Keen On America

“You should fight against tyranny in any form it takes. You’re not betraying the founding by standing up to tyranny — you’re following in their footsteps.” — Dennis Rasmussen
 
After Lincoln, he was the best known man in nineteenth century America. And the most photographed too, some 160 portraits of the ex-slave’s unmistakable face still surviving. So there was nothing hidden about Frederick Douglass. And yet the more we know about this most remarkable American, the more enigmatic he becomes.
 
At first, he was America’s fiercest critic. In the early 1840s he accused the founders of being “little better than a band of pirates” and described the Constitution as a “wicked compact.” By 1851, however, he radically revised his view of that same Constitution, eulogizing it as “a glorious liberty document” that outlawed slavery outright. So why did Douglass change his mind so radically? Is it really possible that he was simultaneously America’s fiercest critic and its greatest fan? That’s the riddle at the heart of Dennis Rasmussen’s new book Frederick Douglass’s American Founding.
 
Rasmussen reminds us that Douglass got his political education from William Lloyd Garrison, the unbending New Englander who burned a copy of the Constitution and ground its ashes under his intolerant heel. Then Douglass — having moved to Rochester, started his own newspaper, and fallen in with Gerrit Smith’s political abolitionists — spent two years changing his mind about the Constitution. His logic was startlingly modern. Scalia before Antonin Scalia. Studying the historic document like a biblical scholar, Douglass argued that it never mentions slavery nor race. So the rights it confers, he argued, belong to all Americans. This exegesis made him more militant than Lincoln, because he argued that such a careful reading of the Constitution demanded immediate emancipation.
 
Was Douglass bought or paid off by Gerrit Smith? Naturally the bitter Garrisonians said he was. But Dennis Rasmussen disputes this, arguing that the timing doesn’t work. What Douglass earned instead, Rasmussen argues, was the right to call himself and his fellow abolitionists the founders’ true heirs, more American than even Lincoln and the Republicans. So no mystery, then. The most familiar face in America confessing, in public, that he had been wrong for a decade. If only we had such political enigmas today.
 
