Yom Kippur 5786/2025
Prayers that are Too Hard to Say
Rabbi Robert Tobin
Bnai Shalom, West Orange NJ
L’shanah tovah. This morning, I need to ask for your patience, understanding and support as I struggle with this most sacred day of the year, in the wake of the loss of our beloved son, Yossi, yosef lev ben harav reuven tuvin v’talia, zikhrono livrakhah. I have been dreading this part of the yom kippur service, the coming of yizkor, since the first moments I was able to lift my head from the overwhelming grief of our loss in those first hours, days and weeks. This is the first yizkor since the day he died - the second day of shavuot - itself a yizkor day. To say that yizkor will be hard is a ridiculous understatement.
So when I’m done with what I want to talk about today, I have asked Rabbi Gerry Skolnik to lead us all in yizkor while I stand and pray with my family.
What I struggle with is the words of prayer book and especially of the machzor for Rosh Hashanah and today. In those first terrible minutes, I stood by Yossi, alav hashalom, and said the vidui. This is our rite of final prayers of forgiveness, ideally said by one whose death is imminent, but often said by others on their behalf. It is a Yom Kippur prayer, which I often help members of this community say for their loved ones. But it is now forever changed, maybe embittered, by our own experience. It asks for forgiveness for him, from him, and for mercy and love in his death, that he may be taken by God to the eternal life of the soul. It ends with those enabashed proclamations of faith in God and God’s power - the Shema, and Adonai Hu HaElohim, Adonai Hu HaElohim, Adonai Hu HaElohim. God is One. God is sovereign. God is God.
(Pause, gut check).
During the days of shiva and the thirty days of our shloshim, we were unbelievably supported by this community, our friends and family. You came, you called, you wrote, and you gave of your hearts, your experience and your generosity to care for us. You made sure we had everything we needed in the home, and a minyan for our kaddish every morning and every evening without fail for the entire month. I am sure we don’t know half of what was done for us, and we will be forever grateful.
As we gathered to pray, morning and night, the words of the siddur were jarring and painful. The dissonance between the perfect faith of those pages and what had just happened was undeniable. The gulf between what should be and what is, was impossible to bridge. What do we do when the prayers are too hard to say? When our lived experience wants to take our loss and throw it back in the face of God and say how dare you? When our mind reals from the enormity of it all and wants to reject all purpose, all meaning, and the very idea of God. A healthy, happy, hardworking, funny, loving, attentive, and beautiful young man does not just die in his sleep, and yet our son did.
At the funeral, I said I am grateful for Yossi’s life and everything that he was. And everything that he could have been, should of been in our life and his is now gone. And that truth isn’t in the siddur. Even harder though, are the words that are.
"Modeh Ani, I give thanks to You... who in mercy has returned my soul to me; great is Your faithfulness." But He doesn’t always, does He?
"Impress [these words] upon your children." (From the Shema, second paragraph - V'haya) How can I do that for him now?
"Recite them when you stay at home and when you are away, when you lie down and when you get up." But he didn’t rise up. And the very hardest...
l’ma’an yirbu y’meikhem vimei v’neikhem al ha’adamah ashe nishba’ Adonai l’avoteihem... So that your days and your children's days will be lengthened on the good land that the Lord swore to give to your ancestors.
Long days, many years. Promise after promise, ringing empty and hollow in the pain and anguish that has overcome us. Of course we are not the only ones. But in those moments, nothing matters. Meaning is elusive. Faith feels like an affront.
The greatest heretic of the Rabbinic tradition was Elisha ben Abuya. In Talmud Kiddushin 39b, He witnessed a child obeying his father’s request to climb a tree to shoo away the mother bird and gather the young from the next. The child fell and died. And the Torah says two things about that.
שַׁלֵּ֤חַ תְּשַׁלַּח֙ אֶת־הָאֵ֔ם וְאֶת־הַבָּנִ֖ים תִּֽקַּֽח־לָ֑ךְ לְמַ֙עַן֙ יִ֣יטַב לָ֔ךְ וְהַאֲרַכְתָּ֖ יָמִֽים׃ {ס}
Let the mother go, and take only the young, in order that you may fare well and have a long life.
כַּבֵּ֤ד אֶת־אָבִ֙יךָ֙ וְאֶת־אִמֶּ֔ךָ כַּאֲשֶׁ֥ר צִוְּךָ֖ יְהֹוָ֣ה אֱלֹהֶ֑יךָ לְמַ֣עַן ׀ יַאֲרִיכֻ֣ן יָמֶ֗יךָ וּלְמַ֙עַן֙ יִ֣יטַב לָ֔ךְ עַ֚ל הָֽאֲדָמָ֔ה אֲשֶׁר־יְהֹוָ֥ה אֱלֹהֶ֖יךָ נֹתֵ֥ן לָֽךְ׃ {ס}
Honor your father and your mother, as your God יהוה has commanded you, that you may long endure, and that you may fare well, in the land that your God יהוה is assigning to you.
