The Ordinary (and Exceptional) Vices of Trumpian Politics

(repost from Substack: originally published August 12th, 2025)

The Trap of Anti-Hypocrisy

Far from being an amoral free-for-all, liberalism is, in fact, extremely difficult and constraining, far too much so for those who cannot endure contradiction, complexity, diversity, and the risks of freedom.”

-Judith Shklar, Ordinary Vices

In Ordinary Vices Judith Shklar picks up where Montaigne left off. She names “cruelty, hypocrisy, snobbery, betrayal, and misanthropy” as humanity’s “ordinary vices”. But, in both Montaigne’s and Shklar’s opinion, we must rank cruelty the highest of these vices and learn to be more tolerant of the others. In fact, it is our obsessive repulsion toward hypocrisy that we should be suspicious of.

In the London Review of Books, Bernard Williams says of Shklar, “Because she puts cruelty first and fears misanthropy, she distrusts the special hatred that much modern feeling reserves for hypocrisy.” At a later essay I will explore her assertion that cruelty is the worst vice in more detail. But, today I want to focus on how our prizing of authenticity above all, has paved the way for Trumpian politics of cruelty.

In her essay: “Let Us Not Be Hypocritical” Shklar opens the first few lines saying, “Hypocrisy remains the only unforgivable sin among those who can overlook and explain away every other vice.” She goes on to say,

“Puritans are inherently prone to hypocrisy and antihypocrisy…They suffer from an inner tug of war as intense as the perpetual accusations they thrust at others, because they are terrified of their own weakness and suspicious of their neighbor’s lapses.”

What Shklar gets at here is how the anti-hypocrisy cause (and its propensity to become hypocrisy) is rooted in our oldest traditions - particularly, in Judeo-Christian culture. In John 8:7 Jesus says, “he who is without sin, cast the first stone.” The story of Jesus defending the woman who committed adultery and was thus condemned to death by stoning, is typically heralded as a shining example of Christian mercy and forgiveness. It is so much so, that in our cultural zeitgeist, the english idiom “cast the first stone” means to “act self-righteously in accusing another person, believing oneself to be blameless.” While it is undoubtedly noble to ask people to reflect on the ambiguity of their own morals, there is a hypocrisy in Jesus’ anti-hypocrisy. He is showing mercy to a first time offender as an act of Christian goodness. He is not however, saying that this is an abhorrent system of justice that is paradoxically meant to punish sin while also producing it.

The passage concludes with: “go, and sin no more”. It’s not a request: it’s a command. It is worthy to wonder, what should happen if she sins again? Is she now deserving of the stoning? I would argue that cruelty and public humiliation are unacceptable remedies because they are inhumane; further, that prescribing brutality as a punishment for wrongdoing will only lead to more cruelty. It poisons the soul of both the receiver and the giver. It is impossible to see an objectively proportionate response when one is the object of another’s cruelty. It’s dehumanization colors all passions. As Shklar notes: “Cruelty is a vice that transfigures human characters.”

We are left asking - is the true crime a society that is not consistent in its condemnation of sin or, a society that would punish its sinners with cruelty?

It is easy to see the foibles and hypocrisy of Puritanical zeal in the religious; it is harder to see it in ourselves.

Think of the particular hatred we have in our hearts for this stock character: the ultra-conservative politician, who denounces homosexuality and enacts laws criminalizing it - whilst simultaneously engaging in sexual dalliances with anonymous young men. It is this politician, more than all others who support the anti-gay agenda, that we seek to humiliate and destroy. There’s a deep satisfaction in exposing blatant hypocrisy. But, I wonder if it is right to place more blame on this avatar for hypocrisy than on the systemic cruelty of the anti-gay position. There are many other homophobes in positions of power with no stain on the legitimacy of their prejudice. Are they more respectable?

We view the closeted politician as a worse person because he knows he is lying to the world. Therefore, he should operate from a place of greater morality. In ignoring the enlightenment his contradictions should produce, he is breaking our social contract of reason. In this hierarchy of vices, our news cycle turns from focusing on the cause of Gay Rights into focusing on destroying this single enemy. It seems for a moment, as though publicly stoning this one man will eradicate the hate he perpetuates. The dishonesty of the man is bad, but it is the homophobic system he holds up which should be the cause of our greatest scorn.

This tendency towards criminalizing hypocrisy, rather than the obstruction of justice in the court of public opinion, sates our desire for instant gratification. How personally vindicating a viral TikTok contrasting Marco Rubio’s statements pre-and post his pro-Trump conversion is to the viewer. How entertaining it is to bask in superiority. But what do we do with our discovery? It seems right we use it as a means to connect to those who think differently. However, that would cause us to, in pointing out the hypocrisy of the politician, to show compassion to the constituent who bought his bullshit. But patience is hardly algorithm fodder.

The question I’m concerned with is not “is anti-hypocrisy bad?” Addressing hypocritical action, especially in the levers of power in the state, is a useful rhetorical device to draw attention to the argument. It can speak truth to power. But, the question I find more pressing is: “should anti-hypocrisy be the end goal?” Does the winning the logos of the argument win you a better world? If you took a scroll through social media, you would think the answer is certainly, “yes!” But, maybe the fact that it is such an easy and instantly satisfying crusade, evidences how it is not as rewarding in changing our national character.

