Trump vs. T’shuvah: Contrition and the American soul

As we head into Yom Kippur during one of the most dismal elections of our era, there are a few questions this election has led me to ponder.

What is contrition? What is the relationship between contrition and t’shuvah, “repentance”? And what is it about Donald Trump, a man who seems to be incapable of contrition, that so excites his followers? These questions are intertwined, and I want invite the reader to reflect on them together with me.

In Hebrew the word for contrition is “charatah,” and it’s an essential part of doing t’shuvah. Regret for the past, confession in the present, and commitment to make different choices in the future: contrition and t’shuvah can’t be created out of less than these three strands. Together, they weave together time in a new way and create a renewed reality.

That’s what it means to say that t’shuvah changes reality. That’s why in the Jewish view, freedom comes from the power to do t’shuvah, to achieve a state of contrition. That’s why according to Midrash, t’shuvah is the very foundation not just of our humanity, but of Creation itself.

But imagine what contrition feels like to someone who is unable or unwilling to do t’shuvah. The need for t’shuvah then becomes a deferred burden, a judgment against one’s life and one’s contentment. In that state, the only freedom clearly perceived is the freedom to not have to do t’shuvah, to walk away from one’s sins as though they were accidents that happened to you, or as though they never happened at all.

Donald Trump’s repeated declaration that hate speech against women is just locker room banter, without real life consequences, is just that kind of melding of denial and apology – it was the fault of the atmosphere he found himself in, something that happened to him. Of course Trump has an infamously long list of things he might want to apologize for. This was the first one that that he “is not proud of,” because it was the first that threatened his ability to win.

A deeper question is why it’s so important to Trump’s political success to never be contrite. What would seem to most of us to be a great weakness is to his supporters a source of great strength. Why?

Here’s a theory. We live in a country that has some very great sins deeply embedded in its national identity and narrative. Between the enslavement of Africans and the genocide against Native Americans, our country’s wealth and land are the outgrowth of stolen fruit – not just from taking wealth and land belonging to other people, but from squeezing out the juice of their very souls and lives.

In the shade of slavery and genocide, many strange plants bloom, including liberal guilt, political correctness and self-censorship.

This kind of guilt is rooted in a t’shuvah process that is permanently stalled. The guilt arising from incomplete t’shuvah can be debilitating. It can atrophy one’s moral compass and intuitive sense of right and wrong. And it is where so many white liberals find themselves today. Its obverse would be the idea of righteousness we sometimes project onto people who are “not white.”

When there is t’shuvah to be done but one is unable to do it, one’s feeling of guilt comes without a connected feeling of responsibility. One knows there is a problem that needs solving, a past that needs transforming, without feeling empowered to effect that transformation. And these feelings can persist without ever bringing us to the point of real t’shuvah, which would dissolve the residue of guilt.

No wonder so many people who see themselves as politically conservative reject this guilt, and along with it, political correctness and identity politics. On a personal level, I think this feels similar to what it is like to give a forced and insincere apology. Anyone who has had to do that knows it can be spiritually deadening.

But so many people whose ethnic origins are racially “white” reject this guilt for a more basic reason: they see their communities undermined and destroyed by the same processes that bring others great wealth. They do not see themselves as inheritors of the usufruct of slavery and genocide. I can readily imagine how hard it would be in those circumstances to be open to contrition.

There are two ways out of this dilemma: either complete the process of t’shuvah on a national level – meaning reparations and a serious re-evaluation of America’s greatness, or reject the idea that there is anything to do t’shuvah for.

Donald Trump represents the latter choice. That is why he cannot apologize for anything, and that is how he fulfills the id-driven needs of his core supporters. Trump represents the freedom to never be contrite, to never have to do t’shuvah. It is as if the only people who need to do t’shuvah are the people foisting guilt upon the American conscience. This is Trump’s most basic message, his essential character and selling point. 

In the world of Trump’s loyalists, contrition is for the weak, yes, but more importantly, contrition is for people who are enslaved to the past. Freedom in that world is the opposite of contrition. But Jewish teachings tell us the opposite: contrition is not enslavement to the past, but the only way to achieve freedom from the past.

How deep it is that the year of this election is also the year that Columbus Day falls on the day before Yom Kippur. In Northampton MA, where I live, it also happens to be the first year that Columbus Day is being observed as Indigenous Peoples Day. This represents the choice we have before us: honor the enslaved and conquered, or celebrate the conqueror. Similarly, as a nation we have a choice: embrace t’shuvah, or run away from it.

Lest this simply be an indictment of Trump’s most loyal followers, let us recognize that the freedom to be contrite can itself be a kind of privilege. It is our moral inheritance as Jews that gives us the power and wisdom to reach for contrition even in difficult circumstances, whether we find ourselves in circumstances of oppression, or all the more so, when we find ourselves in circumstances of wealth.

The Torah warns us that the freedom that comes with wealth is an obstacle to contrition. This is an important theme of the Torah portion we read right after Yom Kippur. But in America, the Jewish community is doing better than that. In America, with our successes, we still mostly hold to the idea that contrition is true, and good, and a balm to our souls.

The palpable need to not do t’shuvah is how we arrive at Trump, the rich man who speaks for the poor – not for their needs or their dreams, but for their resentment. Beyond any dog whistles and ignorant tweets, this is why Trump stirs up powerful racisms and anti-Semitism – they are ideological reactions against the very idea of guilt and responsibility.

The burden of t’shuvah can be so great as to be unbearable, unless one bears it as a privilege, as we are called to do on Yom Kippur. May we do so with grace.

Rabbi David Seidenberg is the creator of