I shared the following three stories on Erev Rosh HaShanah:

From the Depths of the Heart (Nachlei Binah p. 317 #632 Tehillim Ben Beiti, Rabbi Eliezer of Komarno)

One time a Jewish peasant boy came to the big town to celebrate Yom Kippur. He didn’t know how to pray. He could not even read the letter Alef. He only saw that everyone was traveling to the synagogue to participate in the holy prayers. He thought, “If everybody is going to town, I must go too!”

He arrived at the town synagogue with his father and watched the congregants crying and singing together, swaying to and fro. He turned to his father and asked, “Father, what is this all about?” His father turned to him and said, “The Holy One blessed be He sits enthroned in the heavens and we pray all year long to Him. We especially pray during these two days of Rosh Hashanah and Yom Kippur when the whole world is being judged and each person is being judged for the rest of the year.”

The son responded, “Father, what am I to do since I do not know how to pray?”
His father quickly said to him condescendingly, “All you have to do is be quiet and listen to the other Jews praying. That is enough for you.”

“But Father, if I don’t know what these people are saying how is that going to affect God’s decision? How is being silent going to help me?” His father became unnerved and blurted out, “Listen, you should be quiet so no one will know you’re an ignorant peasant!” The son stood still for a couple of minutes as his father and the rest of the congregation continued praying, and then the young boy stood up and in a loud voice stated: “I am going to pray to God in the way I know best. I will whistle to God as I whistle to my flock of sheep.”

He began whistling the sweet calls most shepherds know. His father was enraged. The boy continued whistling with all his might, not caring what other people thought.

Now it happened that this particular Yom Kippur all the heavenly gates were shut. Suddenly, because of this peasant boy’s pure whistling from his heart, all the gates burst open. The prayers of Israel were finally heard.

A Tzaddik’s Repentance

More than 1000 years ago, there lived a great and holy leader and teacher called Rabbi Saadiah Gaon (882–942). The Gaon (as the leading sages of Babylonian Jewry were titled at the time) had many hundreds of pupils, and all of them had a great thirst to learn. Even a casual movement or word from their revered teacher provided them a lesson for life.

One winter morning, two of his pupils happened to be walking in the mountains when they heard a strange sound on the other side of a hill. When they approached the summit they saw, to their great surprise, their master sitting on the snow-covered ground, weeping, praying and engaging in other acts of penitence. What could a tzaddik (perfectly righteous person) such as their teacher possibly need to repent for? Could he have committed some sin, G‑d forbid? They hurriedly departed from that place. But later that day, they could no longer restrain themselves and asked their teacher what the scene they had witnessed had been about.

“I do that every day,” he said to them. “Every day I repent and plead with G‑d to forgive my shortcomings and failings in my service of Him.”

“Your failings?” they asked. “Of what failings does the Gaon speak?”

“Let me tell you a story,” said Rabbi Saadiah. “Something that happened to me a while ago.”

“At one point in my life, I decided that all the honor and attention I was receiving from everyone around me was interfering with my service of the Creator. G‑d must be served with joy, and without complete humility, joy is impossible. So I decided that I would spend several months in a place where no one recognized me.

“I dressed in simple garments and began my self-imposed exile, wandering from town to town. One night I was in a small inn run by an old Jew. He was a very kind and simple man, and we spoke for a while before I went to sleep. Early the next morning, after I had prayed shacharit (the morning prayer), I bade him farewell and was again on my way.

“What I didn’t know was that several of my pupils had been searching for me, and several hours after I left the inn they appeared, hot on my trail. ‘Did you see Rabbi Saadiah Gaon?’ they asked him. ‘We have reason to believe that he was here.’

“‘Saadiah Gaon?’ replied the bewildered old Jew. ‘What would the great Rav Saadiah be doing in a place like mine? Rav Saadiah Gaon in my inn? No . . . I’m sure that you are very mistaken! There was no Rav Saadiah Gaon here!’

“But when the young men described me to him and explained about my exile and ‘disguise,’ the old Jew grabbed his head and cried: ‘Oy! Rav Saadiah! Rav Saadiah was here! You are right! Oy, Oy!’ and he ran outside, jumped into his wagon and began urging his horse to go as fast as possible in the direction I had taken.

“After a short time he caught up to me, jumped from his carriage and fell at my feet, weeping: ‘Please forgive me, Rav Saadiah. Please forgive me. I didn’t know that it was you!’

“I made him stand up and brush himself off, and then said to him: ‘But my dear friend, you treated me very well, you were very kind and hospitable. Why are you so sorry? You have nothing to apologize for.’

