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Tuesday, September 2, 2025

[Updated] The Trumpiest High Holidays Confessional Ever

In This Moment: A Rabbi's Notebook
[Updated] The Trumpiest High Holidays Confessional Ever
On the Days of Awe, Jews confess their sins and the community's. Therefore it is entirely appropriate to see how many boxes Donald Trump checks in the confessional prayer. Spoiler - it's all of them.
Rabbi Joshua Hammerman
Sep 02, 2025

Best wishes for a sweet 5786. For the new year, or just for the heck of it, send your loved ones the perfect gift for this most fiercely urgent Jewish now - a subscription (free or paid) to In This Moment.

  • As we head down the home stretch toward the new year, I am updating a piece I wrote just before the 2024 election, coinciding with last High Holidays. While rabbis are expected to be “non-political” in addressing their congregations, it is impossible to ignore the moral apocalypse of the Trump era and the ethical toxic waste landfill that is Trump himself.1 As you head into your private reflections this month (if you observe), bookmark this list and share it, not simply to compare your misdeeds to DJT’s, but as a reminder that part of our task in restoring goodness to the world is to fight against the manifold lethal threats of this administration. WE CANNOT FORGET. WE CANNOT NORMALIZE WHAT IS HAPPENING TO US. In that way, we can help restore goodness to America.

    The Yom Kippur / Donald Trump Confessional

On Yom Kippur, echoing the ancient practice of the High Priest in Jerusalem, Jews confess for their own sins, as well as for the community and the Jewish people. The repeated recitation of this confessional actually begins during the month prior to the new year - every morning by Sephardic Jews,2 and during the final week prior to Rosh Hashanah for others.

Since biblical times, it was the leaders who led set the example by leading the people in confessing, prophets, priests and kings, and later, rabbis, all expressed their humility in this way. Most dramatically, King David confessed for his great sin of adultery with Bathsheba, and the subsequent cover up that involved the murder of her husband Uriah. Back in the day, leaders took responsibility for even the most heinous sins.

We can confess Donald Trump’s sins because he sure ‘aint confessing for anything himself, and doing so helps to raise our awareness of what’s at stake in this presidency.

If he truly is mindful of his mortality these days and wants to “get to heaven,” as he puts it, he might consider starting with this list.

He said recently, "I wanna try and get to heaven if possible. I'm hearing I'm not doing well. I am really at the bottom of the totem pole.”

That is an understatement.

It is noteworthy how many from this traditional list of sins known as Ashamnu were committed by just this one man. Spoiler alert: All of them - and I’m primarily drawing from past misdeeds; there are so many going on as we speak, only some of which are known to the public. And that’s not even including what’s in the Epstein files, which I hear are kept in a lockbox waiting for Trump’s arrival at the Pearly Gates, since he’s so concerned about heaven suddenly. To keep up to date on Trump’s most recent sins, click on these links:

So after you’ve completed your own private confession during these days of repentance (and non-Jews are free to partake too), take a moment - OK it will take a few moments - to look at the Viddui confessional below to see how many boxes Donald Trump checks.

Below is the full Hebrew passage - a list of sins recited alphabetically - plus an acrostic English translation. Then we’ll look at them one at a time.

The “Ashamnu,” or “Short Confessional,” alphabetical list of sins
Source: Machzor Lev Shalem

You can recite them each day during this month, and then, as custom dictates, listen to the sound of the shofar each day as we count down the days to the new year.

Now, for your convenience, I present a fully annotated Trump confessional. As you read these sins, you may want to follow the tradition of tapping your chest as a means of awakening the heart, sort of a spiritual defibrillation dramatizing the life-and-death importance of sincere repentance.

The Trump Ashamnu Prayer - Source: Open Siddur

Somewhat fittingly, the Hebrew word for guilty, from which the term Ashamnu comes, is Uh-shame. The Talmud states that we are all interconnected. In that way, DJT has brought great shame and embarrassment not only to himself, but to the American people. See below this view from abroad. Not too many former US Presidents have been noted as convicted felons in the international press. Come to think of it, just one. THIS CAN NEVER BECOME NORMALIZED. (2025 update: It has been - though the Scottish newspaper shown below did a nice job recently)

“Stolen” is a rather mild term. Below is the lexicon definition of the Hebrew root G-Z-L. Trump has ripped away freedoms and rights that were in place for half a century. This abduction can only be undone at the ballot box - and even then, so much damage can never be undone.

