The sequence runs:
October 31, 2024: “How quickly would Trump wash his hands of Ukraine?” Pre-election assessment of Trump’s Ukraine policy as the likely winner.
March 13, 2025: “What’s in a rename?” First principled critique of Trump on the Gulf of America rename.
April 7, 2025: “How DEI destroyed itself.”
April 30, 2025: “The real battle for Europe.”
June 2, 2025: “Why everyone is talking about Bill Belichick.”
July 14, 2025: “In the age of AI, humans must keep learning.”
September 8, 2025: “Liberalism is a lost cause.”
October 6, 2025: “The bully doctrine.”
November 5, 2025: “Is Donald Trump a game theorist?”
December 2, 2025: “Eclipse of the Boomers.”
December 17, 2025: European leaders on Ukraine.
January 9, 2026: IHRA and free speech.
February 6, 2026: The Reiner case and character.
February 24, 2026: The Nixon essay.
March 18, 2026: The Trumpism obituary.
April 17, 2026: The Easter column.
The October 2024 Ukraine piece shows Caldwell in the final days of the 2024 campaign writing from a position of cool analytical distance on both American presidential candidates. The essay is neither a Trump endorsement nor a Harris endorsement. It is a prediction about how the war will change regardless of who wins. The prediction is that domestic pressure to scale back U.S. involvement will be “irresistible” for either candidate.
The essay’s sympathies are clearly anti-Biden and anti-neoconservative, but the criticism of Trump is also present. “Trump’s campaign message, muddled though it is, bodes ill for the Ukrainian war effort” is not a friendly sentence about Trump. The characterization of Trump’s “24 hours” claim as a boast and the description of the previous Trump administration as “admirably disinclined to internationalist hubris” but also as having benefited from circumstances Trump “falsely boasts” about producing, these are measured and skeptical. Caldwell is willing to credit Trump for the right policy instincts on Ukraine while refusing to credit Trump’s own account of why peace obtained during his first term.
Several observations follow.
First, the October 2024 piece establishes Caldwell’s foreign policy position before Trump’s second term began. He is anti-Biden, anti-Obama-era-neoconservative-resurgence, pro-restraint, anti-escalation, skeptical of Ukrainian government propaganda, skeptical of Zelensky, and aware that the Biden administration had been running, in his phrase, on “a junta of special interests” in the president’s “cognitive absence.” The position is a national-conservative anti-war one, but it is held with genuine analytical commitment rather than coalition necessity. Caldwell has been writing in this register on Russia and Ukraine since at least 2022, and the position does not depend on Trump being in office.
This matters for the later arc. When Caldwell writes the December 22, 2025 Europe piece attacking European leaders for goading Ukraine to continue fighting and crediting Trump for urging negotiation, he is not suddenly adopting a pro-Trump position on Ukraine. He has held the Ukraine position for years. Trump happens to align with it. When the Iran war in March 2026 violates Caldwell’s anti-war commitments, the violation is measured against a principle that predates Trump’s second term. The Ukraine position and the Iran position are continuous in Caldwell’s thinking. Trump’s alignment with one and violation of the other is how the coalition pressure gets generated.
Second, the October 2024 piece includes a paragraph that deserves particular attention. “History will liken Biden’s foreign policy to that of George W. Bush, another strange interlude when a mood of world-shaping ideological fanaticism briefly overtook the traditionally pragmatic Anglophone powers.” This sentence does a lot of work. It equates Biden’s Ukraine policy with the Bush-era Iraq War project. It names both as departures from what Caldwell considers the normal Anglophone foreign policy tradition of pragmatism. It positions Caldwell’s own preferred foreign policy as the restoration of that tradition, available under Obama’s withholding of arms from Ukraine, available under Trump’s first-term disinclination to intervention. The position is older than Trump and will outlast him. Caldwell’s foreign policy commitments are not coalition-bound. They are temperamental and historical.
Third, the October 2024 piece shows that Caldwell was already making the kind of institutional-failure critique of Biden that he will later apply to Trump. The line “Biden administration has been run, in the President’s cognitive absence, by a junta of special interests” describes the same kind of governance failure that Caldwell will later describe around Trump’s shrinking advisor circle in the April 2026 Easter column. In both cases, the diagnosis is that a president’s personal failings have allowed his administration to be captured by a narrow set of insiders who produce decisions at odds with the country’s interests. The diagnosis is applied to Biden in October 2024 and to Trump in April 2026. The analytical framework is consistent. The target shifts as events warrant.
This shows something important about what Caldwell is doing across the entire arc. He has a relatively stable set of analytical commitments, rooted in national-conservative Catholic pragmatic-realist political thinking. The commitments include skepticism of ideological fanaticism in foreign policy, preference for democratic consent over expert rule, concern for institutional decay under both Democratic and Republican administrations, and critique of governing by captured-advisor networks. These commitments produce criticism of Biden in October 2024 and criticism of Trump in April 2026. The criticism of each is framed in the same terms because the commitments are the same.
Fourth, the October 2024 piece refuses the endorsement move. Caldwell does not say Trump will be better than Harris on Ukraine. He says both will find domestic pressure to scale back irresistible. The asymmetry is that Trump’s campaign rhetoric promises faster withdrawal while Harris’s silence suggests she will manage the wind-down more quietly. Neither approach is endorsed. Both are predicted. This is the Caldwell of the Financial Times era: a writer who produces predictive analysis rather than advocacy. The analysis turns out to be largely correct. Both candidates, had Harris won, would have faced the same pressure, and the Trump administration has indeed pushed Ukraine toward negotiation as Caldwell predicted.
Caldwell held a consistent set of commitments from before the 2024 election, applied them to both candidates without coalition bias, wrote pre-election analysis that refused endorsement while predicting outcomes, criticized Trump’s Gulf of America rename in his first month in office, endorsed Trump’s DEI assault three weeks later, continued to work across a wide range of subjects for most of 2025, and began in January 2026 to produce increasingly serious criticism of Trump administration actions that violated his foreign policy and civil-liberties principles.
Caldwell is a national-conservative Catholic pragmatic-realist writer whose commitments predate and will outlast the Trump presidency. He supported Trump’s second-term policies on civil-rights bureaucracy, immigration, foreign policy restraint on Ukraine, and the restructuring of the Democratic-aligned State Department. He criticized Trump’s methods on linguistic coercion from the first month of the second term, criticized Trump’s IHRA move once it became serious, criticized Trump’s character after the Reiner mockery, overreached in the Iran war obituary, and settled into a sustainable Catholic position in the Easter column.
