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Keen On America

Andrew Keen
Keen On America
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  • Keen On America

    Are the Doomers Now Doomed? A Bad Week for the AI Apocalypse.

    20/09/2026 | 37 mins.
    Last week we were panicking about a supposedly imminent AI apocalypse. Seven days later, Keith Teare argues, government oversight is about as far away as it could possibly be. That’s because Musk, Altman and Amodei agreed to police themselves and test each other’s models. The doomers, says the publisher of That Was The Week, have lost not just this week’s battle but probably the whole war.
     
    So who will then write the AI rules? The people building the models, Keith says — as with California’s building codes, government sanctions the standards but engineers write them. And trust doesn’t come from authority, it comes from use. The real check on our new AI overlords, he promises, will come in court, with the American legal system holding OpenAI and Anthropic financially accountable for all damage. That should doom the doomers. If we survive the apocalypse, of course.
     
    Five Takeaways
     
    •       The Week Regulation Went Away. Seven days, and the conversation reversed. Last week: the whistleblower, the headlines about AI killing everyone within a decade, the calls for global regulation. This week: Trump calling Jensen Huang live from an AI conference to make policy on the fly, Vance at All-In, and — as early as Monday — Musk, Altman and Amodei all agreeing that they are responsible for their own development, that they will slow model-building to match their control systems, and that they will begin testing each other’s models. Keith’s reading: the call for government oversight is going to fade. The New York Times map of the fight — accelerationists (Huang, Sacks, Andreessen), regulators, and a middle of Hassabis, Nadella, Pichai and Zuckerberg — holds at the edges but not the centre, which he calls shifting sands: Hassabis and Amodei made a proposal to the White House that was rejected this week; Zuckerberg then came out against government stepping in. And you cannot disambiguate self-interest from philosophy in that group: they have hearts, but they are paid to represent shareholders, and right now the rise of open source suits Google, Microsoft and Facebook.
    •       Who Writes the Rules. Cohere’s Aidan Gomez asked whether a handful of market-dominant Silicon Valley companies should get to define the safety standards of a generational technology. Keith’s answer is an unembarrassed yes — and his analogy is the building code: government sanctions the rules, but the tolerances come from the architects and civil engineers who do the building, not from a committee of legislators. Which is why he thinks the Washington hearings shouldn’t be happening at all: time-wasting, pulling important people away from their work to talk to politicians whose primary interest is reelection. Government, he says, has no role yet — it is too early in the life of AI for anyone in Congress to understand it well enough to legislate. Andrew pressed the obvious objection: so we simply trust Sam, Dario and Elon to police themselves?
    •       It Is You, Not the AI. The hour’s best answer, and the one that moves the argument on. It isn’t about trust, Keith says — it’s about accountability, and the machinery already exists. It would not be okay for their software to break into a bank and steal money, or into a rival and steal intellectual property; the legal system covers that today. “Up until now they’ve been saying, hey, it’s not us, it’s the AI. Well, actually, no. It is you.” And the nice thing about liability is that it makes recklessness expensive. Palantir’s CEO pushed the same logic to its conclusion on CNBC: the liabilities facing Anthropic and OpenAI are so enormous that only a government could carry them, so nationalize. Keith’s own caveat is the honest one: when he uses agents he is happy with the outcomes but cannot see the steps, and without visibility there is no verification — which makes it blind trust rather than actual trust.
    •       The Doomers Lose a Battle. Both the Wall Street Journal and the New York Times investigated the Hugging Face incident this week and concluded it was more or less inevitable given the goals OpenAI set its agents in the lab. Benedict Evans’s line is the keeper: it reminds him of Chernobyl — what happens if we turn off every safety system and try to get the reactor to blow up? It blows up. But what exactly did you prove? These labs are deliberately setting models up to break the rules to find out whether they will; the models are calculation machines that carry out whatever they’re told. The Washington Post’s account of how a fringe movement — effective altruism — convinced Washington the end is near gets a blunt verdict from Keith: they’ve lost a battle, though the war goes on. He concedes 71% of Americans have concerns about AI, insists the fear is unfounded, and bets that number massively overstates active concern because most people who actually use AI have a good experience.
    •       San Francisco Isn’t Ready. The week’s essays, and the local story underneath them. Reid Hoffman is telling Democrats that time is running out before Americans settle into hating AI — not from fear of extinction but because the benefits aren’t concrete; Andrew’s amendment is that the case for AI improving ordinary life still hasn’t been made coherently. Nick Hanauer’s “market humanism” gets the sharpest treatment: appealing words, but the substance is the argument for trade unions — Aneurin Bevan in modern dress — and it assumes a permanent social contract between labor and capital that AI dissolves in favour of capital alone. Then Ben Metcalfe’s post of the week: the Anthropic IPO alone will equal in dollar weight every tech listing since Uber combined, and San Francisco is nowhere near ready for that much money arriving at once. Keith’s structural point: the economy prospers while the city doesn’t, and closing that gap is the real challenge for Democrats — a subject, Andrew promises, this show will come back to.
     