Dofi means blemish or fault. Dibarnu Dofi means “we have spoken slander,” but with the implication that we are looking to find fault… - Rabbi Debra Orenstein

He’evinu comes from the Hebrew root a.v.n. meaning trouble, sorrow, or suffering, as well as sin, wickedness, or idolatry. This verb is in the causative form: we have caused avon. Sometimes, it is translated as “we have acted perversely” or “we have caused perversion,” because of the deliberate nature of avon. Ish avon in the Bible is a trouble-maker or noxious person. - Rabbi Debra Orenstein

Vehirshanu - The Hebrew word ra is usually translated as evil or wickedness, but it can also mean harm. This verb is the causative form, meaning “we have caused evil and/or harm.” How have I caused harm this year – by omission and commission, willfully and accidentally, to those close to me and to strangers? - Rabbi Deborah Orenstein

  • Fact check: Six days of Trump lies about the Hurricane Helene response (CNN) Trump’s deliberate misinformation campaign caused immeasurable harm to victims in need of government support (which was available to them). It reminds us of the harm he inflicted on the American people through misinformation he spread about Covid during his first term in office - and what he is doing to undermine medical science now.

Zadnu means to behave arrogantly, proudly, or presumptuously. It comes from a root which also means to boil or to seethe. We think, in English metaphors, of seething or boiling over with anger, but in the biblical image we seethe or boil over with pride, which may lead to anger. What is boiling up inside me? - Rabbi Debra Orenstein

Check out this usage of the term in Psalm 19:13 (19:14 in the Hebrew text), and then these other verses from Psalms (see below)

“Let the arrogant not rule over me.” Amen!

Psalm 119 also references the arrogant, using this very term - zedim - six times. Trump has lied, shamed, slandered, derided and otherwise defamed Jews at least that many times. Personally, I got my head examined and came out chanting this psalm.

21 You rebuke the arrogant, the cursed, Who wander from Your commandments.

51 The arrogant utterly deride me, Yet I do not turn aside from Your law.

69 The arrogant have forged a lie against me; With all my heart I will observe Your precepts.

78 May the arrogant be ashamed, for they subvert me with a lie; But I shall meditate on Your precepts.

85 The arrogant have dug pits for me, those who are not in accord with Your law.

122 Be surety for Your servant for good; Do not let the arrogant oppress me.

There is no etymological connection between Hamas the terror group and the biblical term hamas, found here, which refers to gratuitous, lawless violence in chapter 6 of Genesis, at which point God decides to bring a flood to destroy Creation. In Arabic the word Hamas is an acronym for “Islamic Resistance Movement” and also connotes zeal. As for Trump, a zeal for violence has been a hallmark of his leadership. While I am not focusing on the heartbreaking situation in Gaza in this posting - including Israeli culpability - it is clear that Trump has enabled the worst, most extreme right-wing, Putinesque forces to prevail, both within the Israeli government and around the world. Trumpian sins of “diplomacy” have cost tens of thousands of lives, in Ukraine, Gaza and elsewhere.

Tafalnu sheker means “we have smeared with lies” (see Psalms 119:69). The Hebrew root T.F.L. can mean to smear or plaster over. So we are alluding to lies that don’t just contradict the truth, but attempt to cover up the lie or smother that truth. - Rabbi Debra Orenstein

That sounds a lot like the Big Lie theory (the große Lüge) articulated by Adolf Hitler. The historian Zachary Jonathan Jacobson wrote about it in The Washington Post a few years ago:

Adolf Hitler first defined the Big Lie as a deviant tool wielded by Viennese Jews to discredit the Germans’ deportment in World War I. Yet, in tragically ironic fashion, it was Hitler and his Nazi regime that actually employed the mendacious strategy. In an effort to rewrite history and blame European Jews for Germany’s defeat in World War I, Hitler and his propaganda minister accused them of profiting from the war, consorting with foreign powers and “war shirking” (avoiding conscription). Jews, Hitler contended, were the weak underbelly of the Weimer state that exposed the loyal and true German population to catastrophic collapse. To sell this narrative, Joseph Goebbels insisted “all effective propaganda must be limited to a very few points and must harp on these in slogans until the last member of the public understands.”