The writer across the sixteen pieces is recognizably the same man. The method is stable. The commitments are stable. The targets of criticism and endorsement shift with events. What the extended arc shows is not a writer moving from enthusiasm to disillusionment but a writer applying his long-held principles to a rapidly changing political situation and producing the mix of endorsement and critique that those principles require.
The October 2024 piece uses the pre-election moment to establish a framework that will guide Caldwell’s writing throughout the Trump administration. The framework is that American foreign policy is now captured by domestic partisan structures, that both major parties face constraints from their bases, that the next administration regardless of party will have to manage domestic pressure for restraint, and that the foreign-policy establishment’s preferred activism will continue to lose legitimacy. The framework is applied to the Biden administration in October 2024. It is applied to the Trump administration throughout 2025 and into 2026. The consistency of application is what makes Caldwell’s writing trustworthy to readers across coalition lines. He does not change his framework based on who is in power. He applies the same framework regardless, and lets the criticism fall where it lands.
A reader knowing only the October 2024 piece would have predicted the shape of the subsequent arc with reasonable accuracy. Caldwell would be generally supportive of Trump on Ukraine and European policy, generally supportive of Trump on domestic anti-administrative-state work, and generally critical of Trump on methods that violated his principles of free expression and democratic legitimacy. This is what the subsequent arc delivers. The arc is not a story of changing loyalties. It is a story of consistent principles applied to an increasingly consequential sequence of events.
The coalition-crisis register of the January-April 2026 pieces is not an aberration. It is one phase of a longer application of stable principles to events that required increasingly direct criticism. The writer at the end of the arc is the writer at the beginning, applying the same tools under progressively more demanding conditions. What looks from inside the crisis like a dramatic shift looks from the full sequence like continuous application of stable analytical commitments.
March 13, 2025: “What’s in a rename?”
Caldwell writes:
Defeating woke with principles turns out to be hard. Trump tried this approach in his first term. Now he is operating on a cruder basis: that of rewarding his friends and punishing his enemies. He has scored some successes. But he is in danger of forgetting who his friends are. The many voters who backed Trump because they actually do care about freedom of speech are unlikely to resign themselves to pretending the Gulf of Mexico is called something else.
This closing paragraph is prophetic. Written in March 2025, it predicts the entire arc of the subsequent thirteen months. Trump will continue to operate on the cruder basis, will continue to score policy successes, and will continue to forget who his friends are. The friends Caldwell is thinking about in March 2025, “voters who backed Trump because they actually do care about freedom of speech,” are the same constituency whose interests will be violated by the IHRA policy in January 2026. The category of principled Trump supporter who can be alienated by Trump’s coercive linguistic politics is already a concern in March 2025. The structural critique is in place before any of the later crises.
Caldwell was willing to endorse Trump policies he supported and criticize Trump methods he could not defend on his own principles. The coalition position was always conditional. The conditions were always legible. A pro-Trump reader in 2025 who thought Caldwell was a reliable ally was reading carelessly. A reader who took Caldwell’s March 2025 Gulf of America critique seriously would have known that the same writer would eventually produce the January 2026 IHRA piece when the stakes rose high enough.
Caldwell was always willing to criticize Trump on principle in public, starting from the first months of the second term, and that the later crisis essays are larger applications of the same principled critique he was making in March 2025 on a smaller scale. The consistency is visible from the first month forward.
The line about Trump being “the first president in history to punish a journalist for deadnaming” is a particular kind of Caldwell sentence. It uses the rival coalition’s vocabulary to criticize his own coalition’s leader. “Deadnaming” is woke-internal terminology for refusing to use a transgender person’s chosen name. Applying it to the AP’s use of “Gulf of Mexico” against the administration’s preferred “Gulf of America” forces the reader to see Trump’s punishment of AP as the same category of offense that woke activists commit when they police other people’s speech. The sentence does a lot of work. It would never appear in a pure coalition column because it would embarrass the coalition. It appears here because Caldwell is not writing a coalition column. He is writing an analytical column that happens to come down critically on a specific Trump policy. The willingness to use the rival’s vocabulary against his own side is what separates Caldwell from a pure coalition writer. The willingness is consistent across the arc, from March 2025 through April 2026. The presence of this willingness is what makes his writing interesting and trustworthy to readers across the coalition divide.
Caldwell is a principled writer whose principles produce criticism of any political project that violates them, including the project he otherwise supports. He began the Trump second term in March 2025 by criticizing the Gulf of America rename on free-speech grounds. He endorsed the DEI assault three weeks later because the policy was one he had supported for years. He continued this pattern of conditional endorsement across the following months, applying his analytical framework consistently even when it required him to criticize his coalition’s leader. The escalation of criticism from January 2026 onward was not a change of heart. It was a response to an escalation in the Trump administration’s provocations. The writing remained consistent in method. The events required increasingly serious applications of that method. The writer at the end of the arc is the same writer at the beginning, applying the same tools to increasingly consequential problems. The arc is the record of how that application played out across a year in which events forced the tools to produce increasingly direct criticism of the coalition Caldwell had otherwise been willing to support.
April 7, 2025: “How DEI destroyed itself.”
Caldwell writes:
Perhaps the most shocking thing to a foreigner about Trump’s early agenda is that it has been aimed at the institutions of civil rights set up in the 1960s and 1970s – the “nicest” part of a country that prides itself on its niceness. Government policies of racial remediation were not just enshrined in national mythology. They were also guarded (like most “nice” things) by a set of taboos that would imperil the careers of any who trespassed them. Within 48 hours of his inauguration, Trump had used a series of executive orders to abolish affirmative action, the linchpin of race-based law enforcement.
This was the sort of problem that, in his first term, left Trump befuddled. In his second term, he has proceeded with a sheer bureaucratic competence not seen since Franklin Roosevelt. Trump had a sense of where the regulatory pressure points of the civil-rights system lay: in its reliance on presidential regulation rather than law. He knew where the establishment was most vulnerable: in the economic dependence of race-driven academic departments and charitable foundations on streams of revenue that the White House could turn on and off.
The April 2025 DEI piece is the most important piece for understanding the arc, because it is the foundational pro-Trump essay that the later crisis essays will eventually be forced to question. This is Caldwell at his most full-throated in defense of the Trump second-term project. The essay celebrates Trump’s “sheer bureaucratic competence not seen since Franklin Roosevelt,” compares his regulatory moves favorably to what Machiavelli would admire, and explicitly approves of the redirection of civil-rights enforcement machinery against DEI and Woke. The Apocalypto epigraph frames the whole Woke apparatus as a civilization destroying itself from within, with Trump as the opportunistic conqueror who arrives after the self-destruction is already complete. The essay ends by explaining why Americans are not protesting: they have lived through 2020-2024 and drawn their conclusions.