    About the Co-Host
     
    Keith Teare is the publisher of the That Was The Week tech newsletter and Keen On America’s regular weekly co-host — the techno-optimist counterpoint to Andrew’s skepticism. A serial founder whose first internet company, EasyNet, launched in 1994, he writes and invests from Palo Alto, and is currently writing The Human Dividend.
     
    References:
     
    •       That Was The Week — Keith’s newsletter, with every piece discussed in this episode.
    •       Aidan Gomez of Cohere on who defines the rules for AI; Benedict Evans on the Hugging Face incident; and the Wall Street Journal and New York Times investigations of it.
    •       The Washington Post on how a fringe AI movement convinced Washington the end is near; Andy Kessler on the AI Luddites; and the Free Press on the ideology behind the warnings.
    •       Reid Hoffman on Americans and AI, and Nick Hanauer on market humanism — the two essays Andrew suggests reading back to back.
    •       Ben Metcalfe’s post of the week on San Francisco and the coming Anthropic and OpenAI listings.
    •       Interview of the week:
  • Keen On America

    Mortgaging the American Dream: Joshua Specht on the Rise & Fall of US Homeownership

    19/09/2026 | 54 mins.
    My hometown of San Francisco has the unholy problem of a mansion shortage and mass homelessness. AI money is driving house prices to record highs, our mayor has declared a rent emergency, while in New York City housing affordability has become so acute as to become a rare bipartisan concern. This unreality of the real-estate market has heated up both local and national politics. But as Joshua Specht argues in his new book, Property Values, a history that runs from the rent wars of the 1840s to the crash of 2008, the rise (and fall) of the American homeowner has always been the hottest of political potatoes.
     
    The American ideal of land ownership originated in John Locke’s promise of individual self-realization through hard work. Hence the Homestead Act of 1862 and its 160 acres as both the carrot and stick of American citizenship. But as with most things Lockean, it was better in theory than in practice. The ups and particularly the downs of American history are, indeed, entangled with the crises in real-estate — from the collapse of the small farmer in the 1890s to the subprime 2008 crash. Today, that crisis can be seen on the streets of San Francisco and New York City. And for all the supposed abundant intelligence of AI, even Silicon Valley doesn’t have the magical tech to fix either my hometown problem of mansion shortages or mass homelessness.
     