Ya’atznu Ra means we’ve given bad advice, or egged someone on to do something destructive. Like, say, speaking waaay out of line as a private citizen to encourage the Israelis to bomb Iran’s nukes, which Trump recently did, and presumably wanting to foment chaos before the election. He’ll do anything to foment chaos, like, say, commit impeachable offenses by blackmailing the leader of Ukraine in a perfectly corrupt phone call. His “advice” to Republican lawmakers to shun the compromise border bill (favored by many conservatives) was also transparently self serving and horrible advice. It’s the quintessential Ya’atznu Ra moment of this campaign.

Trump’s First Impeachment: The short, medium and long story (BBC)

Kizavnu means “we lied” or “we were false.” Its most famous use in the Bible is in Psalms 116:11: kol ha’adam kozev, “Everyone is false.” The literal translation of that verse is: the whole person is false. Most of us don’t lie on the witness stand or perpetrate other heinous falsehoods. Nevertheless, there is a way in which, for each of us, our whole personhood is false. So often, we are simply fake. We try to please people by saying what we think they want to hear. In the name of protecting ourselves, we fail to be true to ourselves or fully honest with others. It’s time to admit that this “protection” is hurting more than helping. Most people see through our masks anyway. God knows all. Falsehood wears on the soul. That may be why the noun form of the root k.z.v. means disappointing, as well as deceptive. The reflexive verbal form also means to disappoint. Truth is God’s seal – and a better way. - Rabbi Debra Orenstein

Trump is perhaps the most perfect example of a Kozev on this planet. A fake person, one without a moral core, so he is free to say anything at any time and never mean it. Just ask him his position on abortion. Then ask again in a few hours.

Latznu - means to mock. Mockery seems to be the sum total of Trump’s repertoire of humor. He seems to enjoy mocking those with disabilities, or the elderly - though that now might hit too close to home. His form of mockery often looks like projection, such as when he questions an opponents physical strength or intelligence. He doesn’t just mock opponents. He mocks his own supporters too.

In the Bible, a mered can be both a political rebellion and a spiritual tussle with God. It’s mentioned only once, in Joshua, but post biblically, the word is significant in Jewish history. The first revolt against Rome (66-70 CE) is called “ha-Mered ha-G’dola,” the Great Revolt,” which was followed 60 years later by “Mered Bar Kochba,” the Bar Kochba Revolt. The Warsaw Ghetto Uprising was also a mered. All of these arguably were heroic and good, though ill-fated. In modern Hebrew, a mered is a mutiny or insurrection, and the root M-R-D has ties to the Proto Semitic marad: to set up a resistance, to escape, to separate from the group, to leave one’s people. All these terms have a common thread of defiance and divisiveness.

While we often romanticize rebels, Donald Trump is no Mordechai Anielewicz. He is not a rebel with or without a cause, so much as a crybaby without a cookie. The fact that he occupied the same office as such rebels and dreamers as George Washington, Abraham Lincoln and FDR is where the similarity ends. Steve Jobs’ salute to “The Crazy Ones” was speaking about a whole different brand of crazy.

Trump is a rebel because he led an insurrection, a defiant and divisive one. This was no Warsaw Ghetto Uprising. People who romanticize him because he breaks things need to remember that America really appreciates those who build things.

Niatznu connotes a lack of respect, a contempt. The term means “to taunt” or “to scorn” in Hebrew. But blasphemy works here too. When you think about how Trump has treated God like just another prop, like the American flag he hugs. For him, literally, nothing is sacred, for he holds no other Lord before himself.

