October 6, 2025|י"ד תשרי ה' אלפים תשפ"ו The King Always Has One More Move: Yom Kippur, Faith and the Power of Teshuvah By Rabbi Jonathan Muskat

Germany, 1913. A young university student in his mid-twenties named Franz had grown up Jewish, but Judaism felt to him more like a barrier than a gift. It stood in the way of career advancement, a university appointment, and full acceptance among his peers. Many of Franz’s Jewish friends had already converted to Christianity. In his intellectual circles, Christianity was praised as more advanced than Judaism. Eventually, Franz resolved to follow their path.

But Franz was an intellectual. He didn’t want a superficial conversion. Since Jesus himself was Jewish, Franz reasoned that the most authentic way to become Christian was first to reconnect briefly with Judaism, and then convert from within. Though he hadn’t been inside a synagogue in years, he decided: the High Holidays are coming. I’ll attend Rosh Hashanah and Yom Kippur, and then I’ll convert.

He wrote home to his mother: “Mom, I’m coming home for Rosh Hashanah. Get me a ticket – I’m going to shul with you!” She was overjoyed. They went to the Reform synagogue in Kassel.

A few days later, she asked him why. Franz answered, “I’ve decided to convert. But I want to convert like Jesus, from within Judaism. So I’ll go to shul one last time on Yom Kippur, and then I’ll become a Christian.”

His mother interrupted: “What?! Don’t you dare come to synagogue to make a mockery of us! If you try, I’ll tell the ushers to throw you out!”

Franz was bewildered. The one time he truly wanted to reconnect – they wouldn’t let him. What was he to do?

And this brings us to our own Yom Kippur question. Today, we pour our hearts into prayer and tears. We reach the heights of Neilah, and when the shofar sounds, we are assured that itzumo shel yom mekaper – the very essence of the day has cleansed us.

And then, what happens? We go home, eat, rejoice. But first, we daven Maariv. And in that very first Shemoneh Esrei we say: Slach lanu Avinu ki chatanu – Forgive us, Father, for we have sinned.

Stop. Didn’t we just finish Yom Kippur? Didn’t we just wipe the slate clean? Why are we asking forgiveness again minutes later?

Some answer: we don’t alter the liturgy, so we keep saying slach lanu. Others say: perhaps we’re praying for Jews who didn’t merit a Yom Kippur, and we ask forgiveness on their behalf. The cynics say: by Neilah we were starving, distracted, unfocused, and maybe not fully forgiven. The humble say: a true servant of God is never certain – always striving higher.

All true. But consider a different story.

In the Louvre once hung a painting by Friedrich Moritz August Retzsch called Checkmate. It showed two chess players: one was Satan, confident and arrogant, the other a forlorn man who seemed doomed. If Satan won, he would win the man’s soul. Legend has it that a chess grandmaster once studied the painting and shouted: “It’s not checkmate! The King has one more move!” In other words, even when it seemed the man was lost, there was still hope.

The message is clear: no matter how hopeless life feels, no matter how far we’ve strayed – the King, Hashem, always gives us one more move. Always one more chance for teshuvah.

This is the teaching of the Chiddushei HaRim, the first Gerer Rebbe:

ונראה כי העיקר הוא שבנ"י צריכים להאמין שיוה"כ מכפר. ואם ח"ו יש לו ספק ספיקא אם סלחו לו הרי חטא בידו. ועל זה מתפללים במוצאי יו"כ אולי לא היה לנו אמונה שלימה שיום כפור מכפר.

The essence of Yom Kippur, he writes, is not only that it atones – but that we must believe it atones. If we doubt it, that doubt itself becomes a sin. So right after Yom Kippur, we ask forgiveness again – not for the sins we confessed, but for not fully believing in Yom Kippur’s power.

And that is the challenge of modern man. Can we, rational, educated people, truly believe in the miracle of teshuvah? That an entire year of mistakes can be washed away in one day? It defies logic.

But the Torah insists: it’s real. The Yerushalmi in Makkot asks:

שאלו לחכמה חוטא מהו עונשו אמרו להם חטאים תרדף רעה
שאלו לנבואה חוטא מהו עונשו אמרה להן הנפש החוטאת היא תמות
שאלו לקודשא בריך הוא חוטא מהו עונשו אמר להן יעשו תשובה ויתכפר לו

Wisdom says: evil will pursue him. Prophecy says: the soul that sins shall die. Logic says: there’s no hope. Justice says: no forgiveness. But God says: Ya’asu teshuvah v’yitkaper lo. Let them repent – and they will be forgiven.

Against all reason, there is mercy. Because the King always gives one more move.

And now back to Franz. Turned away from his mother’s synagogue, he went instead to a more traditional shul in Berlin. He went on Kol Nidrei. He returned on Yom Kippur day. And what he experienced changed him forever.

Not long after, he wrote to a friend: “After prolonged, and I believe thorough, self-examination, I have reversed my decision. I will remain a Jew.”

That Franz was Franz Rosenzweig – one of the most influential Jewish thinkers of the 20th century. He became more observant, never fully Orthodox, but forever transformed. He never described exactly what he felt that Yom Kippur—but he knew. He had touched the irrational, mystical power of the day.

Perhaps Rosenzweig experienced what the Gemara describes:

נתעטף הקדוש ברוך הוא כשליח ציבור והראה למשה סדר תפילה… כל זמן שישראל חוטאין, יעשו לפני כסדר הזה, ואני מוחל להם.

God wrapped Himself in a tallit like a shaliach tzibbur, revealed to Moshe the order of prayer, and said: “Whenever Israel sins, let them do this, and I will forgive them.”

What does it mean that God wrapped Himself in a tallit? That we cannot see His essence, but we can feel His presence. We cannot touch Him, but on Yom Kippur, we sense He is right here. As Rav Amital zt”l explained, God also taught us: just as He wrapped Himself, so must we. To be enwrapped in a tallit means to embody mercy, compassion, and humility – to give, to love, to help, quietly and without fanfare.

This leads us naturally to Yizkor. As we prepare to recite it, we remember our deceased mothers, fathers, grandparents, and relatives. We pray for them, give charity on their behalf, and support the shul – the anchor of our community, so vital and needed. Their memory and merit wrap around us, just as God wrapped Himself in the tallit, teaching us closeness, mercy, and compassion.

Even though they are no longer physically present, their influence endures. Through our prayers, our giving, and our acts of kindness, we continue their work. We uphold the spiritual roof over our homes and our community, creating a shelter of love, mercy, and holiness. Yizkor reminds us that we are part of a chain, a living continuity, connecting past, present, and future.

So as we leave this holy day, let us carry the lessons of Franz Rosenzweig, the painting Checkmate, and the tallit together. Let us live with awareness, with mercy, and with courage. Let us embrace the gifts and the responsibilities of another chance, another move, given to us by the King.

As we step back into the world, let us carry Yizkor in our hearts: the memory of those who came before us, the lessons they taught, and the values they embodied. Let our prayers, our giving, and our deeds create a world where mercy, compassion, and love are alive and enduring. Let the King’s one more move inspire us to continue building homes, families, and communities fortified by kindness, holiness, and unwavering faith.

May we leave Yom Kippur transformed, strengthened, and inspired, always aware that no matter how dark the board may look, the King always has one more move.