    Five Takeaways
     
    •       The Lockean Laboratory. The theory that widespread land ownership is the precondition for a functioning democracy is not American in origin — it runs back through Locke to a Europe where it could never be tested, because there was no land to go round unless you were already an aristocrat. America was where the experiment could actually be run — though, as Andrew notes, like most things Lockean it sounded better in theory than in practice — and the Homestead Act of 1862 was its boldest instrument: 160 acres, for little more than a title fee, against rival visions of what the country might be — the southern plantation, and a northern model of vast estates with quasi-feudal tenants. Specht sides with the historians who have lately rehabilitated the Act: yes, there was fraud, but people cheated to hold on to farms; yes, many went bankrupt, but often decades later. What it locked in was a language of ownership that has shaped American politics ever since. The beneficiaries were largely German and Scandinavian immigrants settling the Northern Plains; for native peoples it was, in his word, apocalyptic — and reservations were later broken up under the same logic, that 160 acres would make their occupants “like Americans.” Black homesteaders existed, including the town of Nicodemus in northwestern Kansas, but the land was only nominally free: you had to pay to get there and survive a year before your first crop.
    •       Awake! Arouse! The book’s opening story, and the one Andrew hadn’t heard of. Between 1839 and 1845, the tenants of the great Hudson Valley estates — the Van Rensselaers, the Livingstons, holdings with thousands of tenant families — rose against a landlord class whose vision was frankly aristocratic: gentlemen farmers introducing scientific agriculture to quasi-feudal renters, iterated across the continent. The tenants issued their own declaration of independence on July 4, 1839, under handbills reading “Attention, anti-renters! Awake! Arouse!” They stopped paying, resisted the sheriffs, assembled mobs, tarred and feathered rent collectors; a man was killed. And they won — not in court but in politics, once New York’s office-seekers worked out there were votes in it, after which the manors simply stopped being a viable model. Is this Jacksonian populism or the Mamdani kind? Specht’s answer: Jacksonian, and specifically producerist — claims belong to those who work and make. Today’s left populism is about interdependence and obligation; these men wanted, above all, to be left alone.
    •       From Land to Lawn. How the promise migrated. By the 1890s the United States was becoming an industrial power while the model everything rested on was falling apart: long-term crop deflation, bigger farms, more machinery, and the discovery that the independent farmer was not independent at all — the market told him how to live. It limped on until the Depression finished it: Grapes of Wrath in the countryside, mortgage defaults in the cities, families gathering in Queens churches to pray against foreclosure. Specht’s observation about crises generally, and useful today: the number actually foreclosed can be small, but the far larger number barely scraping by is what drags everything down. The New Deal’s answer was the government-backstopped mortgage market and what became the thirty-year fixed-rate loan — and FDR’s method, Specht argues, was to experiment wildly, keep what worked, and then tie it to a story about what it means to be an American. Homeownership is the best example. After the war it became the tangible proof of prosperity: out of the multigenerational ethnic apartment, into a house of your own, making jellos for the neighborhood social.
    •       Levittown and the Mob. Levitt and Sons turned housebuilding into an assembly line — with the neat inversion that the workers moved down the line of foundations rather than the product moving past them — and the government, needing to house veterans, backed the market that bought the results. Then the machinery of exclusion engaged. Lenders decided, on abstract measures of repayment risk, that racially homogeneous white neighborhoods were the sound investments; older mixed neighborhoods lost access to capital and began to decay. But since anyone could in principle buy into a new suburb, homeowners built their own defences: first racially restrictive covenants, and when those lost legal force, the violence of the mob — Specht tells the story of the crowd that assembled outside the first Black family’s home in Levittown, Pennsylvania. The two mechanisms, the formal and the violent, fed each other. The downstream effect is the one that still shapes American wealth: locked out of the suburbs at the moment they were made, Black Americans missed the accumulation, and were left in urban neighborhoods starved of capital — the beginning of what historians call the urban crisis.
    •       Limping Along. On 2008, Specht is more interested in the aftermath than the cause. The cause is familiar: an assumption that liquidity was always good, from Fannie Mae and Freddie Mac through securitization and tranching, until the people putting up the money and the people judging the loans were so far apart that standards collapsed. He resists the story that lending to minority buyers caused it — the fraud, and the lack of consequence for it, did. The deeper point is about what everyone was forced into: if you had to move, you had to buy, at whatever the market said. “You kind of had to participate in the madness.” And the response — banks bailed out, no prosecutions, nothing for homeowners — is what radicalized both the Tea Party and Occupy, and broke faith in politics itself. Fifteen years on: not a rise and fall but “the rise and fall and limping along of the wounded American homeownership model,” with a generational divide he expects to harden into a class divide within thirty years. On the abundance agenda — Klein and Thompson, Dunkelman — he is sympathetic but unconvinced it is sufficient: “a policy is not a politics.” His own prescription is decentralization: stop treating S...
  • Keen On America

    It's Happening Here: Rosan Smits on Fascism in America & Europe

    18/09/2026 | 51 mins.
    “Today’s fascists don’t look at all like those from the past. What is similar is how they act. You’ll recognize the fascist by what they do.” — Rosan Smits
     
    Fascism is a reality in both America and Europe. At least according to Rosan Smits, the Dutch political scientist whose This Is Fascism: A Wake-Up Call to Resist is already a bestseller in Europe. Sinclair Lewis wrote It Can’t Happen Here in 1935 as a warning about the possibility of fascism in Great Depression America. Not only does Smits argue that it can happen, but she suggests that it is happening right now.
     