“‘No, no, Rabbi,’ he replied. ‘If I would have known who you are, I would have served you completely differently!’

“Suddenly I realized that this man was teaching me a very important lesson in the service of G‑d and in the way I treat others, and that the purpose of my exile had been fulfilled. I thanked and blessed him, and returned home.

“Since then, every evening when I say the prayer before sleeping, I go over in my mind how I served G‑d and my fellow man that day. Then I think of that old innkeeper, and say to myself: ‘Oy! If I had known about G‑d in the beginning of the day what I know now and if I had only remembered that that person I spoke to today was created in the image of G-d, I would have served Him completely differently!’

“And that is what I was repenting for this morning.”

A Pound of Candles

In his youth, the famed Maggid of Zlotchov, Rabbi Yechiel Michel, lived in a certain town, where he would sit all day in the local Beit Midrash (study hall and synagogue) and pursue his studies.

In that town there lived a simple Jew who earned his livelihood by transporting travelers and merchandise in his wagon. One day, the wagon driver came to the local rabbi in a state of great distress. “Help me, Rebbe!” he wept. “I have committed a terrible sin. I have desecrated the holy Shabbat. How can I atone for my transgression?”

“How did this come to pass?” asked the Rabbi.

“Last Friday,” the man explained, “I was returning from the marketplace with a wagonload of merchandise when I lost my way in the forest. By the time I found my way to the outskirts of the city, the sun had already set. So preoccupied was I with my worry over the merchandise, that I failed to realize that the Shabbat had arrived until it was too late…”

Seeing how broken-hearted the man was, the rabbi comforted him and said: “My son, the gates of repentance are never closed. Donate a pound of candles to the synagogue and your transgression will be forgiven.”

The young prodigy, Rabbi Michel, overheard this exchange, and was displeased by the rabbi’s approach. “A pound of candles to atone for violating the Shabbat?” he thought to himself. “The Shabbat is one of the most important mitzvot of the Torah. Why is the rabbi treating the matter so lightly?”

That Friday afternoon, the wagon driver brought the candles to the synagogue. As Rabbi Michel watched disapprovingly from his table against the back wall, he placed them on the lectern for the synagogue beadle to light in honor of the Shabbat. But this was not to be. Before the beadle arrived, a stray dog carried off the candles and ate them.

The distraught penitent ran to report the incident to the rabbi. “Woe is me!” he wept. “My repentance has been rejected in Heaven! What shall I do?!”

“You’re making too much of the matter,” the rabbi reassured him. “These things happen — there’s no reason to deduce that G-d is rejecting your repentance. Bring another pound of candles to the synagogue next week, and everything will be alright.”.

But when the beadle lit the candles on the following Friday afternoon, they inexplicably melted down, so that by the time Shabbat commenced, nothing was left of them. And upon his third attempt on the week after that, a strong wind suddenly blow out the candles just when Shabbat began and it was not possible to relight them.

The rabbi, too, realized, that something was amiss, and advised the wagon driver to seek the counsel of the great Chassidic master, Rabbi Israel Baal Shem Tov.

“Hmm…” said the Baal Shem Tov, upon hearing the man’s story. “It seems that a certain young scholar in your town finds fault with the path to repentance that the rabbi has prescribed for you. Never mind. Next week, donate another pound of candles to the synagogue. This time, I promise you that everything will be alright. And tell Rabbi Michel that I would be honored if he could trouble himself to come visit me.”

Rabbi Michel wasted no time in abiding by the Baal Shem Tov’s request. But no sooner had he and his coachman set out that all sorts of troubles beset their journey. First, the wagon tumbled into a ditch. Then, an axle broke many miles from the nearest town. After which they lost their way altogether. When they finally found the road to Mezhibuzh it was late Friday afternoon and the sun was about to set. They were forced to abandon the wagon and continue on foot – fearing the entire way that the sun would set and they would, at any moment, violate the Sabbath.

Rabbi Michel arrived at the Baal Shem Tov’s door an hour into Shabbat, weary and traumatized by his near-violation of the holy day. “Good Shabbat, Reb Michel,” Rabbi Israel greeted him, “come in and warm yourself by the fire. You, Reb Michel, have never tasted sin, so you did not comprehend the remorse a Jew feels at having transgressed the will of his Father in Heaven. Given the mishaps on the way here, I trust that you now understand something of the agony that our friend experienced. Believe me, his remorse alone more than atoned for his unwitting transgression…”

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