The key is that to any argument that employs anti-hypocrisy in its rhetoric is to condemn how hypocrisy animates the system toward injustice rather than making the enemy any single example of hypocrisy. How the system treats its people is its societal worth - and, if those who make up the political machine use insincere rhetoric (hypocrisy) to substantiate the value of cruel legislation (say taking food stamps from poor children), then the rhetoric must be addressed.

We are a nation built from the fable of George Washington’s Cherry Tree. The American ideal is bound up with the idea of a Dickensian moral consistency and antipathy for lying. Yet, when we look at any major progress that happens in the country or the world - although we would prefer it happens with moral purity - it never does. In summing up Shklar’s perspective, Williams states, “those who denounced the insincerities of Victorian capitalism probably did less, in doing that, to alleviate its horrors than the liberal reformers who had their own styles of insincerity.” Look no further than Dickens who did more than almost anyone in his activism for England’s poor, but also conducted a surveillance campaign of the “fallen women” at his Urania Cottage.

Let’s bring such insincerity closer to home. Lincoln spouted racist rhetoric, but his mastery of professional politics led to the end of slavery in the US. FDR’s New Deal, that progressives tout as a success toward the “general welfare”, was passed with the help of Southern Democrats by killing anti-lynching laws. MLK is the “ostentatious hypocrite”: a man of god and moral standing who conducted a number of extramarital affairs.

Does the personal hypocrisy of those who enact progress, negate that any progress was made?

To believe such an idea is to give in to misanthropy. If the scourge of hypocrisy is the truest evil and you see it everywhere - as is easy to do since it exists in all of us - then it is likely you will decide humanity is hopeless. But to do so, would be cruel. Because cruelty is turning your back on the helpless, while the powerful strip them of their dignity.

How does all of this relate to Trumpian politics? Williams provides the clarity for that: “[Shklar] explores, as Hegel did, the modern virtue of sincerity: in particular, a sincerity which, in the absence of agreed ethical standards, may dangerously take on the role of providing the ethical standard all by itself.”

To translate: one can be sincerely cruel. If sincerity is of greater value than ethical action, then there is no separation between benevolence and malevolence so long as it is performed with consistency. When hypocrisy is loathed and the appearance of authenticity prized above all, sincerely cruel people can thrive. As Shklar goes on to say, “Tyrants are the personification of all the illusions that accompany domination.” When people talk about what they like about Trump, they frequently are actually stating what they hate in other politicians: that they seem inauthentic, use overly manicured jargon, say one thing and act another. Whereas in Trump - you get what you see. He is a brute in both his words and his behavior. This consistency is posited as the antidote to a system rife with unfairness and hypocrisy.

Others might say, “of course Trump is a hypocrite, 15 years ago he was a pro-choice Democrat.” But, to see it through a Black & White policy lens misses the way the attention economy digests information. In each moment that he speaks Trump seems “present”. Few could ever hear Trump speak and say, “that sounds overly prepared.” It is improvisation at the national level. Perhaps what he says directly contradicts what he stated a week ago, but he never seems as though he himself doesn’t believe the reformed truth. To borrow a line from George Costanza: “It’s not a lie if you believe it.”

In a world driven by artificial technologies and media, where everything is suspect, Trump is consistent. His first priority is now and always has been Trump. He is the opposite of the Dickensian hypocrite, the worst of all sinners.

It’s refreshing to see someone so brazen. It also makes the false equivalency of hypocrisy and outright cruelty. Our social media environment turns the world into a cast of two dimensional characters. This consistency of extremes causes us to desensitize to what should be outrageous cruelty. Why even bother to get angry? That’s just who they are. Better to mock their hypocrisy than engage with the irredeemable. But, then we all descend into madness. If one does not weep for Laken Riley appropriately, any legitimacy they have in weeping for an undocumented mother and her child undergoing cancer treatment falls on deaf ears. And vice versa. To be a fraud is a worse crime than to be an perfect sinner.

Ezra Klein illustrated the dangers of cruelty at the highest level and how it infects our national character:

The White House X Account [posted] immigration ASMR…they were shaking and dragging the manacles they are using when they deport people. It was the ASMR of deporting immigrants as their metal manacles jingle…even if you want to deport people, [the people exalting in the cruelty] are not good people…The cruelty is the point. Virtue matters…and when you walk down this road with yourself, when you begin to wring the virtue out of yourself…you begin to make cruelty a meme, a thing you do for the applause of the crowd.”

Too much is done for applause and too little is done for the collective soul of our Democracy. Of course I am a hypocrite too. At times in my life, I made railing against the hypocrisy of my political enemies my goal. I believed winning the debate would win me the change I believed in. I didn’t understand that change required more patience than reason.

But, that’s life. We shouldn’t distance ourselves from every past inconsistency because that is what it is to be human. The best lesson when we realize it is human to be problematically variable, is that we should not judge it so harshly in others.

As Oscar Wilde said, “We are never more true to ourselves than when we are inconsistent.” Perhaps it is good to aspire to a higher ideal than our actions can ever merit. The fear of playing the fool through “virtue signaling” should never be more potent than the fear of doing nothing at all.

I ask that mankind risks virtue signaling over abandoning virtue altogether.