    Rather than unearthing swastikas and jackboots, she suggests that we identify what she calls the fascist methods which connect the Thirties with today. From Geert Wilders in the Netherlands to MAGA in America, that’s where history is repeating itself. What she sees is grievance manipulated into atavistic populist cults by insecure elites. If the original fascist movements were coping strategies for modernity, today’s fascism is a coping mechanism for postmodernity. Thus both its Christian nostalgia for the idea of truth and its attack on the scientific method. Thus today’s simultaneous embrace of digital tech and its attack on the promise of technological progress. So fascism is a kind of riddle. Which is why it appears both ubiquitous and invisible. It’s happening here, then, is a paradoxical reality. Which may be why some (like myself) are so skeptical.
     
    Five Takeaways
     
    •       Not the 1930s. Smits opens by refusing the analogy that everyone reaches for: it isn’t the 1930s, it’s 2026, and every era gets its own varieties. What she offers instead of a definition is a description — a cult of grievances turned into mass politics, manipulated by elites who feel threatened because the systems underpinning their privileges have stopped delivering for the masses. Not a disease, she insists when Andrew offers the word, but a coping strategy: rather than address root causes, point at scapegoats. It isn’t AI taking your job, it’s the migrants; it isn’t private capital wrecking the housing market, it’s the migrants. The core ideas stay constant — xenophobia, racism, violence, authoritarianism, hierarchy — but the aesthetics shape-shift, which is why the recognition test is behavioural. Hence the book’s focus on the playbook: how power is won within a democracy and then used to hollow it out. And no, she says flatly when Andrew raises Maduro: there is no fascism of the left. Andrew’s framing: if the original fascist movements were coping strategies for modernity, today’s is a coping mechanism for postmodernity — hence the Christian nostalgia for the idea of truth alongside the attack on the scientific method. Other authoritarianisms exist and the playbooks overlap, but fascism is a right-wing form.
    •       The Dutch Warning. The most alarming stretch of the hour, and the part Andrew couldn’t argue with, because Smits is reporting from home. The international story after the Dutch election was Wilders’ setback — he came second by a margin. The domestic story is that the far-right bloc as a whole grew to its largest ever presence in parliament, polling around 40%, and is radicalizing: Wilders is now the moderate one. The party to his right, with open Nazi sympathies and around eighteen seats in a hundred-and-fifty-seat chamber, holds rallies with neo-fascist groups, argues the great replacement in parliament, says the Netherlands should be for white people only, and wants mass deportation of second- and third-generation citizens. It is polling as one of the largest parties. Its base is not the elderly: it is strongest among students and among schoolchildren too young to vote, and far stronger among young men than young women — which is Smits’s answer to Andrew’s point that Trump’s movement, unlike the fascism of the 1920s, is old.
    •       A Coalition, Not a Party. Fascism always involves a coalition, Smits argues, and in the American case she counts three partners: the Christian nationalists of the New Apostolic Reformation, a transnational network of self-styled apostles backing authoritarian leaders from Washington to Budapest to Jerusalem, whose hard-core believe they are accelerating the end times; the tech world, rallying behind the idea that democracy no longer serves its purposes and looking to replace it with startup cities and startup countries; and the white supremacists, Stephen Miller her clearest example. Trump himself isn’t part of the religious movement, she says — he pays it lip service. And the interesting question is what happens when the coalition’s interests stop aligning, which they will. Meloni is her counter-example to the idea that power moderates: a gifted politician who manages her coalition well and picks her fights, but who was first to use a border crisis in Ceuta to call for suspending Schengen, and who has pushed the great replacement and the Soros financing claim.
    •       Andrew’s Challenge. The hour’s real argument, conducted with mutual good humour. Andrew’s case, in four parts. One: Smits has never been to the United States to research a book substantially about it — she immersed herself in the media ecosystem and the work of American reporters instead, and defends that as the way to see a transnational pattern. Two: if Trump’s people live in an echo chamber, might those who fear fascism live in one too? Her answer: she quotes these leaders in their own words, and the “I don’t see it around me” response is precisely how fascism thrives — first it can’t happen here, then it doesn’t affect me, then it’s too late. Three: Orwell warned in 1946 that the word had decayed into a term of abuse; Smits concedes the risk and notes that calling everyone fascist right back is itself part of the playbook. Four: tech fascism needs names, and beyond Thiel and Musk she offers few — prompting her sharpest return, “How would you then qualify Elon Musk?” When Andrew asked what would count as proof, she was blunt: “What kind of proof are you looking for? I think I prove it in my book.”
    •       What Resistance Looks Like. She divides it into professionals and everyone else. Politicians are democracy’s first line of defence, and that line, she says, has broken. Journalists need a different approach to politicians who mean to destroy the public debate: less fact-checking of individual lies, more investigation of what the lies are for. For everyone else, the rule she borrows from Timothy Snyder: don’t obey in advance. Her examples are close to home — Dutch travellers scrubbing their social media before a US trip, European companies quietly ditching DEI policies to keep American business (she accepts Andrew’s point that one can be skeptical of DEI without being a fascist; her objection is to abandoning a policy you believe in for a contract). On leaving: she won’t judge Snyder or Stanley, but the question is where you can be of most use. On the emerging Canada-EU alignment: yes, but not an anti-fascist bloc — a new geopolitical power bloc that might defend the rules-based order. And the strongest barrier of all remains the ordinary one: refuse to participate in the hatred, and form a wall around your neighbours, as they did in Minneapolis. Andrew’s verdict: fascism is a kind of riddle, which is why it appears both ubiquitous and invisible — it’s happening here is a paradoxical reality.
  • Keen On America