Several observations follow.
First, the April 2025 piece contains the exact move that the January 2026 IHRA piece will later object to, and Caldwell in April 2025 endorses it. He writes approvingly that Trump “did not abolish” the civil-rights regime but “redirected its mighty regulatory powers against his political adversaries.” This is the procedural move of using rival-coalition administrative tools against one’s own opponents. In April 2025, Caldwell finds this Machiavellian genius. In January 2026, when Trump applies the same logic to the IHRA antisemitism definition, Caldwell names it as “an archetypal Trumpian gambit” that “triumphs in practice” but “loses in principle.” The shift is real and substantial. The same writer endorsing the same structural move in April 2025 objects to it nine months later.
In April 2025, Caldwell was willing to celebrate the redirection of civil-rights machinery so long as the targets were DEI programs and race-preferential systems he had long opposed. The symmetry only becomes operative when the machinery gets turned against targets Caldwell values, such as campus speech about Israel. This is not hypocrisy, exactly, but it does show that Caldwell’s commitment to procedural principle is weaker than his substantive policy preferences. He is fine with Machiavellian redirection when the policy result is one he wants. He objects to it when the policy result hits speech or targets he wants protected.
Second, the April 2025 piece is the pure pro-Trump Caldwell. There is no criticism, no reservation, no measured distance. Trump is the competent executive, the Roosevelt of the anti-administrative-state project, the leader who has identified the regulatory pressure points and the economic vulnerabilities of his adversaries and is dismantling them with efficiency. This is the most enthusiastic Caldwell writing about a sitting American president that I have seen in any of the pieces. A reader knowing only this essay would conclude that Caldwell was a dedicated Trump supporter with no significant reservations.
The contrast with the April 2026 Easter column is therefore as extreme as it gets. Both are April essays, exactly twelve months apart, and they describe different worlds. In April 2025, Trump is the executor of a historically significant project. In April 2026, Trump is a man whose Easter performances outrage the religious sensibilities of a stone, whose behavior requires recalculating “all our measurements of acceptable risk,” whose change of character over the past year makes him newly dangerous. The writer is the same. The subject is the same. The assessment is opposite. The year between them is the story the intellectual biography has to tell.
Third, the April 2025 piece uses the Aziz Rana citation in a striking way. Rana is a Boston College constitutional historian writing from a progressive perspective about the Trumpist “cultural assault on the basic creedal assumptions forged during the 20th century.” Caldwell takes Rana’s critical account and treats it as a useful description of what Trump is actually doing. He credits Rana’s insight that “the legitimacy of the civil rights regime is fragile.” This is Caldwell using a left-leaning scholar’s analysis to validate a right-wing project. The move is characteristic. Caldwell is always willing to engage serious work across coalition lines and repurpose it. In April 2025 he repurposes Rana to justify what Trump is doing. The same analytical generosity will later be directed at Pilkington, at Kokotajlo, at Wolff, at Zelizer. The writing always seeks the best available framework and uses it. In April 2025, the framework is Rana’s, and it supports Trump.
Fourth, the April 2025 piece establishes the starting position for the whole arc. Caldwell begins the year as a confident defender of the Trump second-term project. He treats the assault on DEI and civil-rights bureaucracy as overdue and welcome. He explains why the American majority is not protesting and endorses that non-protest. He treats Trump’s capacity for bureaucratic competence as historically significant. The subsequent twelve months will test this starting position against Trump administration actions. The January IHRA piece, the February Reiner piece, the February Nixon piece, the March obituary, the April Easter column are all reactions to events that complicate the original endorsement.
Caldwell is not purely a framework writer. He is a framework writer who, when his coalition is producing policy he likes, is willing to celebrate that policy even when its methods involve the same administrative-state moves he would criticize if the other side used them. His procedural principles are real but not absolute. His substantive policy preferences are weightier. When the policy is good, the procedural move is Machiavellian genius. When the policy is bad, the procedural move is a violation of first principles.
This is not a unique Caldwell flaw. It is close to universal among coalition intellectuals. The observation matters because it qualifies the earlier claim that Caldwell’s January IHRA objection was simply his civil-rights critique applied symmetrically. The symmetry is real but contingent. It required a provocation, namely Trump using administrative machinery to police speech Caldwell cares about, to activate. If Trump had continued redirecting civil-rights machinery against DEI targets Caldwell had always opposed, the symmetrical critique might not have emerged.
Second implication. The coalition-crisis register that dominates the January through April 2026 pieces is a response to provocations that accumulated beginning in January. The April 2025 Caldwell shows no signs of crisis because there was no crisis. Trump’s second term was doing what Caldwell wanted done, and Caldwell was celebrating it. The crisis that produces the later pieces was generated by Trump administration actions beginning with IHRA, continuing through the Reiner mockery, and intensifying through the Iran war and the Easter performances. Without these provocations, Caldwell might have continued writing in the April 2025 register.
Third implication. The Apocalypto epigraph in the April 2025 piece has an unintended resonance that the later essays make visible. Durant’s observation that “a great civilization is not conquered from without until it has destroyed itself from within” is applied in April 2025 to the civil-rights regime and American liberalism. Caldwell’s argument is that DEI’s excesses destroyed it from within and Trump’s assault is simply the external follow-through. But the same epigraph applies, with very little modification, to the Trump coalition itself. Trump’s character, his behavior around the Reiner murder, his Easter performances, his Iran war decisions, his Kushner-Witkoff foreign policy network, these are the internal destruction that no external opposition could have produced. Caldwell does not quote the Apocalypto line again in the April 2026 Easter column, but he could have. The line that justified the assault on civil rights in April 2025 applies just as well to the assault on Caldwell’s own coalition project one year later. A writer with more reflexive awareness would notice the parallel. Caldwell does not.
April 30, 2025: “The real battle for Europe.”
Caldwell writes:
The EU is a system by and for technocratic elites. During the 2008 financial crisis, Germany’s Angela Merkel and France’s Nicolas Sarkozy were able to use its institutions to overthrow the government of Silvio Berlusconi in Italy and block a referendum that would have led Greece out of the euro. The EU is mostly offstage, but it has mighty strings to pull. It plays the role that civil-rights law has for half a century in the US – offering a way for alumni of the better universities to review democratic decisions and freely entered private contracts. EU politicians like to call Brussels a “regulatory superpower.” That’s a boast.