Where maradnu is a decisive, often violent political act of separation, sararnu connote stubbornness. The most well-known example of this word in the Bible (and only usage in the Torah) is the stubborn and rebellious child in Deut. 21. It doesn’t end well for him in the Torah - the rebellious child is to be stoned to death. “Thus you will sweep out evil from your midst: all Israel will hear and be afraid.” And may I add, be very afraid. In real life such a punishment never happened, but the idea is that such unhinged obstinance must be controlled and tempered.

Trump’s stubbornness is expressed in his proven inability to grow from mistakes and own up to them. He will never admit when he’s wrong, even when the mistake is trivial, like drawing an incorrect path of a hurricane. It’s a tragic flaw for anyone, but especially so for leaders. There is a very short distance from laughable anecdotes to Big Lies.

Avinu (and the next one, Pashanu) - In the Bible, the word avon refers to three things: iniquity, guilt for iniquity, and punishment for iniquity. The illusion or miscalculation of the sinner in the crucial moment of choice is that s/he can derive immediate gratification from the sin, but avoid guilt and punishment, or postpone them indefinitely. It is built into Biblical Hebrew that iniquity cannot be separated from its consequences. Pashanu means “we have transgressed,” and it implies a serious transgression. In modern Hebrew, one translation is “felony.” Like avon, pesha refers not just to the sin itself, but to the guilt or punishment that follows from it. Pesha can even refer to a sacrifice made in atonement for a transgression, letting us know that repentance is intimately tied up with sin, and that sin holds the seed of repentance in it. - Rabbi Debra Orenstein

If the seed of repentance is in the sin, there can be no redemption where there is no recognition of error.

I checked to find examples of when Trump admitted to a mistake.

Tzararnu - Meaning, “I was hostile, adversarial.” The Hebrew root TZ-R-R is the same for the word “narrow.” “I called to God from the narrow place (mei-TZAR) - Psalm 118. Egypt (Mitzrayim), Israel’s ultimate place of restriction, is spelled with those same letters.

What does a hostile person do? They avenge their psychic wounds by restricting the freedoms of their opponent. Trump has already done that with his judicial picks, and he wants to do more. Tzar is also “trouble.” Specifically in the plural, because trouble always comes in bunches - the word is tzarot. In Yiddish, tzuris.

When God calls Israel a stiff-necked people, it almost seems like a compliment, however begrudging. But it is used as God’s reason for wanting to abandon them. We’re stubborn, refusing to respond to commands, like recalcitrant livestock. We aren’t impulse obeyers. We’re repeat offenders.

I’ve come to see the stiff-neck brand is one that serves the Jewish people well. One might say that even Moses did, in Exodus 34:9, where the people’s stiff-necked status is cited as a reason for God to remain with them. If the challenges of life are to be met by a stubborn resolve, that gumption originates in the part of the body where we swallow hard, that unguarded spot most vulnerable to the spear's thrust, the batter's foul tip - and, as we saw with George Floyd - the knee's plunge.  We all need to develop a thick skin - but more than that, a stiff neck.

Proverbs 29:1 explains why and when stiff-neckedness is detrimental - when it doesn’t stop. Someone who is, after repeated warnings, still unable to overcome the stubborn resistance to change, will suddenly be broken beyond repair. It gets to the issue of how reproof should be delivered and accepted in Jewish tradition. Maturity is marked by not only accepting correctives, but loving it.

Trump’s stiff neck will not allow him to turn around and see the damage he has caused, the ruins behind him. He will never change, at least not for the better, which is why we can only assume past will always be prologue for him - as we’ve discovered time and time again in his second term.

Rasha is not just “bad.” Traffic on the West Side Highway is bad. The Colorado Rockies are bad. But if in Hebrew you call someone a Rasha, don’t expect a new year’s card next Rosh Hashanah. To be called a Rasha puts you in the seventh circle of Jewish hell. Haman’s full name is traditionally, Haman Ha-Rasha. Haman the Evil One. One month after Purim, the second child at the seder is called “Rasha,” although we’ve tried to matza-wash him or her. Hey, I’ve even tried to whitewash Haman, saying he was misunderstood.

So on Yom Kippur, we are all confessing, collectively but also individually, to being Rasha. That is incredible, when you think of it - and accounts for a good deal of the reason so many Jews are in therapy.