The child was simultaneously observing the two mitzvot that promise long life as a reward, and died in the act.
Upon seeing this apparent contradiction, Elisha ben Abuya concluded that "leit din, v'leit dayan," meaning "there is no justice and no Judge". The irreconcilable lack of the promised reward in this world became a major trigger for his apostasy.
Everything we add to machzor for this day is about life and death, especially in this world.
As if faith itself is not enough, as if that is not hard enough, we get hit with the unetaneh tokef prayer, who will live and who will die, and how... and we are promised that teshuvah, tefillah and tzedakah - ma’avirin et ro’a ha gezeirah that repentance, prayer and generosity avert the badness or evil of the decree from God. We are faced with the Avinu Malkeynu, God please write us into the books of health, prosperity... life. And we face these words bereft of our son. How do we face prayers that are impossibly hard to say? What teshuvah are we supposed to do to make this better? What tefillah mitigates our loss? What tzedakah might ever make it okay?
For many, this is the hardest day of the year. There are many reasons why. First, the long hours. Second, fasting. And third, the intense Hebrew text creates an enormous barrier for the majority of the people in the room today.
No, these prayers are hard on every level. It is not easy. But who ever said life would be easy? Life can be unbearably hard. Love and loss can be felt like a physical pain that refuses to abate. And our tradition hands us this book and says to us, gather a room of people who care and say these prayers. Say them today. Say them tonight. Say them tomorrow. Say them for as long as breath is in you.
I will, but I will not say just those words. When Job had lost nearly everything and everyone he ever loved, and the world gaped at him in horror and judgement, he said,
חַי־אֵ֭ל הֵסִ֣יר מִשְׁפָּטִ֑י וְ֝שַׁדַּ֗י הֵמַ֥ר נַפְשִֽׁי׃
By God who has deprived me of justice!
By Shaddai who has embittered my life!
כִּי־כׇל־ע֣וֹד נִשְׁמָתִ֣י בִ֑י וְר֖וּחַ אֱל֣וֹהַּ בְּאַפִּֽי׃
As long as there is life in me,
And God’s breath is in my nostrils,
חָלִ֣ילָה לִּי֮ אִם־אַצְדִּ֢יק אֶ֫תְכֶ֥ם עַד־אֶגְוָ֑ע לֹֽא־אָסִ֖יר תֻּמָּתִ֣י מִמֶּֽנִּי׃
Far be it from me to say you (my pious accusers) are right;
Until I die I will maintain my integrity.
These words, also from our sacred writings, ring true. There is a wrongness to our loss that must be proven right if anything else we say and pray should ever be held to be true. The wrongness is real. The wrongness is truth. And it too has to find a place in prayer.
“How are you doing, Rabbi? How is your family?” Most of the time, my answer has been “terrible, as you might expect.” Maybe as well as you could hope, given what has happened. We have experienced, are experiencing, genuine trauma.
Trauma is not just sadness; it is the shattering of the assumption that the world is safe and ordered. Losing a loved one—a parent, a partner, a friend, and especially a child—is the ultimate proof that the most basic prayer, the prayer for life itself, was either unanswered or the answer was terrifying.
Which, of course, brings us to the Unetaneh Tokef. After months of struggling with the daily prayers, the High Holy Days arrive, bringing with them a compressed dose of confrontation that is somewhere between a sledge hammer and a slap.
On Rosh Hashanah it is written and on Yom Kippur it is sealed, "Who shall live and who shall die,” and even how they will die. These words acknowledge the vulnerability of life, but for the mourner, the vulnerability has already passed into permanent reality. We already know the answer. We stand here now as the proof of the prayer's terrible inevitability and we look back at last year and gape.
Is this what was written? Was this God’s choice? Are we praying that teshuvah tefillah and tzedakah will stay the hand of the Angel of Death? We can pray, but that is too much for anyone to hope for. We are going to die, and prayer itself does not stop that. Some believe it is a prayer for the manner of death, who by fire, who by water, who in old age and who not... but the combinations are a torture to even think about. Is a peaceful death at young age more acceptable than a painful death at old age?
The prayer, of course, was not meant to look back but to look forward. It is to make us think about life lived by the living, with teshuvah, tefillah and tzedakah as our tool kit to face hardships and challenges awaiting us in the year ahead. So we must read the unetaneh tokef prayer sequentially. On Rosh Hashanah it is written and on Yom Kippur it is sealed, and whatever that is, however that comes into your life, teshuvah tefillah and tzedakah are to be yours to use and apply to the terrible and the unthinkable, and they will make the horrible less horrible. They are ma’avirin et ro’a hag’zeirah. They mitigate the bad decree in some real way.