Five Takeaways
 
•       Band of Pirates. Where Douglass started. Escaping slavery on Maryland’s Eastern Shore at twenty, he entered the abolitionist movement under William Lloyd Garrison — editor of The Liberator, organizer of the largest antislavery society, and the man who called the Constitution “an agreement with death and a covenant with hell,” once burning a copy at a rally and grinding its ashes under his heel. Through the 1840s Douglass held the Garrisonian line: the founders were hypocrites who complained about a three-penny tax while kidnapping and enslaving a huge share of the population; the Constitution was not merely flawed but evil, with its three-fifths clause, fugitive slave clause and slave trade clause. And these were not respectable opinions. Rasmussen’s reminder: even in the North, abolitionists were the tiniest and most despised minority in American politics — Garrison was tarred, feathered and dragged around Boston by a rope.
•       The Two Years That Changed Him. The conversion ran from roughly 1849 to 1851, and it had a geography. Douglass left the East Coast for Rochester and started a newspaper against Garrison’s wishes, landing in the heartland of the political abolitionists — the Liberty Party, the Radical Abolition Party — who believed slavery should be fought through the ballot rather than outside it. (The Garrisonians held the opposite: to vote at all was to uphold an evil system.) Having to defend his position in print, week after week, exposed him to arguments he hadn’t met. The Garrisonians cried corruption: Gerrit Smith, one of the richest men in America, funded the paper and held the antislavery-Constitution view, so Douglass had been bought. Rasmussen finds the charge both unfair and untrue — the money came after the change of mind was mostly complete — and hears in it the same condescension the Garrisonians showed when they wanted Douglass to narrate his enslavement and leave the philosophical heavy lifting to whiter figures.
•       Read the Words on the Page. How do you get from “wicked compact” to “glorious liberty document”? Douglass’s answer was a method, and it is startlingly modern. Forget the intentions of the framers; read the text. The Constitution nowhere mentions slaves or slavery. It nowhere mentions white or black, or any euphemism for racial difference. Its preamble promises to establish justice and secure the blessings of liberty. Therefore its provisions apply equally to everyone born here — and the supposedly proslavery clauses can be construed, chapter and verse, to have nothing to do with slavery at all. Rasmussen is honest about the history: as an account of what the framers meant, no, it doesn’t hold — he has written a whole book on the Philadelphia convention, where proslavery framers were plainly present. But as a reading of the words themselves, “it’s far more interesting than you might think,” and Douglass’s case is stronger than anyone expects.
•       More Radical, Not Less. The hour’s central correction, and the reason this isn’t a story about a radical mellowing with age. Douglass’s new position went beyond Lincoln’s. The respectable antislavery view of the 1850s was “freedom national” — keep slavery out of the territories, leave it alone in the South. Douglass was among a tiny handful arguing that the Constitution already forbade slavery everywhere and demanded immediate emancipation. And after the conversion he became more militant, not less: more willing to countenance violence against slaveholders and slave catchers, and more emphatic in denouncing a country now openly betraying its own founding law. He also claimed the founders’ mantle for the abolitionists rather than for Lincoln and the Republicans: the founders fought tyranny in their time; we fight it in ours; we are their true heirs. The parallel with the colonists was structural, not moral — he said repeatedly that the tyranny endured by the enslaved was a million times worse than a tax on tea.
•       Wrapped in the American Flag. The legacy, and the reason the book lands in 2026. Douglass’s reading made Black Americans constitutionally American by definition: the document recognizes only citizens and aliens, and “I was born here — so I am a citizen, wrapped in the American flag just as much as anyone else.” That argument runs straight through to King’s promissory note in “I Have a Dream,” and underneath the twentieth century’s long argument about whether to claim America or leave it. There are complications Rasmussen doesn’t hide: the Garrisonians and John C. Calhoun agreed the Constitution was proslavery, a strange meeting of minds; his greatest speech, “What to the Slave Is the Fourth of July?”, was delivered mostly to white audiences, as most of his subscribers were white; he split with Elizabeth Cady Stanton over whether the Fifteenth Amendment should wait for women; and in later life — a stalwart Republican, entangled with the Freedman’s Bank — he was, as Rasmussen puts it, all too human. And his le...

“Add up all of their wealth — it’s more than ten times the Forbes 400 combined.” — Eric Zwick
 
Yesterday, the democratic socialist Susan Neiman blamed free market economics for all the evils of our age. But the market gives and the market takes. And in America it has minted three million millionaires whose collective wealth radically outstrips Silicon Valley’s billionaires. This human backbone of American capitalism is described in Eric Zwick’s and Owen Zidar’s The Everywhere Millionaire, a book about who is really rich in America and how they got there.
 
Forget Musk and Bezos, Zwick says. The real money is a hot dog man from suburban Chicago with a superyacht called Top Dog. Three million Americans own private businesses worth $5 million or more — dentists, beer distributors, HVAC contractors, Wendy’s franchisees — averaging $25 million each. Their combined wealth, Zwick says, is more than ten times the Forbes 400. And they are everywhere in America, from Walker County, Alabama to the Lake of the Ozarks.
 
Are these millionaires evil? They are certainly obsessed, relentless, bad at hobbies and mostly Republican. But evil? Only perhaps to ideologues resentful of other people’s success. In The Everywhere Millionaire, Zwick and Zidar show — in spite of growing inequality and shrinking opportunity — that the American Dream is still alive. Democrats might take note. Especially if they want to win back power in an America still dependent on Main Street for its prosperity.
 
