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I was set to record another conversation with Edwin Eisendrath for his weekly Chicago radio show on WCPT 820 AM, but Edwin suggested we do the recording live on Substack instead of Zoom. I was thrilled to do it, because I’ve been meaning to collaborate on a Substack with Edwin since our last conversation.
This turned into one of the more clarifying discussions I’ve had in a while. Edwin brings decades of experience in politics, education, and media to illuminate these.
He is the host of “It's the democracy, stupid,” on Lincoln Square. He was also former CEO of the Chicago Sun-Times, a former Chicago alderman, a former HUD regional administrator, and a former Chicago public schools teacher. He has actually governed, actually run a newsroom, and actually sat in the rooms where the corruption that erodes public trust has happened. His brilliant perspective ran through everything we covered.
We started with Trump’s Memorial Day message insulting Democrats, and from there outlined something bigger: the gap between who America actually is and who Donald Trump is, and how that gap defines this entire moment. With the country’s 250th anniversary approaching, we went big picture, analyzing how Trump undermines America’s foundational principles.
From there, we moved through the right-wing assault on multiculturalism (Edwin accurately called it “American culture”), how the Iran war has left us weaker than it found us, and the corruption that Edwin argues functions as an extra tax on every American. We ended on optimism, the earned kind, grounded in where the numbers actually are and where this is heading.
This was an excellent conversation. You can watch it in full above and read key takeaways below. Also, this will air again on Saturday afternoon on WCPT 820 AM, so go support them if you’re able!
The Wrong Man For America’s 250th
Edwin opened with something that was still bothering him from the weekend: Trump’s Memorial Day message, which managed to insult Democrats on a day meant to honor the Americans who died serving the country, regardless of party. That set the frame for everything that followed.
The Memorial Day post was another normalized desecration of the office. Edwin made this point directly: Americans who fought and died did not check a partisan box before they did it, and Trump generalized an entire group of people, many of whom died for this country. What struck me just as much was watching Fox News read the post on air as if it were a perfectly normal thing for a president to say. The president is supposed to be the best of us, not the absolute worst, and on a totally innocuous day where he could have risen above the fray, he leaned on his worst impulses instead. Edwin’s response cut to it: Does he even have other impulses?
The 250th should have been a chance to take stock of real progress, and instead, it is a backlash. I said this is what makes it so depressing that he is the one helming it. The honest version of this anniversary would acknowledge that the founders did not abolish slavery at the founding, that we had a deeply flawed beginning, and that we have made enormous gains since. The founders created a framework to pursue freedom even though they were flawed men. Trump is marking the milestone by eroding the foundational principles that the framework was built to advance with his assault on fundamental civil rights.
Trump cannot showcase the country we actually are. Edwin made the point that, beyond being the wrong man to narrate our history, Trump is incapable of celebrating the diverse, interesting, brilliant country America has become. That is why the artists who signed up for what they understood to be a nonpartisan celebration created by Congress are now pulling out as they realize it is a Trump party rather than a national one. They are saying no, and Edwin and I agreed that is the right call.
Multiculturalism IS American Culture
This was the intellectual heart of the conversation. Edwin pushed me on the language itself, and his reframe is one I am going to keep using, because it takes away the escape hatch that the word multiculturalism accidentally hands the other side.
Edwin’s reframe from multiculturalism to American culture closes a loophole. He explained that he has stopped using the word multiculturalism, because when you call it that, the other side hears a buffet they can take three items from and leave the rest aside. That is not who we are. He reached for St. Paul, from a tradition he noted was not his own: if you get rid of the hands, what is the stomach going to do? We all have to be part of this for it to be the culture we are. I told him I was genuinely glad he framed it that way, because he is right. This is not just an attack on multiculturalism. It is an attack on American culture at its fundamental essence.
The assault on this culture is fundamentally anti-American. I walked through how they are lying about the history of America, acting as if it has always been a white Christian nation, when in reality, this country was built by slaves, and the Black community went on to shape its music, its art, its literature, and its politics. Edwin added that it runs through every aspect of our lives. To diminish that and pretend it was not the foundation of America is to attack the country itself.
The blood-and-soil rhetoric is a transnational project. I connected the dots on the ethno-nationalist language: Vance’s blood-and-soil framing, Trump talking about the British blood running through the room when King Charles visited, and the same eugenic, white-nationalist vocabulary showing up in the UK with the Reform party. This is a coordinated assault on the idea of a multicultural society, and they want the benefits of that society without the people in it. They will hold a rally about deporting immigrants and then go to a Mexican restaurant afterward.
America was multicultural from the first European footfall. Edwin made the historical point cleanly: when the rest of us got here, there were already Native Americans here. America was multicultural from the moment someone from Europe set foot on the continent. I added that whiteness itself has expanded over time, that the Irish and Italians faced discrimination before being folded in, and that this is exactly why Democrats need to make the affirmative case for an immigrant-welcoming culture, including the fact that undocumented immigrants pay $100 billion in taxes annually without receiving the benefits.
The Iran War Has Made Us Weaker
Edwin has worked in that part of the world for years, and his read on the Iran war was unsparing. We both landed in the same place: there is no version of this where America comes out ahead.
