes in order to safeguard sexual purity. To substantiate this, he cites the Talmud's recounting of an errant student who was saved from the lures of an irresistible prostitute through the merit of his tzitzit (Menachot 44a).

"Furthermore," he writes, "Just as there is one special day in the year, Yom Kippur, to purify all of the days that have passed, so too there is one sinew of the body, the sinew of the milah, whose purification purifies all of the rest."

In many congregations, just prior to the Kol Nidre service, the penitential prayer, Tefillah Zaka is recited to help prepare our hearts for the long day of confession ahead. The prominent theme of the prayer concerns transgressions against the brit. The commandment concerning the brit includes not only the act of circumcision, but also the requirement that a Jew conduct his sexual life in holiness. Therefore, we commence Yom Kippur by admitting our erring ways:
And now, my L-rd, I did not listen to Your voice, and I followed after the counsel of the evil inclination... and not only did I not sanctify my organs and limbs, but I made them impure.... Through my evil fantasies and foreign thoughts, I came to emit semen in vain, both by accident and knowingly, through impure seminal emissions that pollute the whole body.
The Sfat Emet explains that Tikun HaBrit lies at the essence of the majestic ceremony of Kol Nidre. Just as HaShem (G-d) is a purifying mikveh (ritual bath) for the Jewish People, so too is the Torah, which is completely made up of the Names of the Blessed One, Holy Be He.

"Therefore," the Sfat Emet writes, "we take out Torah scrolls at Kol Nidre and make a confession over sins and blemishes to the sign of the holy brit, for the written Torah and the Covenant of the brit are one and the same."

A thorough understanding of this concept ? how the Torah and the brit are one - is beyond the scope of this essay. Nonetheless, the key to the secret is the recognition that both the written Torah and the brit are identified with the sefirah of Yesod, the spiritual channel that brings Divine Illumination into the world.

Thus, sexual sins that damage the Yesod can be rectified through an active connection to Torah, which strengthens the Yesod.

The Kabbalistic explanations of the Hasidic master, Rabbi Nachman of Breslov, dealing with Jewish Law are recorded in Likutei Halachot, written by his foremost student, Rabbi Natan. Citing many of the same observations as the Sfat Emet, he elaborates on the inner connection between Yom Kippur and the rectification of sexual sins ("Laws of Yom Kippur", 1).

He also explains that the Tikun HaBrit of Yom Kippur is the encompassing tikun, what he calls the Tikun HaClalli because the sexual lust is the father of all of man's desires. Furthermore, because the organ of the brit is associated with the sefirah of Yesod, the foundation of all of the sefirot (Divine illuminations), in atoning for sexual transgressions, a person rectifies his entire spiritual blueprint.

Rabbi Nachman teaches that Yom Kippur became the Day of Atonement precisely because it was the day that Avraham Avinu circumcised himself, marking the first time that a man purged himself from the husk of the impure orlah (foreskin), which acts to separate a man from his Maker. This revolutionary act of Avraham Avinu is what endowed the day with the power to cleanse the sins of the Jewish People at Sinai.

Following the sin of the Golden Calf, Moshe ascended Mt. Sinai for 40 days to ask forgiveness from HaShem. Rabbi Nachman continues the same theme: "For the forgiveness that Moshe won for the Jews was actually over transgressions to the brit, for the sin of the Golden Calf was over sexual misconduct, as our sages have taught us - the Jewish People only worshiped idols to provide an excuse for publicly engaging in sexual licentiousness." (Sanhedrin 63A; Rashi on Shemot 32:6) "This rectification of the brit made this day the Day of Atonement for all generations."

Rabbi Nachman explains that all of the service of the Kohen HaGadol (High Priest) on Yom Kippur was a national Tikun HaBrit. Precisely because the Kohen HaGadol had to separate himself from forbidden relationships more than any other Jew, he was entrusted with the task of seeking atonement for the nation on Yom Kippur.

His exalted holiness came from safeguarding his sexual purity; the reason he was kept awake all night was in order to avoid a nocturnal emission, which would nullify him for service. "This is also the reason why the Kohen HaGadol was anointed with the special Oil of Anointing, which endowed him with supreme spiritual knowledge (daat) that only comes through the holiness of safeguarding one's sexual purity, embodied in Tikun HaBrit. For all of the Kohen HaGadol's service on Yom Kippur, and the atonement of the nation, was dependent upon this transcendent holiness and daat."

This demand for absolute sexual purity was also the inner reason that the Kohen HaGadol had to be married. "For a person who isn't married is considered to have sexual blemishes. This is the reason that the deaths of Aharon's sons are mentioned in the Yom Kippur Torah reading, for their sin in entering the Holy of Holies was in not being married, for only one who has achieved Tikun HaBrit in wholeness can bring down the exalted daat." (ibid.)

This is also the meaning of the verse that depicts the Yom Kippur service, "With this, Aharon shall enter the Holy of Holies" (Vayikra 16:3) - with this absolute sexual holiness of Tikun HaBrit. Use of the same term "this" (zot) regarding the brit strengthens the analogy: "This (zot) is the brit that you must guard." (Bereshit 17:10) In light of these understandings, it is clear why we read the Torah portion dealing with forbidden sexual relations on Yom Kippur, in its aspect of Tikun HaBrit.

"Therefore," Rabbi Nachman continues, "It was on Yom Kippur that Moshe brought the Torah to the Jewish People, because the foundation of receiving the Torah is Tikun HaBrit. And for this reason six people are called to read from the Torah on Yom Kippur, because the number six represents Tikun HaBrit (the sefirah of Yesod, the sixth of the lower sefirot-channels). And marital relations are also forbidden on Yom Kippur in order to merit receiving the Torah, just as Moshe was separated from all things, and in this manner, we merit atonement, through the holiness of the brit."

Studying the teachings of Rabbi Nachman, one realizes that everything on Yom Kippur has to do with Tikun HaBrit. For instance, "All of the sacrifices in the Temple on that day were for the rectification of sexual transgressions, in order to subdue the animal drives that bring about sexual sin, as the holy Zohar states: 'Don't be like a horse or a mule that have no understanding.'" (Zohar, Vayikra 49b)

What distinguishes man from a beast is his intellect (daat) and, as we have learned, the illumination of daat can only be attained through Tikun HaBrit. For this very same reason, we fast on Yom Kippur, in order to conquer our animal lusts. And, Rabbi Nachman explains, "This is why wearing leather shoes is forbidden, just as Moshe was told to remove his shoes before approaching the burning bush, to symbolize the need to detach himself from physicality and its lusts."

As might be expected, the final Yom Kippur prayer, Neilah, is also filled with significance. Just as Neilah seals the day and its forgiving decree, so too is the sign of the brit considered the seal of the King. Thus, the Neilah prayer comes to certify with its stamp of finality that the Tikun HaBrit is complete.

If all of these insights are true (and who are we to doubt the Torah wisdom of Rabbi Nachman, the Sfat Emet and the Chatam Sofer?), then why have the majority of us never been taught all of these exalted matters? Perhaps, the most diplomatic answer is to be found in the teaching of Kohelet that for everything there is a time (Kohelet 3:1). In our age of wanton sexual transgression, the time has certainly come.