This is a pro-Trump-administration column, written in defense of Rubio’s State Department cuts and Vance’s European policy, and framed as an explanation to non-experts of why the Trump-Brussels conflict is not about cultural hatred but about partisan alliance structures.
The thesis is that American and European progressive elites have spent decades acting as “partisan actors in the other’s politics” while assuming their populist opponents were too dim to notice. The EU functions for Europe as civil-rights law has functioned in America, as a mechanism for university-credentialed elites to override democratic decisions. Since the Clinton administration, the EU has been in alignment with the American Democratic Party. When Democrats are in power, Brussels and Washington combine to sanction, harass, and intervene against Hungary, Poland, and other anti-EU governments. When Republicans are in power, the EU works to deprive American Republicans of European allies. Rubio’s reorganization and Vance’s speeches are attempts to break up this trans-Atlantic partisan alliance. The whole confrontation, Caldwell argues, has nothing to do with “loving” or “hating” Europe. It is about dismantling a coalition structure that has operated against Republicans for thirty years.
This is Caldwell in carrier-group mode, but the carrier-group mode is not in crisis here. He is writing in defense of the Trump administration’s foreign policy in April 2025, and doing so clearly and confidently. The essay provides the theoretical framework that a Trump-sympathetic reader needs to understand why Rubio’s cuts are not vandalism and why Vance’s free-speech speech in Munich was not provocation. The framework is coalition analysis, and Caldwell applies it with his usual skill. The partisan-foreign-policy thesis is genuinely illuminating, and the EU-as-civil-rights-law parallel is a sharp observation that extends The Age of Entitlement arguments across the Atlantic.
Three observations follow.
First, the April 2025 Caldwell is unambiguously pro-Trump on the substantive policy questions. He defends Rubio’s State Department cuts. He defends Vance’s Munich speech. He presents the Trump administration’s European policy as a reasonable response to a real problem. There is no hint of the later character critique. There is no hint of the later procedural objection. There is no hint of the Catholic register that would come after the Easter 2026 provocations. In April 2025 Caldwell is a coalition writer helping his coalition’s administration explain itself to educated readers.
Second, the coalition work in April 2025 is cleaner than the coalition work in the later crisis essays because the coalition is not in crisis. Caldwell is defending the administration against its critics, not managing its internal contradictions. The prose reflects this. It is confident, organized, and free of the narrower registers that will characterize the February-April 2026 pieces. The piece is a good example of what competent coalition analysis looks like when the coalition is functioning. The later pieces are examples of what happens when the coalition starts producing its own embarrassments.
Third, the April 2025 piece shows Caldwell’s method at its most useful: naming an underlying structural reality that polemics on both sides obscure. The press narrative at the time was that Trump and Vance “hate Europe.” The European press narrative was that Americans “hate their values.” Caldwell reframes the whole conflict as a structural dispute over partisan alliance arrangements, which both narratives occlude. The reframing is correct in ways that reward a reader across the coalition divide. An anti-Trump European reader can accept the partisan-foreign-policy thesis without accepting Caldwell’s preferred resolution. A pro-Trump American reader gets a framework that explains his side’s policy without requiring him to endorse the emotional register of Trump’s own rhetoric. Caldwell’s service to his coalition is not flattery. It is clarification.
June 2, 2025: “Why everyone is talking about Bill Belichick.”
Caldwell writes:
Forty-nine years is an attention-grabbing age difference and Hudson is a force in her own right. Her father was a mussel-harvester in Hancock, Maine – which sounds like a vocation out of a different century. Environmental regulators apparently thought so, too. When they banned dredging in the local inlet, Hudson’s long-settled family became refugees of the Green Transition. Her agitation on behalf of displaced fishermen like her father has been truculent – almost Trumpian. She spent last Thanksgiving at Mar-a-Lago with Belichick and the President.
Hudson’s mother, meanwhile, moved to the gay resort town of Provincetown, Massachusetts, where she manages a sex shop.
Jordon Hudson’s father “became” a “refugee of the Green Transition” when environmental regulators banned mussel dredging in Hancock, Maine. Her “agitation on behalf of displaced fishermen like her father has been truculent, almost Trumpian.” Her mother “manages a sex shop” in Provincetown and a neighbor says Hudson “reaffirmed her belief that you should be able to love anybody you want, as long as it’s legal.” These sentences do coalition work without seeming to. The Hancock fisherman who loses his livelihood to environmental regulation and migrates to Trumpism is a Caldwell character type, familiar from The Age of Entitlement through the Europe pieces. The Provincetown sex shop and the Washington Post sentence about loving anybody are gently deployed coalition markers for readers who share Caldwell’s frame. A reader outside that frame might not notice the markers at all. The essay is politically loaded in a way that does not register as political writing.
Caldwell sustains a comic tone across an entire essay. The “SnapFace” detail is funny. The observation that Hudson “was a toddler, probably being silenced with a tablet (not in the old sense of Dramamine but in the new sense of an iPad)” is funny. The closing line about “a competitive time in the life of a very competitive nation” is funny. The humor is not incidental. It is the register in which the essay operates. Caldwell at full comic strength in June 2025 is the Caldwell who could write the October bully piece, the December Europe piece, and the December Boomers piece. The humor is a leading indicator of analytical confidence, and it is fully present here ten months before the Iran war obituary.
The Belichick piece contains a philosophical throughline that does not appear in the political essays but belongs to the same writer. The observation that “the core of excellence, in life as in football, is mistake avoidance” and that “winning comes from developing good habits that can be carried into any situation” is a conservative philosophical commitment. The value placed on habit, process, and humiliation as teaching tools is the same value that organizes Caldwell’s preference for inherited institutions over symbolic-analyst professional expertise. The Belichick philosophy, as Caldwell presents it, is the counterpart in the athletic domain of the classical education argument in the AI piece. Excellence requires the mastery of forms, built through repetition and constraint, that produce judgment available in unfamiliar situations. This is a continuous theme in Caldwell’s thinking across apparently unrelated subjects. Football and Latin operate on the same principle.
The essay’s treatment of Jordon Hudson is an Alliance Theory demonstration, though Caldwell is not doing it deliberately. He presents Hudson as a figure whose personal trajectory embodies the coalition tensions of the moment. Her father is a Hancock fisherman displaced by green regulation. Her mother runs a Provincetown sex shop and supports gay rights. Her own relationship with Belichick unites the older conservative America with the post-2000 online-native one. She attends Thanksgiving at Mar-a-Lago. She is “truculent, almost Trumpian” on environmental regulation. She also believes you should be able to love anybody you want. She is a coalition amalgam, and Caldwell sketches her as such with a mix of affection and bemusement. The portrait is more generous than most of Caldwell’s political writing because the frame is not political. Hudson is allowed to be a full person with cross-cutting commitments. The same generosity does not always appear when Caldwell writes about Trump voters or European populists. The Belichick piece, read carefully, shows that Caldwell’s moral imagination is capable of more than the coalition-crisis essays suggest. The capacity is there. The pressure of the later crisis narrows it. The narrowing is situational.