Trump is negotiating with the voices in his own head. Edwin described the whiplash perfectly, the peace, then the bombing, then the peace, then the Strait of Hormuz is open, then it is not, then he controls it, but Iran has to open it. He said that earlier in the presidency, people might have called this strategic ambiguity a genius, leaving himself room to move, but we are past that now. America looks at this and sees a man who has no idea what to do. I added that when they call it the madman theory, the problem is that without the theory, you are just left with a madman.
The deal on the table solves a problem that the war itself created. I laid out the specifics: the Strait of Hormuz was open on February 27th, the day before the attacks, and Iran did not have a nuclear weapon. The deal being floated, from what I saw in Axios, is effectively a deal to return to the table to restart talks that were already happening when Trump launched the initial strikes. Scott Jennings and some Republicans are trying to claim victory, but even if the Strait reopens, economists say the damage is long-lasting. Gulf production that shut down will take time to ramp back up, and oil prices will stay elevated.
We handed Iran a weapon stronger than a nuclear one. This is the part that should worry everyone. We are left with a more extreme Iran that has realized its leverage and now holds a deterrent more usable than a nuclear weapon: the ability to short-circuit the global economy whenever it chooses. Edwin put it starkly that there is no circumstance where the United States ends this better off than before, and no circumstance where the Iranian regime is not more entrenched. We lost whatever shot at regime change we might have had when the older Khamenei died, because killing him made him a martyr.
A simpleton with no intellectual curiosity cannot win a war he does not understand. After Edwin called Trump a simpleton, I made the point that Trump lacks the curiosity required to understand the enemy, and you cannot negotiate or wage war against a regime whose mechanics you do not grasp. He thought he could go in and pull a Venezuela. Instead, he took out Khamenei and empowered the IRGC, whose decentralized structure means that taking out a few generals just elevates others. Edwin brought it home with Oman, the most beautiful and peaceful country in the Gulf, which Trump threatened to bomb this week. Edwin said he is sick of a president whose answer to every problem, high gas prices included, is to lock someone up, bomb someone, or shoot them. With the guardrails of the first term gone and only loyalists around him, this is Trump’s id fully unleashed.
Corruption Is A Tax, And America Is Starting To See It
Edwin’s framing here was one of the sharpest of the conversation, and it carries extra weight coming from a former alderman who watched colleagues go to prison over sums that would not cover a rounding error in Trump’s grift.
Corruption is an extra tax on every American. Edwin made the argument that every overpriced no-bid contract to line a friend’s pocket, every slush fund skimmed from money handed to the Treasury, comes out of your pocket and mine. The corruption is not just disgusting on its own. It is a direct cost imposed on all of us. That reframe matters because it connects the abstract scandal to the kitchen-table squeeze people are already feeling.
The $1,700 stop sign versus the billion-dollar grift. Edwin told the story of his time as a Chicago alderman, when colleagues went to jail for taking $1,700 to approve a stop sign, and people were rightly disgusted that a politician would line his pocket at the public’s expense. He asked the question directly: this guy has taken billions for himself and his friends, so where is America’s sense of outrage? I walked through the scale of it: the attempt to extract $10 billion from the IRS, settled down to a $1.776 billion slush fund for his cronies, the billions in crypto, the sovereign wealth funds investing in World Liberty Financial, the $620 million government loan to a Trump Jr. affiliated company, Trump’s 3,600 stock trades in Q1, and the NVIDIA and defense contractor holdings he profits from while greenlighting chip sales and waging war.
The Justice Department has been turned into a personal enforcement mechanism. Edwin connected the economic pilfering to the destruction of the DOJ, which now exists to keep the boss in power, punish his enemies, and line his pocket. That, he said, is the playbook of dictatorships all over the world, and we are watching it run in our own government. We elected a man through a democratic process he does not believe in, and he told us in advance, through Project 2025, that he would use the power we gave him to make sure we could never use it against him again.
It is starting to pierce through, and that is the source of real optimism. I told Edwin I am seeing the grift finally break through, with MAGA media figures as a lagging indicator who only move once their audience already has. The optimism here is earned, not wishful. Trump’s approval has collapsed into the 20s with independents, he has erased his gains with Hispanic and Black voters, and he is historically unpopular with young people. I cited Ezra Klein’s point that Trump’s obsession with Republican primaries shows he cares more about controlling the party after he is gone than about the midterm outcome itself. Edwin closed where we began, that beating Trumpism is not the whole goal. The goal is returning to a truer vision of who we are and proving that Americans can face down threats to democracy at home as well as abroad.
Bottom Line
The throughline of this entire conversation was the gap between who America is and who Donald Trump is. He insulted the war dead on Memorial Day. He is the wrong man to helm a 250th anniversary that he does not understand. He is assaulting the American culture that is the country’s actual foundation. He waged a war that left us weaker and handed Iran new leverage. And, he has turned the government into a machine for self-enrichment and retribution. But the country is starting to see it clearly, the numbers are moving, and the way out runs through a more honest and more healing vision of what America can be together.
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