Five Takeaways
 
•       Three Million of Them. The book’s central fact, and it reorders the American wealth debate: the everywhere millionaires are private business owners with a net worth of at least $5 million, averaging around $25 million, and Zwick and Zidar count roughly three million of them. Add their wealth together and it comes to more than ten times the Forbes 400 combined — not ten times Musk, ten times all four hundred. The market gives and the market takes, as Andrew put it — and here it has minted a class whose collective wealth radically outstrips Silicon Valley’s billionaires. They are also, unlike the coastal fortunes, geographically everywhere: the map lights up rather than clustering in four cities, with the highest average in Walker County, Alabama, and pockets around the Lake of the Ozarks, Aspen and less famous mountain towns. Why haven’t we heard of them? They don’t sell clicks. They run unglamorous businesses — a beer distributor, a dentist with a regional network, an HVAC contractor with trucks around town — and they aren’t buying media companies to be noticed.
•       Top Dog. The characters are the book’s pleasure. Dick Portillo started a hot dog stand in suburban Chicago fifty years ago with $1,100, the son of immigrants raised in a housing project; he sold the business decades later and now owns, as Andrew put it, a different kind of housing project in Naples, Florida — the authors found him via yacht registration data, because his superyacht is called Top Dog. Was he moral? Ask Mike Ditka, whose competing Ditka Dogs Portillo set about crushing. “Probably not super moral,” Zwick conceded — which is rather the point: these are not heroes or villains, just people obsessed with growing a business. Larry Miller went from auto parts distributor to dealer to owner of the Utah Jazz (and is pictured giving Karl Malone advice on the pick-and-roll). Junior Bridgeman left the Milwaukee Bucks for the deeply unglamorous business of Wendy’s franchises and made hundreds of millions. Tracy Britt Cool left Berkshire Hathaway to build her own.
•       The Accident of 1986. Zwick thinks of the tax code as a house that depreciates and needs repairs. The Tax Reform Act of 1986 — Reagan in the White House, Bill Bradley in the Senate, both of whom had actually paid the old 70% rates as a movie star and a basketball player — was a repair job: kill the loopholes, drop personal rates below 30%. The unintended consequence was enormous. For the first time it made sense to organize a business so that its profits were taxed at the personal rate, and the pass-through revolution followed: S-corporations and partnerships surging, the more profit you made the more you kept. Every subsequent reform sweetened the deal — the Bush cuts, the 2017 Tax Cuts and Jobs Act, made permanent in 2025’s One Big Beautiful Bill. Success or failure? Zwick finds elements of both, but won’t call it an unmitigated success: this class’s tax benefits are a real part of today’s fiscal problem. One unambiguous gain — pass-throughs linked owners to businesses in the data, which is precisely how this book became possible.
•       Bad at Hobbies. What are they actually like? The typical everywhere millionaire is a white man in his late fifties or early sixties, married, with a college degree — though roughly a third of star entrepreneurs in the data are women, across eight million founders over twenty years. From fifty to seventy-five detailed interviews, the unifying theme isn’t brains: test scores turn out to be a weak predictor. It’s ordeal — sleeping on the work table in the back of the shop, years of not knowing whether it would work, a relentlessness that beats IQ. They credit luck too, and macro trends they caught early. And the tax code? “Not the first thing or even the fourth thing” driving them; raise their taxes a little and they wouldn’t notice, though they do decamp to Nevada or Florida when they retire. They’re obsessed with the business at the expense of hobbies and, sometimes, family — which makes divorce, in Zwick’s dry formulation, a naturally occurring wealth tax. Not a guarantee of happiness. Also: if your parents are in the top 1%, you are six times likelier to found a star business than someone from the ninetieth percentile.
•       The Power They Don’t Advertise. The half of the book that complicates the good news. Survey data from PPP loan recipients shows this class skews Republican and cares about regulation and taxes rather than the social issues that dominate the feed — but Zwick was struck by how many Democrats there are among them, which explains why certain policies stay off the table even when Democrats hold power. Because they are dispersed, there are everywhere millionaires in every congressional district; they don’t run for office, they fund the people who do, and their influence shows up most sharply in local and state policy — including, sometimes, restricting entry and raising prices in exactly the markets where affordability bites. Trump, for the record, is not one of them: his wealth came through media and then political power, and he was born into the top 0.1%. Zwick’s advice for Democrats chasing this class, on the day after Jentleson’s big-tent argument: stop knee-jerk vilifying people who build businesses, and pay attention to problems as they are rather than as they appear in the Twitter feed. His advice for everyone else: walk down Main Street and ask who owns what. “Is a tax on 50 billionaires gonna move the needle at all? Not really.” Andrew’s verdict: evil only perhaps to ideologues resentful of other people’s success — and proof that, despite growing inequality and shrinking opportunity, the American Dream is still alive.
 
