Empathy For The Devil

Cultivating empathy for loathsome people

I was in my forties when my mother heard that one of my senior partners was being rude to me at work. “He’s just jealous of you,” she said.

My mother was being empathetic. Not with me but with my boss.

The strict definition of empathy is to identify with the emotions, thoughts, or attitudes of another. In that sense, you use empathy as an analytical tool to understand or anticipate another person’s actions.

However, another person’s mind is its own place, so to engage in empathy is always to look through a glass darkly.

In the case of my mother, she knew my boss well and knew his competitiveness and insecurities. So she could make an educated guess about his motivations. She told me that certain aspects of my life and character would forever be beyond my boss’s grasp, that he was aware of this, and, whether he knew it or not, that’s why he was being rude.

Was she right about why my boss was being rude to me? Maybe. Was my mother’s guess highly prejudicial in my favor? Of course, she was my mother. But her explanation was plausible, and I accepted it because it made me feel better.

Her effort at empathy was a story she told me about my boss’s mind.

Empathy as a story but also as a weapon

My brother Samuel is a veteran public defender who now only defends people accused of murder. A trial, Samuel tells me, is not just a battle over the evidence but a battle as well to influence the empathy of the jury. To get the jury to tell themselves a certain story of what happened and what was in the mind of the defendant.

The prosecutor will attempt to shrink the jury’s perception of the defendant solely to the murder they’re accused of, as if that single alleged act constitutes the entirety of the accused’s life. Look inside the defendant’s mind, the prosecution will imply, and all you will see is the mind of a murderer.

The prosecution is trained to refer to the accused as “the defendant.” Samuel will use his client’s name as often as possible.

In conducting his defense, Samuel will try to get the jury to see his client expansively, as a fellow human being with relatable, common, human experiences. His client had a mother who once lovingly, carefully applied a Band Aid to a scraped knee. His client’s older brother taught him to swim. Anything to make the jury see that his client’s life story is far greater than the alleged single worst moment of a life full of countless ordinary human moments.

But empathy can be manipulated only up to a point. Proper empathy is not a fable. When we try to enter the mind of another, we do so knowing certain facts. And facts are stubborn things.

Empathy is not sympathy

Sympathy is an emotion of fellow-feeling. It’s not analytical. It may have nothing to do with facts. When our young children would hurt themselves by bumping into, say a table, I’d sympathize with their tears and ask them to conspire with me in devising a suitable punishment for the offending table: “No TV for you, table. Ever.” Soon, they’d be laughing and joining me in the absurdities.

In contrast, empathy has everything to do with assembling facts in order to analyze someone as best you can. You may choose to highlight or downplay certain facts in order to create a narrative that suits your purposes, similar to what often happens at a trial when attorneys like my brother give their opening and closing remarks to a jury.

Often, however, you want to be as rigorous as possible in your empathetic analysis.

Robert Wright

has called this “Cognitive Empathy” and has used it to game out, for example, what Vladimir Putin or Xi might do in response to various actions by the United States. Using Putin and empathy in the same sentence can strike people as morally wrong unless they understand that empathy is value neutral and not synonymous with sympathy nor inconsistent with loathing Putin. ¹

Empathy and our rogue neighbor

If Putin is guilty of vast and terrible war crimes, our absentee neighbor in East Hampton was guilty only of a minor misdemeanor. But because our neighbor’s actions directly impinged upon us, we loathed him more than we loathed Putin. Proximity will do that.

Our neighbor owned the undeveloped lot next to us. His lot was full of untended brush and had trash around its perimeter. In the course of building a fence on the border between our two lots, one of our contractors cleared a narrow strip of his land.

When we learned of the encroachment, we apologized to our neighbor. When an apology didn’t suffice, we offered him a token settlement, despite having caused no damage. But an apology and some money were not what he was after. A google search revealed that our neighbor was well into his eighties and had a long, sordid history of frivolous lawsuits.

And so he sued us.

Loathing this man was retrograde to our enjoyment of our house. His ugly lot was visible to us every day as a reminder of his bad behavior.

Our goal was to find a way to stop actively loathing him and find another emotion less toxic to us. So, with the limited facts at hand, we used empathy to create a plausible backstory for our neighbor’s motivation.

He had led a sad and lonely life and was so desperate for human contact that he had to resort to lawsuits to achieve it.

That didn’t excuse his behavior or change our low opinion of him. But forming a view of his motivation gave us greater power over our own feelings. Our negative emotion remained, but it was tempered by the story we told ourselves.

I’ve experienced brief bouts of loneliness and have been grateful when they ended. So I could imagine the horror of being old and lonely with no end in sight except the grave. To be clear, this was schadenfreude, not sympathy.

To conclude this tale, when it became apparent that our neighbor would litigate, I raced to hire the top litigation firm in Suffolk County. ²  When our neighbor tried to hire that firm and was told they were already conflicted, he was furious.

As it turned out, the lawyer he did hire was embarrassed about bringing forward such a ridiculous lawsuit––she was going to lose face in front of the Suffolk County judge who would almost certainly rage at her about crazy Hamptons people and their entitled nonsense.   

Time passed, and a filing deadline was missed. The suit was rendered toothless. We still gave the neighbor a token settlement to excise him from our lives.

Our neighbor’s folly became fodder for dinner party conversation about just how ridiculous Hamptons real estate disputes can be. 

The most loved and loathed man in America

The idea for this post was not mine. I met a fellow Substack writer

Julie Gabrielli

via a thread created on

Substack Writers at Work

the excellent writing site of Sarah Fay. For that thread, Sarah asked people to pick a topic that they wanted another writer to tackle. Julie’s topic was “Cultivating empathy for loathsome people.” I picked Julie’s topic because it was timely, important, and challenging.