July 14, 2025: “In the age of AI, humans must keep learning.”
Caldwell writes:
Every technological revolution threatens to render certain human capabilities obsolete – or, rather, promises to do so. At the start of the Industrial Revolution, traveling long distances on foot and lifting heavy objects were considered two of the banes of human existence. Machinery would abolish them. Every American has seen “Jersey barriers,” those thin cement slabs laid end-to-end to separate lanes of traffic. In the 1950s, the New Jersey highway authority laid them down in the middle of small-town Main Streets to keep pedestrians from interfering with King Car. You could no longer pick up a newspaper and cross the street to read it in the coffee shop. No, you’d have to drive to the traffic light a quarter-mile away and double back. The New Jersey authorities could not fathom that anyone might want to cross a street, or do exercise of any kind.
The AI piece is the most quietly revealing essay in the sequence so far, because it shows Caldwell working on a subject that does not sit neatly inside any coalition. AI is a topic where the political right is divided between accelerationists and catastrophists, where the religious right is mostly still figuring out what it thinks, and where the usual coalition-intellectual moves do not quite fit. Caldwell uses this freedom well.
The essay’s argument is this. AI threatens to atrophy human cognition at the same moment AI becomes powerful enough that human cognition is needed to control it. The Industrial Revolution made walking and lifting obsolete as tasks, and they returned as hobbies through gyms and cycling. AI will make thinking obsolete as a task, and the argument is that thinking will need to return through something like deliberate education. The essay reviews Dario Amodei’s optimistic essay on AI’s civilizational potential, questions the wokeness of Amodei’s egalitarian framing, pushes back on Amodei’s claim that the socialist calculation problem is unsolvable by AI, turns to Daniel Kokotajlo’s darker AI 2027 paper for the counter-view, and closes with a defense of classical liberal education as the foundation of the kind of trustworthy judgment AI cannot be trusted to supply. The Kinks quotation at the end is a genuine surprise and works.
The AI piece shows Caldwell as a writer interested in serious intellectual problems that have nothing to do with American coalition politics. The subjects treated are Amodei’s essay, Kokotajlo’s AI 2027, the Hayek-Lange socialist calculation debate, the Tower of Babel, the pedagogical value of dead languages, and Matthew Crawford’s line about AI as a solution in search of a problem. These are the references of a serious person reading widely across genres. The essay could appear in Harper’s or The New Atlantis without revision. It does not read as coalition work. It reads as intellectual work.
The AI piece has one striking coalition moment. The paragraph on Africa includes the sentence “Africa is flourishing now. It will add a billion people to its population by the middle of this century. This owes less to the modern things it has than to the modern things it never got: feminism, psychoanalysis, near-universal contraception and advanced weaponry. No wonder mainstream culture holds the former ‘Dark Continent’ in such reverence.” This is Caldwell at his most right-wing, phrased in the cool aphoristic register that is his signature. The passage performs the coalition move of inverting mainstream moral valuation, treating African population growth as evidence that escaping modern Western institutions is a blessing, and putting “Dark Continent” in scare quotes to pretend distance from the phrase while deploying it. The move is coalition work performed inside what is otherwise an intellectual essay. Caldwell uses these moments sparingly and with craft. They are the markers that remind the reader this is a Spectator piece, not a New Atlantis piece.
This piece contains what may be the clearest statement in any of these essays of Caldwell’s positive vision, as opposed to his critical diagnoses. The closing argument for classical liberal education as the foundation of trustworthy judgment, “because it concerned a bygone time no longer blurred by change and no longer subject to the campaigning and imitation of interested parties,” is a Caldwell argument. It draws on his Catholic sense of inheritance, his European sense of the weight of tradition, his Americanist sense of the loss of shared cultural reference, and his long-standing skepticism of symbolic-analyst professional classes. It is the same cluster of commitments that will produce the later coalition-crisis essays, here stated in positive form rather than critical form. The AI essay shows what Caldwell is for, which the later essays show only obliquely through what he is against.
September 8, 2025: “Liberalism is a lost cause.”
Caldwell writes:
Pilkington views liberalism as earlier generations of political philosophers did: as one long process of replacing relations based on “status” with relations based on “contract.” Since the days of John Locke, the heart of the liberal idea is that every human being is free to make his own choices: why should I have to worship in the state church if Father X is preaching next door and I wish to listen to him?
Liberalism aims to increase happiness by smashing every rule and razing every institution that keeps individuals from contracting freely with one another. If we were all only individuals, that would be great. But we also belong to institutions that care for us and allow us to care for others – families, churches, fraternities – and liberalism has destroyed these as well.
The Pilkington review is a substantively different piece from everything else in the sequence. It is a book review, not an occasional column. Caldwell is working through another writer’s thesis at length, summarizing the argument, extending it in places, and adopting its framework as a lens on current events. The book review genre gives him permission to think structurally in a way the magazine column format does not. The result is the most theoretically ambitious piece in the run so far.
The core argument, in Caldwell’s presentation of Pilkington, is that liberalism is a long process of replacing status relations with contract relations, that this process requires ruthless enforcement to keep voluntary alternatives from re-emerging, that the contractual logic fails when applied to sex and reproduction, that this failure generates mass migration, generational conflict over democratic legitimacy, and a bubbling-up of alternative solutions like euthanasia, and that liberal elites cannot see the decline coming because their professional habit is to treat reality as manipulable perception. The essay closes with a Yeats echo about things falling apart and the center failing to hold.
This is the theoretical substrate for everything Caldwell will write in the subsequent months. The January IHRA piece is an instance of the ruthless-enforcement point. The February Reiner piece is an instance of the failure-of-perception-management point. The February Nixon piece is an instance of the legitimacy-decline point. The March and April pieces on Trump are instances of what happens when a coalition nominally opposed to the liberal order produces a leader whose methods mirror its worst habits. The Pilkington review establishes the theoretical frame that organizes the later crisis writing even when Caldwell does not explicitly invoke it.