About the Guest

“If we leave words like evil in the hands of people who are fanatical, who are demonizing, we are leaving the most powerful weapons we have in the hands of people who don’t know how to use them.” — Susan Neiman
 
Susan Neiman is cornering the market in books about evil. First there was her 2002 Evil in Modern Thought, an alternative history of philosophy. Then Learning from the Germans, her 2019 treatise about race and the memory of evil. And now Call It Evil, an attempt to understand the Trump era which offers an alternative history of contemporary economics.
 
So what, exactly, is “evil”? Rather than defining what she describes as our most “explosive” word, she gracefully dances around it with all the elliptical subtlety of a clever philosopher. In spite of its Trumpian subtitle (“Understanding the Trump Era”), the book isn’t an inventory of Trump’s crimes. Instead, it investigates why half of America accepted a man whose (evil?) character was already blatantly self-evident.
 
Her answer focuses on economics rather than politics. The major source of evil in our age, she argues, is an ideology built on a falsified Adam Smith — self-interest as the whole of human nature — propped up by evolutionary psychologists misreading Darwin, and sold so effectively that we now mistake it for common sense. In a word: neo-liberalism. The (a)moral universe of the Heritage Foundation, Milton Friedman and Margaret “there is no alternative” Thatcher.
 
So is capitalism evil? Yes, the philosopher suggests, quoting Einstein and borrowing from contemporary economists like Amartya Sen. But rather than a return to Marx, she wants us to reimagine the 19th century Kantian socialist, Eduard Bernstein, in the context of the injustices of contemporary capitalism. Rather than evil, Neiman really is a philosopher of the good. She wants us to imagine that gap between the way the world is and the way it ought to be. Doing good means standing up to evil, she says. Like Henry Fonda’s performance as the morally defiant juror in the 1957 movie Twelve Angry Men.
 
