It’s not easy complaining about America’s political leadership today. There are so many faults to choose from.
I feel only love towards the supporters of President Trump and New York City’s Mayor Mamdani, but the politicians themselves I find wanting.[i]
These are two men pandering to distinct political constituencies. What can we learn from them about what to look for in political leaders when we decide on our vote?
At first, I thought policy might matter most. But despite disagreeing with each of them frequently, I also agree with each of them on many matters including:
Make childcare more affordable: this brings joy to working parents and boosts economic output.
Increase defense spending: in a free world desperately dependent on American leadership, I judge the greater risk to be underfunding.
Clear red tape from small businesses: as an entrepreneur I can attest that’s absolutely worth doing; and then some.
The executive branch should be free to reduce its workforce en masse to increase performance: most organizations perform better as leaner operations.
Perhaps then, what I dislike is their style. And dislike it I do: Camera-loving, video-making, crisis-sparking, constantly-talking, social media vomit. Not my style.
But styles alone do not a good or bad leader make. FDR embraced radio mass media to protect democracy and economically uplift millions of broken-hearted Americans. Mass-murdering strongmen like Saddam Hussein or Joseph Stalin, on the other hand, have hidden themselves and their crimes from cameras.
The defects that upset me about Trump and Mamdani are neither policy- nor style-related.
What stands out is what they choose to communicate to the public. This was especially evident during each of their performative solemn declarations the last couple weeks.
Trump spoke about the 2020 election, insisting on widespread fraud and election interference, ignoring the dozens of independent courts and review processes that confirmed his loss. Mamdani disparaged the democratically-elected leader of a foreign country, Benjamin Netanyahu, for his response to Hamas’s October 7th invasion of and massacre in Israel.
What they talked about reveals two commonalities:
Talking about subjects on which you are far from an expert.
Talking about subjects that don’t relate to your leadership responsibilities.
Consider their lack of expertise:
Trump has no expertise in administering elections. He’s never worked for the Elections Division of the Secretary of State of Georgia. Nor has he served in the Commonwealth of Pennsylvania’s Department of State. He has never worked for the Superior Courts of Arizona or the district courts of Michigan, each of which found no evidence of election fraud.
Mamdani has never lived in Israel or under Hamas or the Palestinian Authority. He is a New Yorker, the son of academics, who grew up in the left-wing Columbia University academic bubble.[ii] Mamdani fits the mold of hundreds of Americans I have met who know vastly less about Middle East history than I do and yet project extreme confidence in their wisdom—to the detriment of the people who actually live there. I only learn new things from Israelis and Palestinians themselves. Which makes sense, because they actually live there.
Consider each leader’s lack of relevant authority:
The 2020 election is over and decided. The Secretaries of State of the relevant states and the courts made the relevant decisions. What the American people need from their President is not what those bodies already do. It’s to protect the United States from foreign adversaries and keep the country free, united, and prosperous.
The war in the Levant has been raging continuously since the 1929 Hebron massacre (and longer). It is irrelevant to the people of New York City. Moreover, the mayor is actually not required to weigh in on international law—it’s three jurisdictions beyond his. Rather, New Yorkers need their mayor to deliver on security, transportation, employment, education, sanitation, and housing.
In some sense, these weaknesses seem small. Talking about stuff they don’t know. Talking about things that are beyond their responsibility set.
Is that really a big deal?
I think it is. Because they reveal a bigger problem: one of character. And it’s the development of character that bequeaths Americans good leaders.
I Could Not Afford It
Look by contrast at Abraham Lincoln.
In the midst of the Civil War, when he faced the problem the President is responsible for—keeping the country safe and united—he received distress calls coming from the West after Dakota Nation raids killed at least 300 Americans, including women and children.
General John Pope sent the list of 323 Native Americans whom he had decided should be executed to Lincoln for approval. The leaders in the West demanded mass executions: “Death to the Barbarians” read one newspaper headline.
Lincoln refused the popular demands. Instead, he wrote to Pope: “[P]lease forward as soon as possible the full and complete record of their convictions.”