The Pilkington review shows Caldwell still doing the kind of work that made him a serious intellectual rather than merely a political columnist. The review locates Pilkington inside a tradition that runs from Henry Maine’s status-to-contract thesis through Dangerfield through Colin Crouch. It treats the Ukraine war and the BRICS alliance as instances of structural shifts that long predate any particular American president. It treats deindustrialization as a long-running American policy choice rather than a partisan dispute. The frame is historical and structural. The American political crisis is one local symptom of a global transition.
The Pilkington framework is not Caldwell’s own in the narrow sense, but it fits his prior work closely. The Age of Entitlement argued that the 1964 civil rights regime created a rival constitutional order requiring continuous administrative enforcement against voluntary associations. Pilkington’s argument that liberalism requires ruthless measures to keep voluntary organizations from re-emerging is a generalization of the American case Caldwell made fifteen years ago. Caldwell adopting the framework is Caldwell finding his own argument extended and systematized by a younger writer. The review functions as endorsement and elaboration rather than engagement with a foreign thesis.
The Pilkington review contains the element that will prove most consequential for the later arc. The observation that liberal elites “have an almost magical belief in the power of perception” and that “their professional experience has convinced them that reality can be whatever you want it to be” is a theoretical observation in September. It becomes a practical indictment of Trump himself in April. The Easter column on the change in Trump is built around Trump’s Peale-ian inheritance, the idea that “perception is more important than reality,” and the way this belief produces an organization that generates alternate reality. Caldwell identifies the same habit Pilkington identifies in liberal elites and traces it in Trump. The later essay does not cite the Pilkington review, but the diagnostic tool is the same. Trump is, in this analysis, a product of the same cultural failure he was supposed to challenge. The Pilkington review supplies the theoretical frame that makes this critique coherent.
The September piece is notable for what it does not contain. There is no Catholic register. There is no character critique of any American figure. There is no coalition-management pressure visible in the prose. Caldwell is thinking about the global liberal order, its historical trajectory, and its structural contradictions. The thinking is long-frame and cross-coalition. If an editor at The New Republic or Foreign Affairs had wanted to run the review, they could have without changing a word. This is Caldwell at his most analytically unconstrained.
The Pilkington review makes visible the long-term intellectual project that organizes everything Caldwell writes, including the coalition-crisis essays. That project is the description of the post-1960s Western liberal order as a historical formation in decline. The September review states the project in its fullest theoretical form. The December Boomers essay states it demographically. The December Europe essay states it politically. The January through April essays state it in the form of what happens when the American right’s champion of the anti-liberal case turns out to practice the same vices. The coalition-crisis register is one mode within the project. The structural-historical register is another. The project is the same.
October 6, 2025: “The bully doctrine.”
Caldwell writes:
The Bully Doctrine boils down to this: the more threatening a person is, the less threatening he is. Where does this bizarre idea come from? Perhaps it is a holdover from an age of gentlemanly manners when, for instance, bragging about money was a sign you didn’t have any. Perhaps it comes from the age of Freud, when people understood human personality traits as compensations for deeply felt, hidden inadequacies. But it seems more likely that our ideas of bullying arise from stupid after-school specials and Disney films – and that we believe them out of wishful thinking. It’s a poor compass for navigating a dangerous time.
The bully piece is a pure example of what Caldwell does when he is working at full analytical range and not managing a coalition crisis. The essay is not about Trump in any primary sense. Trump appears as one instance of a larger phenomenon, which is the ideological construction of “the bully” as a political trope that licenses reckless foreign policy. The real subjects are Milošević, Saddam, Putin, and the American foreign-policy class’s habit of persuading itself that adversaries with actual capabilities will collapse under verbal pressure. The Kimmel incident at the top is a pretext for developing the argument.
The analytical method is vintage Caldwell. He notices a linguistic fact, the Google Ngram hockey-stick curve on “bully,” treats it as historical evidence, and traces the concept’s expansion as a function of political needs. The Cold War ends, the unipolar moment opens, and Washington needs a vocabulary for pushing others around without seeming to be the aggressor. “Bully” is that vocabulary. The word gets applied to Milošević, then to Saddam, then to Putin, then to Trump, then to Russia by the Obama-to-Biden-era advisors. The concept’s function, in each case, is to persuade the American political class that the target will fold under pressure. Caldwell points out that in each case the target has not folded.
This is excellent foreign-policy writing. Caldwell here is equally willing to apply the bully analysis to Trump as to Putin. His closing observation names the doctrine as poor compass regardless of who is using it against whom. He is not defending Trump from the bully charge. He is saying the charge itself is usually nonsense, on whichever side of the aisle it gets deployed. The Susan Rice quotation at the end, where she applies the doctrine to Trump, is treated with the same skepticism Caldwell applies to the Obama-era advisors who wrote it about Milošević and Putin.
The October bully piece is the second consecutive essay that centers Trump analytically without carrying any coalition-crisis weight. The November game-theory piece assessed Trump’s negotiating style with distance. The October bully piece treats Trump as one instance of a larger Washington pattern. Neither essay defends Trump. Neither attacks him. Both treat him as a phenomenon available for analysis. This suggests that the carrier-group register I identified in the February through April essays is not merely temporary but triggered by events beginning in January. The October Caldwell has no carrier-group register at all. He is writing as a foreign-policy commentator with access to a broader intellectual frame than his coalition’s current politics requires.
The bully piece contains a critique of American foreign policy that would have been out of place in the later crisis essays. The line about the Kosovo war being “the first interstate war in Europe since World War Two” launched “to discipline Serbian strongman Slobodan Milošević for his anti-terrorist actions in the province of Kosovo” is a strongly revisionist take on a conflict most of the respectable American press has treated as a humanitarian success. Caldwell’s revisionism is grounded in his broader skepticism of the post-1990 American foreign policy consensus. The Iraq War line, “the Iraq War that the younger Bush launched in 2003 has indeed gone down as a landmark in the history of bullying, though not for anything Saddam did,” extends the revisionism to the most important conflict of the neoconservative era. These are positions Caldwell has held for decades. They do not fit easily into a coalition-crisis reading because they are cross-cutting. The same writer who will later defend the anti-war wing of Trump’s coalition is here attacking the foreign policy record of the Weekly Standard milieu he came out of. This is intellectual continuity rather than coalition management.
The bully piece shows Caldwell willing to criticize Trump inside a frame that is not coalition-bound. “Whether or not you think Trump is a bully, both he and Moe must be reckoned with” does not defend or attack Trump. It simply grants that Trump is powerful and dismisses the rhetoric that pretends he isn’t. The framing allows Caldwell to make a real argument about Trump without having to decide whether he is a Trump defender or a Trump critic. He is neither and both, depending on the question at hand. This flexibility is what the later coalition-crisis essays lose.