Five Takeaways
 
•       Why She Won’t Define It. Evil is “the most explosive word we have,” and Neiman refuses to reduce it to a sentence — as, she notes, Kant refused before her. It is not a theological concept (the Bible itself shows moral concepts precede theological ones); it is the point at which the gap between the world as it is and as it ought to be becomes so large “that we don’t know how to live in a world where that abyss opens up.” Children spot the gap first, though they call it unfair: the bully in the sandbox is the first lesson in a world that contains injustice. Her real argument is strategic. We have become afraid of moral concepts because we cannot give necessary and sufficient conditions for them — and the cost of that squeamishness is that the word passes to the polemical and the demonizing. Andrew pressed her twice on the dodge; her answer, eventually, was sharp: she is not unwilling to use the word, she is simply more interested in analyzing it than defining it — which is why she has called both the 9/11 attacks and the Bush administration’s response evil, two entirely different kinds, and why any single definition covering both would let one of them off.
•       The Falsified Adam Smith. The book’s core, and its surprise: a moral philosopher writing about economics. The major source of evil in our time, Neiman argues, is the ideology derived from a bad and simplistic reading of Adam Smith — that we are driven by self-interest and nothing else matters — a reading she calls not a simplification but a falsification, touted by Milton Friedman and still pumped out daily by the Heritage Foundation and the Hoover Institution. Reinforcing it: evolutionary psychologists misreading Darwin, explaining that altruism is a puzzle and that we know how hunter-gatherers thought two hundred thousand years ago (we know almost nothing). Is capitalism evil, Andrew asked — the question she never quite answers in print. “Oh, I do, actually,” she said, and reached for Einstein, a committed socialist who said so all his life. Her favorite Thatcher line isn’t “there is no alternative” but the quieter one: economics is the method, the object is to change the soul. That, she says, is exactly what has happened — and when someone tells you at dinner that human nature is just that way, they are making a philosophical claim without knowing it.
•       Not a Book About Trump. Andrew put it to her that Call It Evil is barely about Trump, and got a flat correction when he pushed further: “I really think you’re twisting my arguments.” No, she does not say we are all evil. The point of the book is not to count his sins — for that, read Haberman and Swan, “a sickening” but excellent reminder of flooding the zone — but to ask how even half the country accepted him a second time, knowing everything. Trump is the reductio ad absurdum of the ideology: unabashed, unashamed self-advantage in the most powerful job on earth, “a way of giving permission” for everyone else to behave the same way. Against that: the woman helping a stranger with a baby carriage on the subway stairs, and Alex Pretti in Minneapolis, who died protecting a neighbor’s rights. We know not everyone is evil because we all have such moments. And the 9/11 quotation Andrew found most revealing of all — Trump noting that his building was now the tallest in New York.
•       Socialism Needs More Kant. The alternative tradition, and the hour’s intellectual heart. Neiman is a Kantian — the human condition as the struggle between the world as it is and as it ought to be, with an innate sense of justice we are born capable of but not guaranteed. Against Kant she sets Hume (custom, habit, emotion: fine for ordinary life, useless when a society is built on slavery or colonialism and someone wants to challenge it) and, behind him, the Nietzscheans. Her hero is Eduard Bernstein, the German social democrat who said socialism needs more Kant, an early champion of women’s and gay rights, in London during Wilde’s trial, who voted against the First World War. What Bernstein saw in Marx is what she rejects: that ideas are superstructure, “the foam on the beer,” while economics is the drink underneath. Her contemporary proof is Zohran Mamdani, whose win everyone credited to affordability — halal sandwiches, daycare — but who always framed it as justice: it is unjust that the teachers, nurses, taxi drivers and sanitation workers who keep New York running cannot afford to live in it. And Rawls, her teacher, was moving toward a Kantian democratic socialism before the strokes.
•       How Ordinary People Behave. On Gaza she is unequivocal — yes, genocide, following Omer Bartov’s careful reversal and the Israeli human rights organizations, though she notes the gap between genocide and crime against humanity is not gigantic. What drives the global outrage, in her reading, is not antisemitism (millions of Jews are outraged too) but the use of the twentieth century’s one moral consensus — that the Holocaust was evil — to justify another crime: “the use of one evil to justify another is something that’s morally obscene.” Truman’s bomb: evil, and not only for the dead but as the opening salvo of a Cold War we are still paying for. On Arendt: the banality thesis is right — we are endangered less by sadists than by the thoughtle...

Something unprecedented happened yesterday. Sam Altman, Elon Musk, and Dario Amodei — rivals who rarely agree on anything — all called for an AI slowdown. It came after more and more doomsday warnings from experts which seem to have finally woken Congress up to AI’s potentially existential threat. Axios even claimed that Speaker Mike Johnson is considering canceling the House recess to force members back to the Capitol to discuss the crisis. This seems to have been the week that the AI zeitgeist has finally shifted. Seven days that have changed the AI world.
 
For That Was The Week publisher Keith Teare, it’s time to shut up or shut down. While he remains a sceptic about the autonomy of AI agents, he recognizes its potential danger. “The minute there is recursive self-learning, there’s no speedometer. It’s either on or off,” he says. “You either control it or you don’t.” In terms of AI policy, he argues, you can’t be half-pregnant. Either leave it alone or flip the off switch. Anything else fudges the issue and allows slippery characters like Sam Altman and Dario Amodei to pursue their own agenda.
 
I don’t disagree. The real world, however, is forever half-pregnant. Investment in AI and the upcoming Anthropic IPO are the driving force of the economy. So AI’s existential threat isn’t just to “humanity.” It’s also to American prosperity, a politically existential threat (thus Trump’s opposition to any regulation). So, yes, this was the week that the AI zeitgeist shifted. The die is, indeed, cast. But it’s only the beginning rather than the end of this remarkable story. Pass the popcorn. Predicting the future might be a fool’s game, but it’s certainly going to get real interesting.
 
