This Shabbat is characterized by teshuvah, repentance. Of all the Mitzvot in the Torah, Teshuvah is the most potent. Each Mitzvah forges a bond between a finite human being and an infinite G-d. No small feat. But teshuvah reconnects us after that bond has been severed through sin.

No other Mitzvah can act as an antidote to sin. No other Mitzvah can rebuild a fence that was trampled in our haste to pursue our fancy. Only Teshuvah can do that.

The difference between teshuvah and other Mitzvot is like the difference between food and medicine. Healthy people eat healthy food to ensure they remain healthy. Ill people must take medicine to recover their health. In terms of volume, one must eat much more food than medicine to maintain one’s health. It takes only one pill a day to restore one’s health, but three square meals to maintain it.

This is only surprising to those who don’t know what is packed into a single small pill. If we understood the potency of the pill, we would never wonder about that.

The same applies to teshuvah. A regular diet of Mitzvot is like eating healthy meals. Teshuvah is like a pill for when we have fallen ill. It is a single Mitzvah, but it is so potent that it can uproot sin, restore spiritual health, and enable us to recover. (Likutei Torah, Devarim, p. 45b.)

The question is how. How does this pill work? When illness takes hold of our body, medications either boost our immune system or fight off the invading cells. But how does the teshuvah pill work?

The answer is that it redefines the underlying meaning of the sin for which we repent. But to understand this, we must examine another fascinating aspect of teshuvah.

The Backward Mitzvah
Many Mitzvot require preparation. Think of Passover: you can’t enjoy the Seder table without investing days and weeks in preparation. You can’t enjoy your Sukkah without building it first. You can’t perform circumcision without preparing for it and acquiring the necessary tools.

Teshuvah also requires preparation, but it is the oddest type of preparation. You can’t fulfill the Mitzvah of teshuvah without having sinned first. If that is not weird, I don’t know what is.

Imagine your boss tells you that he wants you to take a workshop on transparency, but to prepare for the workshop, you need to embezzle first.

That would be weird unless you were hired to embezzle. Some people are hired by companies to expose their vulnerabilities. They hack encrypted security systems to identify weaknesses and then build patches to shore up the gaps. Their job is to probe for weaknesses before a real fraudster does.

These ethical hackers do the same things criminal hackers do, but they are not actually committing a crime. They are strengthening the company’s security. Imagine you were one of these ethical hackers and were caught red-handed by the FBI. As far as they know, they had reeled in a big fish. But then you pull a card out of your back pocket and, voila, the crime is revealed to be a sanctioned operation. You go from zero to hero overnight.

The same applies to teshuvah. When you sin, you don’t just look like a sinner; you really are one. Just like every other sinner. But G-d put a card in your back pocket, and you can pull it out after every sin. It doesn’t matter how many times you break the law; the card works every time. That card is teshuvah.

When you repent, you reveal that the true you was never invested in the sin.

Your conscious thought chose to sin. But your deepest essence of Divine goodness, concealed behind layers of ego, betrayal, fear, jealousy, and selfishness, never wanted to sin. It objected the entire time, though you weren’t conscious of it. And when you sinned despite that objection, the real you saw it as an opportunity for teshuvah. What was at first a sin became a signpost on the road to repentance.

The teshuvah pill changes the sin’s dynamics in retrospect. That is why it must be so potent. It must reach back into an act from the past, uproot the intentions you consciously embedded in it, launder it, and wash those intentions away. Then it must invest that sin with a new intention: the intention to repent. When that happens, it is no longer merely a sin. It becomes a step toward teshuvah.

The Oath
This works so long as we remain connected with G-d. So long as we don’t break with the foundational covenant of Judaism that says, G-d is mine and I am His. Breaking from that is an entirely different story.

An analogy is offered from a king who rewarded his loyal servant with a grand estate. Years later, the servant fell out of favor, and the king tried to reclaim the estate. However, the servant successfully sued in court, forcing the king to admit that once he had gifted the property, he could not reclaim it.

One day, the king caught his former servant planning a treasonous plot. At this point, the courts backed the king. If the servant annulled the oath upon which the king’s commitment was based, the king was no longer bound by his oath.

The same is true for us. So long as we commit infractions out of habit, passion, anger, or greed, we don’t upend our oath. We were simply overtaken in a moment of weakness, and we jump back on the wagon. We do this through teshuvah, revealing that the sins were ultimately a prelude to teshuvah.

However, if we break with G-d completely and declare ourselves no longer beholden to Him, we undo the basis for G-d’s oath to us. That is why the Talmud proclaims, “Even when we sin, we remain Jewish.” So long as we don’t betray our essential identity, our covenant with G-d will hold. (Torat Moshe (Chasam Sofer) Devarim 29:12.)

Two Stories
Rebbetzin Esther Jungreis, of blessed memory, was once on a plane, and she engaged her Jewish seatmate in conversation. When the non-kosher meal arrived, her seatmate accepted it. As he was unwrapping the tray, she said, “How can you eat this? You took an oath.” He looked at her incredulously. “What oath did I take?” “To eat Kosher,” she replied. “Lady,” he said, exasperated, “I never took such an oath.” “Yes, you did,” she replied. “It was at Sinai, and I was there to witness it.”

Tvi Yechezkeli, a famous Israeli journalist, grew up secular and became fully observant later in life. The event that triggered his transformation was an interview he once conducted with a terrorist. Yechezkeli asked him whether he would kill him if he had the chance. The terrorist confirmed that he would.

Yechezkeli asked why, considering he had done nothing to him. The terrorist explained that it was because Yechezkeli was a Jew.

Yechezkeli thought this strange since he didn’t feel very Jewish. He was just a member of the human race.

The terrorist’s reply changed his life. “Don’t be stupid. If I killed you, I would rejoice for the rest of my life for killing a Jew. So, if you would die as a Jew, you may as well live as a Jew.”

Right then and there, Yechezkeli decided to stop breaking the oath he had taken at Sinai. Once that was in place, the rest fell into place. His sins became signposts on his journey to teshuvah.