That, I believe to be true. It is honest. It is not denial of what has happened, or a childish hope to be spared the terrible things in life. It is a choice. A commitment. The kind of thing we say when we are in a loving relationship and we promise how we are going to behave, not that we are going to be perfect.
Look around this room. Every person who stays for Yizkor is a fellow traveler, carrying a piece of loss. Our strength is not in our individual faith, which may be shaken, or even broken, but in our shared vulnerability. We stand together, carrying one another's silence. The tradition does not demand that you go to a quiet corner of your life and say kaddish alone. It demands that we gather together people who care, and who value what it means to remember as a Jew. People who can speak and listen, hurt and comfort, lean on and support one another.
And in this room, we will say three prayers that really matter. We will say the yizkor. We will say the El malei Rachamim. And we will say Kaddish.
The Purpose of Memory: The Teachings of the Soul: Judaism offers hope not in escaping the pain, but in understanding the eternity of the soul (Neshama). The soul is not a temporary component. It is not your personality. It is a spark of the Divine, given to us to nurture and grow. but one that we pour our experiences into over time. We fill it, and develop it, with love, truth, with all that is good and right in our lives. Or we darken it, or weaken it with all that is wrong, selfish, unloving or false. The pure soul lives with God. The strengthened soul survives death.
I keep turning to see him, or thinking he is there in his room. We mourn the physical presence, the hands, the voice. But the love poured into the world by our loved ones, and the love that holds them in your memory, that is the essence of their soul. That love is eternal; they still have it, and you still have it. That is known as memory. And it is the kind of remembering that God remembers today as we prayer Yizkor, He will remember. Yizkor, I will remember. Nizkor, we will remember. Hu Yizkor, he remembering is forever and enduring, has he gathers in love the souls of those whom we have lost.
So we will then turn to the El Malei Rachamim: This prayer, which we are about to recite, is the antidote to the coldness of Unetaneh Tokef. Death may come, but they have a future nonetheless. Tachat Kanfei haShekhinah, it is a petition that they find rest beneath the wings of the Divine Presence, no matter how they passed from this world. The entire Yizkor service was a response to the brutality of the crusades. We have el malei rachamim prayers for the 6 million, for the thousand slaughterd on October 7, for the soldiers, saints and martyrs of our people, for those whom this congregation lost in the past year, for our loved ones forever over time.
Unlike the unetaneh tokef, death is the starting point, not an obstacle. It is not about promising life; it is about God promising comfort and everlasting connection. It affirms the soul's unique identity, even as it transitions. We are not just remembering a past life; we are acknowledging an enduring spiritual presence for them as we pray they be bound up in the bonds of life eternal and the bonds of our lives below.
The Talmud later explains that Elisha ben Abuya's error was in not realizing that the promise of "long life" for these mitzvot refers to the World to Come (Olam HaBa), not necessarily a long life in this physical world. Our grief is for our loss, but our prayer is that they are ongoing. That their story may have ended but their life, their being, their love, their memories, their bonds to us and the fabric of reality have not been cut out of the universe. The neshama lives on without the broken body that it left behind. This is the God of mercy we so sorely miss when our beloved are taken from us.
Yom Kippur is the day we fight for life, even after experiencing death. We stand in the conflict between absolute loss and enduring hope. Hope is not optimism; it is the battle that prayer can win. When we open the machzor for Yizkor, I recognize that these words may be hard to say. They are for me. They may be harder than ever before, and they may remain this way for as long as the soul that God breathed into me lives in me. But who ever said meaningful things would always be easy?
So as we turn to our Yizkor service, I invite you to join me and to do three things:
Be Honest: If the words hurt, let them hurt.
Be Vulnerable: Trust that the person next to you can carry your silence.
Be Present: Focus not on the death, but on the love that binds their soul to yours.
And when we do turn to the unetaneh tokef in musaph in a short while, I encourage you to know that teshuvah - returning - returning to them, to God and to your own love and best hopes for your own life, over and over, is needed, even if it hurts. That tefillah - the words that are hard to say - have enough truth in them to survive the other truths that you also know. Both truths are real. And tzedakah - the tangible, measurable response to life known as generosity and justice is always the right response to loss. We don’t curl up into a corner, we reach out and connect.
May our tears be sacred, may our arguments with the text be heard, and may the souls of our beloved, which made our lives worth living, find true and eternal rest. I pray for you to have a g’mar chatimah tovah - a final seal into the books of life, health happiness, purose meaning and prosperity, in the year ahead. Remembering those whom have gone on before us, Let us now rise to say Yizkor.