Five Takeaways
 
•       Calling BS on the Slowdown. The week’s convergence was genuinely new — a Dario Amodei essay warning that humans could lose control, Altman and Musk jumping aboard, all three major papers leading with it, Congress “waking up,” and an Axios scoop that Speaker Mike Johnson is being urged to cancel the House recess. Keith’s diagnosis is withering: it illustrates “the weakness of AI leadership,” swayed by a six-week employee who resigned, wrote an essay, and went on TV. His deeper claim: there is no such thing as AI as an independent actor, so the entire scare is misconstrued — “AI is not dangerous, period.” What the slowdown talk really represents, he argues, is the economic self-interest of incumbents in containing open-source AI — rules that prevent others from playing. Is anything new, Andrew pressed? “The heat is ramped up a notch. That’s about it.”
•       No Speedometer. The episode’s logical core. If you believe recursive self-improvement can’t be controlled by humans, and that the agents it produces will be malicious, then slowing down is incoherent — “the only logical thing is not to slow it down, but to shut it down”: no Anthropic, no IPO, a ban. “The minute there is recursive self-learning, there’s no speedometer. It’s either on or off.” Scott Bessent’s speech — the week’s most prescient, in Keith’s view — made the practical version: recursion can’t be stopped, and 3,500 mostly open-source models already sit in the Hugging Face store. Stephen Witt’s NYT taxonomy (shut it down, air-crash investigations, monitoring, the kill switch — with his closing COVID-epidemiologist analogy) gets respect but fails Keith’s test: none of it solves the problem if the problem is real. In AI policy, as Andrew’s intro has it, you can’t be half-pregnant: either leave it alone or flip the off switch — anything else fudges the issue. His counter-gameplay: for AI to threaten humanity it needs biological or nuclear weapons, and that chain of events is “fantastical.” Andrew’s retort — so was hijacking planes into the World Trade Center. Keith: “9/11 is one airplane.”
•       The IPO Game. Why would the leaders sound alarms about their own products? Keith’s fork: they’re naive (buying space by taking heat out of the conversation — which won’t work, since demands to stop will only grow) or manipulative. The tell arrived mid-week: Altman told Fortune that OpenAI won’t IPO this year, given the safety discussion — which Keith reads as calling Dario’s bluff. Will Anthropic pull its $2 trillion listing? “I don’t think he is. I think he’s playing a game… a high-stakes game.” Andrew’s materialist reading: with the American economy increasingly dependent on the AI sector and its impending IPOs, nothing gets shut down short of an AI 9/11 or COVID event — the story is now about the whole future of the American economy. Keith’s post-midterm forecast: the White House does nothing, and unless Democrats take both houses, “nothing changes” — markets settle, IPOs happen, AI continues. And his path to peace: most innovations become acceptable only after they deliver the bacon; people must feel AI’s benefits to discount its fears. Andrew’s verdict: the AI zeitgeist has shifted and the die is, indeed, cast — but this is the beginning rather than the end of the story. Pass the popcorn.
•       Open Source Wins — China Included. Against Noah Smith’s America-is-winning scorecard, Keith reframes the race entirely: the real contest is open versus closed source — with the Chinese, ironically, in the open camp and the Americans building walled gardens. History’s lesson: “open source leaks like water into every crevice” — the cloud is almost 100% Linux. The week’s stranger revelation: reports that Kimi was routing every query to Claude — “there was actually no Kimi” — plus the training-dependency chain that keeps Chinese models about a year behind. The money agrees with American dominance either way: the FT’s moonshot-capitalism piece has US deep-tech VC at $246 billion (80% of it California) against China’s $105 billion and the UK’s 26 — with the power law concentrating it all into a handful of companies, and Andreessen Horowitz reporting that post-SpaceX-IPO venture returns now dwarf private equity. As for regulation: California’s new chatbot and teen-social-media laws are, per Keith, light and barely policed.
•       The Rest of the Week. Starbucks’ billion-dollar bet on the coffeehouse as antidote to lonely digital lives — Keith’s analyst verdict: Barnes & Noble tried the sofas, and “the biggest problem is the coffee isn’t very good.” How writers actually use AI, via Every’s interviews: Kevin Roose structured The AGI Chronicles himself, then let AI do what he calls three to four years of work in one — exactly, Keith notes, the process behind his own The Human Dividend. The Edmans crossover, from Monday’s interview of the week: do smart people make dumb investments? Keith’s Wall Street history says the best investors are “working class street smart kids” who smell deals — inventors are not gamblers — though Musk is the exception, and as for Dario: “I think Dario would be good at anything,” Andrew offered. “He’s pretty good at politics.” Apple’s iPhone Duo foldable arrives with, per Ben Thompson, still no AI strategy — while Facebook ships Muse, a full agent with a virtual machine that would need 27 million physical computers at Meta scale. And farewell to Bill Draper — among the first venture capitalists, first into Skype before his son Tim, a seeker of contrarian difference “a bit like AI now.”
 