November 5, 2025: “Is Donald Trump a game theorist?”
Caldwell writes:
A foreign trading partner could be forgiven for asking what good can come of making any concession to the United States at this point. Trump has decided to use the American role as the West’s defender to engage in hegemonic rent extraction, as game theorists put it. Or, as historians put it, to exact tribute. We now monetize everything, including solidarity. Humiliations result for our friends in Europe as well as for our rivals in Russia and China. This may well be a clever move in a dollars-and-cents way. It could revive American industry. It could even help balance the budget. But the problem for Americans is that humiliations and broken relationships have a cost, and it is one that is hard to calculate until it is too late. You don’t need to be a game theorist to know that.
Caldwell works on Trump while keeping some distance from both sympathy and critique. He plays the question as an open one. Could Trump be a sophisticated strategist? The essay considers the case, grants what must be granted, and names what is missing. The structure is neither defense nor prosecution. It is assessment.
The assessment is sharp. Caldwell credits Trump’s tariff approach with splitting potential trade adversaries through prisoner’s-dilemma logic, credits him with understanding the trade-relations paradox that deficit countries have less to lose at the negotiating table, and credits him with needing no Nixon-style madman theatrics because his real behavior does the work. Then he names the problem. A bargaining style built on credible threats is self-undermining because the more credible the threats, the less credible the promises. Trump’s hegemonic rent extraction generates short-term gains at the cost of long-term relationship capital. The humiliations have costs that are hard to calculate until too late.
This is Caldwell at his most analytically disciplined. The piece treats Trump as a phenomenon to be understood rather than a leader to be defended or attacked. It grants the possibility of unintuitive sophistication and then identifies the structural limits of the approach. The prose voice is calm and professional. There is no Catholic register, no character critique, no coalition defensiveness. This is the Caldwell who made his reputation writing for the Financial Times.
Two observations follow.
First, the November piece establishes that Caldwell was already naming costs in Trump’s governing style before the winter crisis sequence began. The game-theory essay ends on a concern about relationship costs that will prove prophetic for the later arc. “Humiliations and broken relationships have a cost” is the analytical point the December through April essays will extend into individual domains. In December, he applies it to the European leadership’s loss of credibility. In January, he applies it to the procedural costs of using rival-coalition tools. In February, he applies it to the moral costs of abandoning basic decencies. In March, he applies it to the coalition costs of the Iran war. In April, he applies it to the religious costs of Catholic sacrilege. The November essay supplies the through-line. Trump extracts short-term gains at costs that compound invisibly until they become visible all at once.
Second, the November piece carries less Catholic weight than any other essay in the sequence. The vocabulary is game theory, trade economics, and Cold War diplomacy. Nixon appears as a historical reference point for the madman strategy, not as the coalition carrier he will become by February. The essay could have been written by a centrist foreign-policy analyst with no particular religious or national-conservative commitments. This matters for understanding what happens in the subsequent months. Caldwell in November still has the full secular analytical range available to him. He uses it. The narrowing into Catholic and character registers that dominates the February through April essays is not a permanent feature of his writing. It is a response to pressures that emerge in January and intensify through the spring.
The analytical implication is important. The later crisis essays are not the expression of a writer whose frame has narrowed. They are the expression of a writer whose normally broad frame is being pressed into narrower registers by events. The November essay proves the broader frame remains available. The December and earlier pieces confirm it. What the crisis does is force Caldwell to deploy only part of his range at a time. When he writes the Catholic column in April, he is not limited to Catholic analysis. He is choosing Catholic analysis as the best available tool for the task at hand. When he writes the Nixon piece in February, he is not limited to historical rehabilitation. He is choosing it for an argumentative purpose. The limitations in the crisis essays are tactical rather than constitutive.
The game-theory piece also shows Caldwell engaging with his coalition from the inside without reflexive sympathy. Sarah Isgur, a former Trump administration lawyer, is quoted respectfully but not uncritically. Scott Bessent, the Treasury Secretary, is quoted with a slight edge. The essay asks whether Trump’s game-theoretic sophistication is real or whether his apparent strategic coherence is the result of others projecting theoretical frameworks onto his behavior. The question is left open. Caldwell does not decide it. The indeterminacy is honest. A coalition writer with looser standards would have decided it either way. Caldwell holds the question open because he genuinely does not know.
This is a kind of writing that almost disappears from the sequence after January. The later essays make decisions. The November essay refuses to. That refusal is itself a mark of analytical confidence. A writer who feels coalition pressure cannot leave questions open about his coalition’s leader. He has to take a position. The November Caldwell does not feel that pressure. The February and March Caldwell does. The April Caldwell has settled into a position that allows him to stop feeling it.
December 2, 2025: “Eclipse of the Boomers.”
Caldwell writes:
There is going to come a moment when the boomers’ political power falls below the threshold necessary to prop up this vision of things. It could happen before the next election. And then something is going to happen that no one has given much thought to: control over our politics and our culture is going to pass to a non-baby boom generation – perhaps a much younger one – that looks at the world in its own, totally different way.
The Boomers essay is not about Trump at all. It is a piece of historical-demographic analysis that treats the American political landscape as a function of age-cohort numbers. The argument runs: boomers dominated because they were demographically invincible, their governing assumptions became the nation’s common sense by force of numbers, and their numerical decline will lift those assumptions’ grip on American institutions. The three boomer tenets Caldwell lists (that slavery is the main thing in American history, that men and women are not much different, that youth is the best part of life) are identified as consensus positions held by no one in American history before 1968 and unlikely to be held by most non-boomers now. The essay predicts a shift in the governing vision as the generational weight passes.
This piece carries the other essays’ analytical framework but points it forward rather than at any political leader. It is the most structurally confident of the seven pieces. Caldwell is not managing a coalition crisis here. He is doing the kind of demographic and cultural analysis that made The Age of Entitlement distinctive. The prose is clean, the argument moves from data to claim without rhetorical strain, and the voice carries the cool authority his best work has always had.
Two observations follow.
First, the December 8 essay and the December 22 Europe essay together establish a writer at ease with his craft. Neither piece is managing internal coalition pressure. Neither requires the Catholic or character registers that the later pieces deploy. Caldwell is writing about demographic succession and European political failure with full analytical range, and the prose shows it. The boomer piece is funny in its opening paragraphs, concrete in its middle, and sober in its close. The Europe piece has the 10 Downing Street soul-shake image and the mutton-chop sideburns line. These are writer-at-top-of-form touches that disappear once the Trump coalition crisis begins in January.