We’re not really as bad as Haman. But we are all capable of inflicting a world of trouble on this planet, either through our action or our inaction. We need to recognize our limitless potential for evil - and good.

Donald Trump is incapable of doing that. Otherwise, he would not bring such pain to so many people, even as we speak, with his crazy accusations.

Shichatnu In this causative form, the root s.h.t. means to ruin, destroy, spoil, corrupt or pervert. Proverbs 6:32 is a prime example: “Whoever commits adultery lacks understanding (chasar lev). Anyone who does so perverts/corrupts/destroys his soul.” - Rabbi Debra Orenstein

We could go into depth on Trump’s attitude toward women here. Also, interestingly, Jewish environmental laws are collected under the rubric of bal tashchit, “Do not destroy,” which also comes from that same Hebrew root. So as we beat our chests for that one, we should all say an extra prayer for the US southeast this weekend, and think of how we all have contributed to this overheated world that we live in.

Trump’s environmental sins are being shortchanged during this campaign, for whatever reason. It doesn’t mean we should ignore the fact that his reelection has become an existential threat to our planet.

Here’s what his first term brought.

And now he is gutting our environmental protections. Just for spite. Talk about derangement syndrome.

The Torah considers certain sins to fall under the category of “abominations.” Frankly, standards change as to what they are, but the main point is that they are serious. Like Rasha above, Yom Kippur lets no one off the hook. What ever it is that human beings are capable of doing wrong, we’ve done it. Or at least someone has done it, and we’re collectively responsible.

But it’s not just the deeds, it’s how and why they are done. The Hebrew root here comes for the expression for desire and lust. See the Bible Hub analysis below:

Trump is impulsive beyond repair; the Access Hollywood tape and lurid details of his treatment of women over the decades indicate that he is a prisoner to his lust, his greed, his appetite, his …well, if there were an eighth deadly sin, he’d be guilty of that one too. And that’s before we’ve seen the Epstein files!

Ta’ainu means “we have erred” or “we have wandered.” When Hagar wanders in the desert, physically and spiritually lost, this is the Hebrew root that describes her movement (Genesis 21:14). - Rabbi Debra Orenstein

We are adrift right now in our country. That accounts for the pervasive pessimism that surrounds us, something that Trump tries to feed into. We can’t let him. It’s not easy to be hopeful with so many things dragging us down. But some things are lifting us up too. We need to find our way home. And to find joy in the journey.

We need to recognize that everyone is watching us. Not in a Big Brother kind of way (well, that too), but that we have the potential to lift others up even as we lift ourselves. History has its eyes on us. Trump’s greatest sin perhaps is that he turned people against each other and against their country and democracy, all for selfish ends. All because of his inability to accept his losses. He forced his failures to become our failures. He dragged us down to his fate.

Worst of all, he’s achieving the prime goal of a fascist leader - America and Trump are becoming synonymous, in the eyes of the world and in our own. We have to fight that. We have to wave American flags in defiance of that - everywhere and all the time.

It remains to be seen whether we will be able to dig ourselves out of this morass. But this is the time of year to gird ourselves and find that source of strength, courage and joy to get us through.

My best wishes for a sweet new year and may we all be sealed in the Book of Life.

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1

Click for a complete list of atrocities during Trump’s first term. And here’s a short list of Trump’s immoral and corrupt history:

  • Falsifying medical records to avoid the Vietnam draft;

  • Spitefully attacking decorated war veterans and Gold Star families;

  • Mocking the testimony of sex-assault survivor, Dr. Christine Blasey Ford;

  • Praising, siding with, and declaring his “love” for known murderers, war criminals, dictators, and enemies of the US, including those who actively imprison and murder Christians;

  • Deporting non-white service members of the US Armed Forces;

  • Abandoning US allies in Northern Syria in preparation for a Russian invasion;

  • Attempting to discredit and undermine US intelligence agencies, including the FBI and CIA;

  • Committing adultery with porn stars and Playboy Playmates;

  • Paying hush money to his mistresses in order to conceal his adulterous affairs;

  • Settling a $25 million class action lawsuit over his fraudulent Trump University;