About the Co-Host
 
Keith Teare is the publisher of the That Was The...

“One believes in democracy and the rule of law, and right now, the other doesn’t.” — Adam Jentleson
 
Yesterday, William Hitchcock explained FDR’s ability to build and maintain supermajorities. Today, Adam Jentleson — Harry Reid’s former deputy chief of staff and chief of staff to John Fetterman — talks about how the Democrats can build lasting power in the 21st century. The strategy is laid out in Supermajority, Jentleson’s follow-up to the acclaimed Kill Switch.
 
Is the Democratic Party too woke? “We are still too rigid” is Jentleson’s euphemistic take on the dramatic class flip in American politics. JFK won two-thirds of working-class voters in 1960, Jentleson reminds us, while Kamala Harris lost two-thirds in 2024. His prescription is FDR-style heterodoxy. Dems need to hold to their core commitments (healthcare, the safety net, progressive taxation, civil rights) while broadening their base in red states. His examples of tent wideners include a Kansan megachurch pastor, a pro-drilling Alaskan candidate, and an Iowan hopeful whose flat “no” on trans sports silenced a right-wing radio host. The model for winning back the working class, Jentleson argues, is Bernie Sanders circa 2016, an economic populist, but to Hillary Clinton’s right on immigration and guns.
 
The much maligned John Fetterman, Jentleson’s old boss, is the cautionary tale. It’s what happens, Jentleson warns, when the fighting “becomes the entire point” and a politician comes unmoored from principle. Jon Ossoff, Jentleson suggests, seems the anti-Fetterman in writing his own speeches and appearing authentic rather than opportunistic. Ossoff certainly isn’t FDR, but he might be the best chance the Dems have of defeating an increasingly authoritarian Republican party in 2028.
 