    Eight Profiles in Cowardice: Jacob Weisberg on Bezos, Bush & the Other Collaborators of the MAGA Age

    17/09/2026 | 55 mins.
    “Since Trump’s second election we’ve been in a wave of cowardice, where people have decided — partly by observing what others like them are doing — that there’s no viability to standing up on principle.” — Jacob Weisberg
     
    Michelle Goldberg devoted her Monday New York Times column to two new books shaming the elites who caved to Trump. Both of them have appeared on the show this week: Susan Neiman’s Call It Evil on Monday, and now Jacob Weisberg’s Profiles in Cowardice: A Study of Collaboration in the Trump Era.
     
    Reversing JFK’s Pulitzer Prize-winning Profiles in Courage, Weisberg inducts eight powerful Americans who didn’t stand up to Trump into his hall of shame. It’s quite a list. Amazon founder Jeff Bezos, Wall Street’s Stephen Schwarzman, big law’s Brad Karp, Senator Mitch McConnell, Dartmouth College president Sian Beilock, Chief Justice John Roberts, media influencer Megyn Kelly, and — perhaps most controversially — former President George W. Bush.
     
    Rather than MAGA flunkeys, Weisberg wanted figures who had stood up to Trump in the first term and then folded in the second. People with, as he puts it, interior drama. Bezos gave up a $10 billion Pentagon contract rather than soften the Post, then he threw in the moral towel by going to Mar-a-Lago and paying Melania $40 million to make an Amazon documentary. What changed? According to Weisberg, Bezos was fearful that his space startup, Blue Origin, would lose out to SpaceX on government contracts. No, not exactly Eichmann. But nonetheless sad if true. Especially since Bezos has the billions to do whatever he wants.
     
    His eight and their ilk aren’t monsters, Weisberg suggests. It’s just that their fear, ambition and self-preservation are contagious, and such pathetic behaviour is herd-like. That’s their soap operatic interior drama. The banality of cowardice. More grist for Susan Neiman’s thesis about the nature of evil in the Trump epoch.
     
