2025 Yom Kippur Evening: Checkers, Chess & New Choices

In 1863, two checkers champions — yes, you heard me right, checkers champions — James Wyllie and Robert Martins, played a 40-game match. Of those 40, 21 were the exact same game from start to finish. Twenty-one times, move for move, the game repeated. The other 19 began with the same opening moves, and all forty games ended in a draw.

Don’t tell my five-year-old this, but checkers … well … it just isn’t that interesting. By 1863, checkers had been “solved,” as every position could be played perfectly to guarantee at least a draw. Competitive checkers is a game of memorization and recall, not a game of skill.

Chess, however, is a different animal. In fact, the number of possible chess games on that simple 8-by-8 board is greater than the number of atoms in the universe.

A chess game is divided into three sections: opening, middlegame, and endgame.

The beginning of a chess game consists of memorized moves and patterns, with players moving their pieces around the board in rote recall rather than strategic thinking or creativity. Similarly, the end of the game is like this as well, as the dominant player closes in for checkmate by adhering to well-worn techniques. In chess, these memorized moves are called in book.

But in the middle … that’s where the beauty is.

The middle of a chess game is off book, where even the most experienced players can no longer rely on memorization or pattern recognition. They must think strategically and creatively and bring something new to each game.

A lot of our lives are in book. We wake up, follow the same routines, and replay familiar interactions:

“Good morning, good to see you.”

“Good morning!”

“How are you?”

“Fine. You?”

“Fine.”

“How’s the family?”

“Good. Yours?”

“Good. Thanks. Have a great day.”

Psychologists call these shortcuts heuristics. It’s a fancy word for the patterns and routines we use without realizing it.

These opening book heuristics make our lives easier, but they can also keep us locked in the same old patterns.

We replay the same arguments with the same people. We stumble into the same frustrations and repeat the same unhealthy habits. Our lives can run on autopilot, guided by heuristics that keep us from noticing new possibilities. Like those 21 identical checkers games, we move through the same sequences again and again. And the more often we drive down the same road, the easier it is to get stuck on that path.

But tonight, Kol Nidrei asks that we move from our repeated in book moves that we repeat and embrace the unknown newness of the middle game — to live off book.

Our lives have openings that are shaped by nurture and nature, and endgames often defined by the constraints of a life’s obligations and the fact of mortality. But tonight, we remember that we can move off book and create our lives anew. Kol Nidrei reminds us that some of our memorized routines should be changed. It’s time to see other people — and ourselves — with new eyes.

Ecclesiastes famously said: There is nothing new under the sun. And he was right. But he was only right if we do not heed the day’s challenge to change our ways, to make new vows and choices, to engage in t’shuvah with our loved ones, our friends … and ourselves. If we follow the same patterns and routines, then yes, there is nothing new under the sun.

But Yom Kippur insists that we do otherwise. We fast and rehearse our death, confronting the endgame of our mortality. But the purpose of Yom Kippur is not death — it is life. As our Machzor repeats: It is not the death of sinners that You seek, but that we turn from our ways … and live. The endgame of Yom Kippur is not resignation — it’s renewal. This is what it means to choose life.

Yom Kippur reminds us that we should do things differently. But more importantly, it comforts us with the knowledge that we can do things differently.

And practically speaking, what are some things you and I can do differently?

• In the middle of yet another argument, we can ask an honest, genuine question we otherwise wouldn’t.

• Before our hand reaches for the phone, or before the “opening moves” routine of getting out of bed, showered, and dressed, we can stop and take just 30 seconds for reflection and gratitude.

• When we come to CCI for a Shabbat service or program, sit in a different seat. Learn the name of just one new congregant or guest, and have a conversation.

The Harvard psychologist Daniel Gilbert has this idea that at some point in our lives, all of us think about what he calls The Sentence. Each of us has a different conclusion to the sentence, which is this: The human being is the only animal that …

Some people finish it with: The human being is the only animal that writes poetry … the only animal that makes jokes, has religion, thinks about where they came from, the only animal that plays chess …

This is Gilbert’s sentence: The human being is the only animal to think about and plan for the future.

The Jewish answer goes one step further: The human being is the only animal that does t’shuvah.

We can break with unhelpful and unhealthy in book patterns and create new ones.

We ask God to renew our days, but that can only happen when we renew ourselves.

Maimonides captures this powerfully when he writes,

Even though the sounding of the shofar … is a decree, there is a hint within it: Awake, sleepers, from your sleep, and slumberers, arise from your slumber. Search your deeds, return in repentance, and remember your Creator.

Maimonides refers to God as a Creator — not God the Lord, not Ruler of the Universe, not Avinu Malkeinu — but Creator. By relating to God as Creator, we remember that as God’s partners, we have not only the ability to create but the sacred responsibility to create.

The creation of our lives can be bold and daring, not reliant on old tropes or memorized patterns. Prove Ecclesiastes wrong: There can be something new under the sun. This year, YOU are the something new under the sun.

The movie Awakenings tells the true story of patients who were catatonic for decades. They were treated with an experimental drug that allowed them to temporarily awaken. One patient, Leonard, played beautifully by Robert De Niro, regains speech and movement, and in his excitement, he tries to communicate his new awareness and appreciation:

People have forgotten what life is all about. They’ve forgotten what it is to be alive. They need to be reminded. They need to be reminded of what they have and what they can lose. What I feel is the joy of life, the gift of life, the freedom of life, the wonderment of life!

By confronting our mortality on this sacred day, we too are jolted awake, and we are reminded of what we have and what we can lose. We hold a precious, holy, sacred gift. Let the piercing sound of the shofar wake us up to this realization. Let the words of Kol Nidrei inspire us to make new vows and new choices. And may our fast motivate us to create our lives anew, that we may choose life.