Five Takeaways
 
•       The FDR Lessons Nobody Tells. Picking up where yesterday’s Hitchcock episode left off: FDR built the New Deal supermajority not by bowling opponents over with progressive rhetoric but through a deeply heterodox coalition — including factions today’s Democrats would expel — and sold it in conservative wrappers: Social Security pitched as fiscally responsible and earned, not given (he railed against the dole in cabinet meetings). The uncomfortable ledger: FDR actively worked against every civil rights bill of his era to keep self-declared white supremacists in the tent — which means, Jentleson argues, that today’s trade-offs (a Kansas candidate with questions about trans sports, a border-security Democrat) “pale in comparison” to the compromises that built the twentieth century’s Democratic dominance. The Kansas case in point: megachurch pastor Adam Hamilton, running in a state Trump won by twenty points, holds the line on healthcare, the safety net, and progressive taxes — and the alternative to his heterodoxy is a MAGA senator.
•       Too Rigid, Not Too Woke. Asked the New Yorker’s question — is the party still too woke? — Jentleson answers with his own euphemistic diagnosis: “we are still too rigid.” The evidence is the class flip: JFK won about two-thirds of working-class voters; Harris lost about two-thirds, while the college-educated — once the party of Romney, Rockefeller, and Eisenhower — became the Democratic base. And the sociology cuts deep: education correlates with ideological rigidity, while working-class voters hold heterodox mixes — the focus-group regular who wants the 2008 CEOs jailed and undocumented immigrants deported in the same breath. Hence the echo-chamber problem (Andrew’s San Francisco testimony included): the decline of unions, parties, and Elks halls narrowed the aperture to funders and interest groups, and the Harris circle heard only itself. The fix costs nothing: choose diverse advisers, model good-faith disagreement — a preview of next week’s Susan Neiman conversation — and collect what Jentleson calls the electoral windfall waiting for whichever party does it first.
•       It’s Working Right Now. To Andrew’s two-state-solution objection — lovely in theory, impossible in practice — Jentleson answers from the November polls: Mary Peltola leading in Alaska (Trump +double digits) as a pro-drilling Democrat; James Talarico leading in Texas as a fossil-fuels-as-bridge Democrat; and Rob Sand in Iowa, whose flat “no” on a right-wing radio show — the host admitted he’d prepared follow-ups for the expected wriggle — took the wedge off the table and freed his anti-corruption message. As recently as 2009, he reminds us, Democrats held Senate seats in Arkansas, both Dakotas, Louisiana, and Montana. The forgotten exemplar: Bernie Sanders 2016 — economically populist but a 2007 immigration-bill no vote, “open borders is a Koch brothers proposal,” Lou Dobbs appearances, and gun rights to Hillary’s right — the heterodox mix that produced his crossover appeal, against Clinton’s across-the-board orthodoxy. Jentleson’s 2028 read: the primary won’t resolve for the left, and Ossoff, Cooper, and Peltola are the model — though he tips his hat to the DSA’s weeknight commitment to Robert’s Rules.
•       The Fetterman Cautionary Tale. The hour’s most personal stretch: Jentleson was John Fetterman’s chief of staff, and his verdict on his old boss — who cameoed at Trump’s convention this week — is that Fetterman shows what happens when the heterodox strategy is “taken too far”: the fighting “has become the entire point of his career,” unmoored from the principles that make divergence meaningful. On the Wall Street Journal’s reporting — the children’s hospital he refused to meet, the York police funerals he skipped — Jentleson wasn’t a source (“if you’re going to say something, you should say it on the record and put your name on it”) but confirms it “resonated with my experience.” His primary emotion: “sadness and regret… he’s letting a tremendous number of people down, including the people of Pennsylvania, who are basically down a senator.” The lesson for the book’s own thesis: heterodoxy is a powerful tool, and like all powerful tools it needs to stay rooted in why you entered politics at all — or it leads “to some dark places.”
•       The Vision Thing. Why supermajority and not Madisonian faction? Because, Jentleson argues, this era has something genuinely new: “the first time in American history where we have one political party that is entirely aligned with a sympathy towards authoritarianism” — not flashes like McCarthy or Father Coughlin (yesterday’s villain, returning), but a party whose convention this week featured Trump leading “a pledge to cheat in elections,” with no internal pushback. (FDR’s court-packing, by contrast, was the exception proving the rule: the system brushed him back in 1938.) Hence the pull quote — and yet democracy-talk alone doesn’t win: “Biden tried to run on soul of the nation… and it didn’t work.” The closing agreement, via Andrew’s wrapper argument: the New Deal and the Great Society were named visions; Clinton and Obama never articulated one. Jentleson’s candidate: finish FDR’s cradle-to-grave social insurance — wage insurance against AI’s disruptions, everything earned rather than handed out, aimed at bank accounts and the pump rather than the soul of the nation. And his 2028 intrigue, on the record: Jon Ossoff — the anti-Fetterman — who writes his own speeches, wins Georgia repeatedly, and conditioned aid to Israel early enou...