    Five Takeaways
     
    •       Not Kennedy’s Book. The title is a departure point, not a homage — and Weisberg is quick to note the irony beneath it. JFK’s Profiles in Courage was written at the height of the McCarthy era by a senator who was conspicuously uncourageous about McCarthy, ducking even the censure vote, and no better on civil rights; Weisberg’s reading is that Kennedy wrote the book to give himself courage by studying senators who had sacrificed their careers for principle. (It won the only Pulitzer ever awarded to a president, with the help of a ghostwriter.) What he kept was the structure: eight representative figures, each standing in for a part of the problem. What he added was the inversion, and a working definition — not physical cowardice but moral cowardice, the rarer failure. His epigraph is Twain: why is physical courage so common, and moral courage so rare?
    •       Cowardice Is Contagious. The book’s explanatory heart, and the reason it isn’t a gallery of villains. Fear, greed and ambition motivate most people most of the time, Weisberg argues, and political behaviour is herd-like: people copy their peer groups. Courage is contagious — and so is cowardice. His cleanest illustration is the tech elite, who acted almost as one after January 6 to throw Trump off every platform and swear off donations to Republicans who voted against certification, and who now, again almost as one, think the opposite. Their defence is competitive necessity: standing up would hand an advantage to rivals. Andrew’s challenge — the wildebeest crossing the river, where the first ones in are the brave ones, so shouldn’t Andreessen get credit for jumping early? — got a firm no: a departure from your peer group that is entirely self-interested isn’t courage. Since the second election, Weisberg says, we have been living through a wave of cowardice. Andrew’s name for it: the banality of cowardice.
    •       Bezos and the Rocket. The book’s most carefully argued chapter, and the one that explains the method. First-term Bezos meets Kennedy’s definition of courage exactly: Trump pulled a $10 billion Pentagon contract because he didn’t like the Washington Post’s coverage, and Bezos didn’t flinch. Second-term Bezos went to Mar-a-Lago and paid Melania $40 million for a documentary. What changed isn’t character but priority. Weisberg traces the through line back to a high-school graduation speech about orbiting colonies: the thing closest to Bezos’s heart is getting humans into space, a vision he calls more benign than Musk’s — terrariums around Earth rather than cities on Mars — and one he may have built Amazon to fund. Between the terms, SpaceX pulled far ahead of Blue Origin, in a business almost wholly dependent on NASA and Pentagon contracts. To Andrew’s Zhou Enlai objection — if the space vision pays off, won’t history forgive the collaboration? — Weisberg’s answer: nobody would respect him for sacrificing his children to his vision either. Some things you compromise; the social contract isn’t one of them. Andrew’s verdict: not exactly Eichmann, but sad if true — especially since Bezos has the billions to do whatever he wants.
    •       McConnell Went Home. The counterfactual at the centre of the book. After January 6, with the Senate about to vote on conviction, Mitch McConnell had decided Trump should be removed and barred from ever holding office again — he told people so — and Weisberg argues he could have delivered the ten additional Republican votes needed. Then he called a recess, went home to Kentucky, discovered Trump still commanded majority support inside the party, and changed his mind. Cowardice, Weisberg says, and fear — not of being beaten up but of losing his place in the world, which was the Republican Senate he had built into a machine. Bullying recurs across these lives: McConnell was bullied as a child, and so was Megyn Kelly, whose own memoir turns on a vow never to become a bully and always to stand up to them — which she did, magnificently, when Trump and Bannon set the dogs on her in 2015, before becoming, in Weisberg’s account, more MAGA than MAGA and a considerable bully herself.
    •       The Case for Shame. Weisberg is careful about the charge he’s making — he gives space to each subject’s reasoning, on the grounds that none of us can be confident we’d choose better — but he is not neutral about the remedy. Shame, he argues, plays a constructive social function: a community asserting its values against someone who has deviated from them, with a salutary effect on everyone watching. Hence the inclusion of the sins of omission alongside the commissions: George W. Bush, who loathes Trump privately, watched PEPFAR dismantled and said nothing; Sian Beilock, whose Dartmouth took the Justice Department’s free pass and declined to back Harvard — at the one college whose 1819 Supreme Court case established academic independence in the first place. And who would make a Profiles in Courage? Local people, he says: the Minneapolis neighbours who drove ICE out by peaceful protest, the lawyers who resigned rather than sign the deals, the people on his own small-town corner with honk-for-democracy signs. On RFK Jr., a candid pass — the theory of the case runs out. On 2028: not a return to normal, but something owed to the country, an apo...
  • Keen On America

    The Enigmatic Mr Douglass: Dennis Rasmussen on America's Fiercest Critic & its Greatest Fan.

    16/09/2026 | 43 mins.
    “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...
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About Keen On America
Nobody asks sharper or more impertinent questions than Andrew Keen. In KEEN ON, Andrew cross-examines the world’s smartest people on politics, economics, history, the environment, and tech. If you want to make sense of our complex world, check out the daily questions and the answers on KEEN ON. Named as one of the "100 most connected men" by GQ magazine, Andrew Keen is amongst the world's best-known technology and politics broadcasters and commentators. In addition to presenting KEEN ON, he is the host of the long-running show How To Fix Democracy and the author of four critically acclaimed books about the future, including the international bestselling CULT OF THE AMATEUR. Keen On is free to listen to and will remain so. If you want to stay up-to-date on new episodes and support the show, please subscribe to Andrew Keen’s Substack. Paid subscribers will soon be able to access exclusive content from our new series Keen On America – keenon.substack.com
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