Julie did not tell me her motivation for her chosen topic. I’m going to play the odds and make an educated guess.

In American life today, the person who seems to command the largest populations of people who either loath or love him is Donald Trump. That’s my guess. And given Julie’s topic I will focus not on Trump lovers but on Trump loathers.

To declare myself, I‘m an anti-loather. Loathing takes a great deal of energy, it doesn’t make me feel good, and I don’t see any positive value in it

I think if you want to defeat loathing, you ought to first consider whether you have agency. Can you use the otherwise wasted heat of your hate for a productive purpose?

If you loathe Trump and don’t want to see him become president again, you do have agency. You can vote, you can volunteer, you can write letters to increase turnout among groups likely to oppose Trump, and, if you can afford to, you can give money to Trump’s likely opponent Joe Biden.  

Of course, if you are in the “love Trump” camp or the “loathe Biden camp,” you can take the reverse actions.

Taking action is likely to make you feel better than stewing in fear and loathing, because it’s a release of energy that’s only making you upset.  

You can also use the analytical tool of empathy to form a backstory from Trump’s biography to explain how he became who he is today.

Here are a few well-established themes to work with.

Donald’s father Fred was a “cold and stiff” tyrant who “pitted his children against one another.” Fred “fueled an ugly rivalry between Donald and [Donald’s brother] Fred Jr.” Donald won the contest for his father’s favor. The more gentle Fred Jr. was driven by his father out of the family business and into a lifetime of drinking that contributed to his death at age forty-two. ³

Donald’s father demonstrated an attitude and a pattern of behavior of acting as if he was above-the-law. Fred serially overestimated his land costs in a publicly funded project, was audited, and then was “shut out of government funding” for his “profiteering.”  Later, both Fred and Donald were sued for “discriminatory rental practices against Black tenants.” ⁴

According to a thorough New York Times investigation, Donald was given a tremendous amount of money by his father at a very early age. Donald was a millionaire by the time he was eight, and was earning the then equivalent of $1 million a year after he graduated from college. Fred’s motivation was to evade inheritance taxes. Fred funneled money to Donald and his siblings using dummy corporations, and at Fred’s death, his estate was severely undervalued. ⁵

Fred also was there to bail out Donald when he got into financial trouble, most famously in buying $3.5 million in casino chips at one of Donald’s failing casinos. ⁶

I see a backstory of a person who is likely to grow up feeling insecure and envious. But also, someone who thinks of himself as extraordinarily entitled, including being above the law.  

When I think of Trump with that analytical lens, he becomes more relatable to me as a human being rather than merely a two-dimensional meme or a monster. Imagining Donald Trump as a child and young man can explain a lot about who he is today.

I’m not offering excuses and not suggesting that anything about Donald Trump’s’ backstory ought to change your opinion of him for better or worse. And I’m certainly not suggesting sympathy.

Rather, I’m suggesting that Cognitive Empathy gives me more mastery over my emotions. It also shifts the power dynamic between me and the object of my analysis. Knowledge is power.

And when you’re using your frontal lobe, which is the analytical part of your brain, then the amygdala, the primitive, emotional, fight or flight part of your brain can be suppressed.⁷

In these ways, I can drain most of the poison from the fangs of my loathing.

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I started this essay thinking that loathing was a release for me. I could wind myself up into a great rage and think all sorts of horrible thoughts about the object of my loathing. I’d disparage the person in extreme ways, think things I’d never give voice to. Struggling with this essay taught me a different point of view. So, thank you Julie Gabrielli.

Joan Didion famously wrote: “We tell ourselves stories to live.”

To put a different spin on her quote, we use empathy to tell ourselves stories to make sense of the people we encounter.  

And that gives us a greater sense of control over our own emotions.

Question For The Comments: I’d love to hear your advice about how you handle loathing.

All paid subscription revenues will be donated by me to The Robin Hood Foundation. Every dollar makes a real difference.

Below: Spock uses the Vulcan mind-meld to achieve the ultimate in empathy.

1. As

Robert Wright

put it, “Please abandon the common assumption that to explain why people do things is to justify their doing those things.” From “How Cognitive Empathy Could Have prevented The Ukraine Crisis”

2. Tony Soprano “taught” me this trick when he raced around to give retainers to all the good local divorce attorneys before Carmella could hire them. (My wife approved this footnote.)

3. Quotes from Maggie Haberman; Confidence Man; 2022

4. Ibid.

5. New York Times Investigation: Trump Engaged in Suspect tax Schemes as he Reaped Riches From His Father; October 2018

This was a serious investigation:

“The findings are based on interviews with Fred Trump’s former employees and advisers and more than 100,000 pages of documents describing the inner workings and immense profitability of his empire. They include documents culled from public sources — mortgages and deeds, probate records, financial disclosure reports, regulatory records and civil court files.

The investigation also draws on tens of thousands of pages of confidential records — bank statements, financial audits, accounting ledgers, cash disbursement reports, invoices and canceled checks. Most notably, the documents include more than 200 tax returns from Fred Trump, his companies and various Trump partnerships and trusts. While the records do not include the president’s personal tax returns and reveal little about his recent business dealings at home and abroad, dozens of corporate, partnership and trust tax returns offer the first public accounting of the income he received for decades from various family enterprises.”

6. The Washington Post; Trump’s Bad Bet: How too much debt drove his biggest casino aground. January 2016

7. My knowledge of the human brain is superficial, and so this is my superficial understanding. For me, engaging in analysis does suppress my emotions.