  • Dissolving the Donald J. Trump Foundation by court order for bribery, links to foreign countries, and using charitable funds for paying off personal debt and political campaigns;

  • Being court ordered to pay $2 million for using charitable donations for personal purposes;

  • Having lost 38 lawsuits regarding breaches of contract, defamation, and sexual harassment;

  • Having had over 36 tax liens against Trump properties for nonpayment of taxes;

  • Having businesses and properties linked to domestic and foreign organized crime rings;

  • Labelling desperate Mexican women and children as rapists and drug dealers;

  • Labelling desperate women and children refugees as dangerous terrorists;

  • Labelling Africans and Haitians as HIV-infected people from “shithole” countries;

  • Separating infants, toddlers, and young children from their immigrant parents;

  • Deliberately stoking cruel paranoia and xenophobia about blacks, immigrants, and Muslims;

  • Bullying and making fun of the physically handicapped;

  • Tactlessly provoking military and economic tension with foreign countries;

  • Harming farmers and the US economy with unnecessary tariffs;

  • Declaring any journalist, news report, or news agency that criticizes him as illegitimate;

  • Banning or restricting Muslim immigrants and refugees from entering the United States;

  • Making disparaging, misogynistic, and racist statements about women and racial minorities;

  • Spreading sensationalistic propaganda and false conspiracy theories about his opponents;

  • Publicly questioning the legitimacy of any federal prosecutor or judge who opposes him;

  • Routinely hinting at his desire to eliminate government checks and balances and to remain in office indefinitely;

  • Refusing to denounce white supremacist groups and leaders who endorse him;

  • Calling members of a white supremacist faction “very fine people”;

  • Inciting violence and hatred at his rallies;

  • Refusing to denounce his supporters who perpetrate horrendous crimes in his name;

  • Telling his supporters that he will pay for their legal expenses if they assault other Americans;

  • Encouraging law enforcement personnel to engage in abuses of power;

  • Impeding disaster relief aid to Americans living in Puerto Rico and California;

  • Contributing to the increase in white supremacy, anti-Semitism, and Islamophobia;

  • Frequently appointing white supremacists and their sympathizers to positions of power;

  • Frequently appointing people with gross inexperience or conflicts of interest;

  • Frequently appointing uncredentialed family members and close friends;

  • Compulsively pronouncing over 13,435 false or misleading statements in under 3 years;

  • Using his presidency to promote Trump brands, resorts, and Trump family merchandise;

  • Repeatedly violating the Emoluments Clause of the Constitution;

  • Repeatedly sponsoring and supporting those who violated the House Ethics Committee;

  • Publicly endorsing Roy Moore, an accused child molester;

  • Seeking foreign interference in America’s political campaigns;

  • Having well-documented ties to Russian officials, suggesting collusion with foreign countries;

  • Bribing and extorting the President of Ukraine for personal political reasons by withholding Congressionally-mandated military aid to the country;

  • Having officially been accused of committing a crime by the Government Accountability Office for violating the Impoundment Control Act;

  • Engaging in a cover up about his bribing the Ukrainian President, resulting in his impeachment;

  • Hiding tax returns from public and criminal inspection;

  • Bragging about never paying taxes like other hard-working Americans;

  • Taking measurable steps to oppose and suppress the rights of LGBTQ+ Americans;

  • Taking measurable steps to restrict the rights and protections of labor workers;

  • Taking measurable steps to harm the environment and endangered species, including denying the validity of climate science;

  • Slashing funding for mental health, public housing, and children’s food programs;

  • Disclosing confidential information about Twitter users and whistleblowers;

  • Receiving several reprimands from the Office of Government Ethics;

  • Removing and violating White House ethics training for department members;

  • Being the subject of or involved in 12 congressional investigations, 10 federal criminal investigations, and 8 state and local criminal investigations;

  • Engaging in witness tampering, obstructionist behavior, and witness intimidation;

  • Being pathologically unrepentant and unremorseful about any of his sinful behavior.

2

The Sephardic penitential prayers (Selichot), recited early each morning for the month prior to the new year, is extensive. (See an example here)

3

From the Encyclopedia of Jewish Prayer

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