Lincoln burned midnight oil, poring over the cases, meticulously reviewing each one’s details. Lincoln focused on the duty of the office of the President, in whom lay the sole authority for stopping the executions.
In the end, Lincoln rejected the executions of all except 38 attackers. His party was punished at the ballot box: Republicans fared badly. He did not regret it:
“I could not afford to hang men for votes.”
Character, Our Personal Ruler
The problem with our current political leaders, simply stated, is character.
Character is the culture of the individual, the automatic learned behaviors.
Our habits.
Habits come in two flavors:
Habits are things we have. E.g. Remembering to hold the door for someone.
Habits are also things we can change—through hard work. E.g. Steering our minds away from anger and into curiosity when we hear viewpoints we don’t like.
What we do every day happens because of our habits.
A person of good character is someone who has developed daily habits we admire. Definitions will vary from person to person, but for most Americans it includes: independent thought and action, service to others, responsibility for one’s actions, hard work.
I wrote in the beginning that my objection to Trump and Mamdani’s speeches was what they talked about—things they don’t know, things that don’t relate to their job responsibilities.
But what I think I truly reacted to and what I think matters in our leaders is how they lead themselves. Their habits determine their ability to lead others.
How does Trump lead himself? He spent his career as a marketer and entertainer. He built a business not with financial acumen or negotiation skills, but with hype and self-promotion. He built his character to be well-versed in projecting confidence and distancing himself from failure.
What happens when his fellow citizens grant him authority? He dedicates that power to what he knows best: projecting confidence and distancing himself from failure, like the 2020 elections.
How does Mamdani lead himself? Mamdani comes from the academic world filled with left-wing thinkers who believe they alone see the path to save the poor from capitalism’s cruelty. Like Karl Marx, who read about factories but never actually worked in one, Mamdani speaks for people unlike him. He built his character to be someone who believes that because he and everyone around him reads the same books and believes the same views, he needs to tell the world what is moral.
So what happens when his fellow citizens grant him authority? He dedicates that power to what he knows best: opining on political topics about faraway places for which he lacks all credibility or expertise, like Netanyahu and the Middle East.
How does Lincoln lead himself? Born to poverty and an ethos of hard work, he sought out his own education and self-improvement. He served in the army. He worked as an entrepreneur, inventor, boat builder, and ferry operator. He built his legal practice through meeting the unique needs of each client, painstaking examinations of the law, and long Circuit trips on which he learned from other lawyers and judges.
So what happens when his fellow citizens grant him authority? He dedicates that power to what he knows best: undertaking dutiful study and considered problem-solving. He learned Union military tactics and Navy technology. He taught himself the specific actions of each Dakota attacker. In all he pursued, he exercised indefatigability and open-mindedness.
America’s Shortcoming
I don’t think America has failed institutions. Nearly without exception, our institutions are consistent and resilient.
That reflects the character of the people themselves. And every American I meet of all political, social, economic, or religious backgrounds, teaches me something and demonstrates empathy for others.
I don’t think America lacks leaders of good character. The most successful CEOs that I’ve met, across energy, automobiles, finance and technology, all do the same thing: spend time side by side with employees, walk the factory floor and the office floor, hear the obstacles that employees face, are honest about those challenges, and focus on solving those problems alone.
But we have lousy character in our political leaders. Trump and Mamdani happily stand amongst masses of people, but both fail to listen with open minds to voters who think differently from them. These leaders end up moralizing on subjects on which they know little and have no authority.
We don’t need (or deserve) leaders of exceptional character—Washington, Adams, Lincoln, Roosevelt, Roosevelt, Tubman, King, Booker T. Washington, Jackie Robinson.
But leaders whose character is to pander, denigrate, deny individual human worth, and ignore the principles of economics and human psychology, are worse than we merit.
Leaders who listen to all voters, respond with realistic plans, and focus on executing those plans are the ones who will receive my vote.
How do I identify those leaders?
By whether they have trained themselves to do those things. By their characters. Their habits.
For habits rule each of us. And our elected rulers’ habits ought to be worthy of the office they aspire to hold.