Second, the Boomers essay prefigures the later arc in a way Caldwell may not have fully seen. His three boomer tenets are the ideological apparatus of the post-1964 civil-rights regime he spent The Age of Entitlement anatomizing. If the boomer generation is losing demographic grip on American institutions, the regime those tenets sustain is entering a transitional period. Caldwell’s constitutional argument, as developed across the essays, depends on this transition being real. His Nixon rehabilitation, his critique of the administrative state, his opposition to IHRA speech regulation, his entire theoretical program only makes political sense if the boomer consensus is in fact losing its grip. The December 8 essay supplies the demographic foundation for the constitutional argument the later essays advance.
The Boomers essay also has a small but telling observation that connects to the later Caldwell. When he writes that boomers “quarrel over the details of this vision, but not over its basic tenets,” he names something important about coalition intellectual life. The dominant consensus is sustained not by agreement on everything but by agreement on the basic tenets that make everything else debatable. This is, without Caldwell naming it, a description of what carrier-group intellectuals do. They quarrel over particulars while sustaining the basic tenets that make the coalition’s vision seem like common sense. Applied to the American right, the observation has the obvious uncomfortable implication. A conservative intellectual coalition that quarrels over Trump’s character and policies while sustaining the basic tenets of unitary-executive constitutionalism, anti-administrative-state critique, and civilizational pessimism is doing what Caldwell’s own boomers do in his description. The quarrels are real. The tenets remain.
Caldwell does not notice this parallel. A writer applying his own framework symmetrically would have to notice it. The fact that he does not is itself data about the limits of carrier-group self-awareness.
December 17, 2025: European leaders on Ukraine.
This piece is the baseline the later arc departs from. In December, Caldwell is still writing as a sympathetic observer of the Trump foreign policy. The essay credits Trump for pushing Zelensky toward negotiation, treats European war enthusiasm as delusion rooted in domestic political failure, treats Putin’s casus belli as at least partly vindicated by the revelation of American operational support for Ukraine, and reads the whole European posture as the giddiness of wartime command filling a void left by failed governance. The sympathies here are classic national-conservative anti-war, and Trump is on the right side.
The January IHRA essay, read against this December baseline, becomes the first registered crack. In December, Trump is the adult urging negotiation while European leaders perform Churchill cosplay. In January, Trump is a president using rival-coalition administrative tools against his own dissenters. The shift is sharp. It is not that Caldwell has turned against Trump. It is that he has identified the first thing about Trump’s governance that he cannot endorse from inside his own principles. The IHRA move is procedurally wrong for reasons Caldwell’s own civil-rights critique already established.
The December essay is also worth looking at on its own terms because it reveals a kind of writing Caldwell does well that does not appear in the later pieces. The soul-shake image at 10 Downing Street, the Mad Lib Zelensky speeches, the mutton-chop sideburns line at the close, these are moments of visual wit that carry real analytical weight. The mockery of European leaders is not cheap. It is grounded in the statistical reality Caldwell marshals: 13 percent growth in Europe since 2008 versus 87 percent in the US, no significant role in AI, a 6 percent French deficit, AfD and National Rally polling as largest parties. The witty opening earns the serious analysis that follows. The later pieces are more restrained and less funny. The December piece shows what Caldwell’s prose can do when he is not managing a crisis inside his own coalition.
The deeper observation is that Caldwell’s diagnosis of the European leadership is one he will not apply to his own position six weeks later. He writes in December that European leaders, having lost their claim to historical inevitability, retreat into the giddiness of wartime command because it offers “the only context in which they can speak as leaders of the people.” This is a sharp piece of Alliance Theory analysis, though he does not call it that. Elite class loses legitimacy, reaches for a substitute performance, and mistakes the performance for the reality. When he writes the Trumpism obituary in March, Caldwell himself reaches for an obituary performance that substitutes for coalition reality. The diagnosis he applies to Macron in December is one he falls into himself in March. He does not notice the parallel.
Alliance Theory predicts this kind of blindness. Writers who apply structural analysis to their rivals rarely apply it to themselves in real time. Caldwell sees Macron’s bluster as a cover for European political failure. He does not see his own March obituary as a cover for his own coalition’s continuing hold on its base. The December piece shows him at the top of his analytical form. The March piece shows him making the same kind of error he just diagnosed in others.
One further observation is useful. The December piece shows Caldwell still making use of the Ukraine war framework without signs that the war is about to force him to choose between subfactions inside the American right. The January IHRA piece, the February character pieces, and the March obituary all occur after the pressure begins. The Ukraine essay belongs to a calmer period. It is worth noting that this calmer period existed as recently as late 2025 and that Caldwell’s analytical discipline was fully available to him in it. What broke the discipline was a sequence of Trump administration actions, beginning with the IHRA policy in late 2025 and culminating in the Iran war in March 2026. The Caldwell of December is the Caldwell who could do this work with full analytical authority. The Caldwell of March was operating in crisis conditions.
January 9, 2026: IHRA and free speech.
Is it anti-Semitic to “accus[e] Jewish citizens of being more loyal to Israel, or to the alleged priorities of Jews worldwide, than to the interests of their own nations?” It might well be anti-Semitic to generalize about Jews in that way. But it’s not unheard of for Christians or Muslims to care more about their co-religionists than their compatriots, and there would be nothing anti-Semitic about acknowledging cases where the same is true of Jews. Other examples sound as if they were written simply to stifle discussion: is it anti-Semitic to claim “that the existence of a State of Israel is a racist endeavor”? Such accusations of racism are indeed tedious – but we have just been through an entire generation in which everyone has been stigmatized as a racist for everything. Israel is hardly being singled out. And if it’s anti-Semitic, as the definition claims, to practice “double standards” – to care about Gaza more than Xinjiang – then politics becomes impossible, because such value judgments are what politics is about.
You can see why Mamdani might be uncomfortable with the IHRA definition: he is a longtime supporter of the Palestinian cause. Under such a definition, he and his friends can be dismissed as anti-Semites, whether or not their attitude toward Middle Eastern politics has anything to do with their attitudes toward Jews.
The break with Trump is not primarily about character and not primarily about Iran. It begins with a policy disagreement over the use of antisemitism definitions to police campus speech. Caldwell’s January essay treats Trump’s adoption of the IHRA definition as “an archetypal Trumpian gambit” that “triumphs in practice” while “surrendering the moral high ground.” The key sentence is that it “clears out a space for dissenters of the last generation” but “loses in principle, surrendering the moral high ground to dissenters of the next.”
This is the Caldwell of The Age of Entitlement talking, and what he is saying is not small. He is accusing Trump of doing what the civil-rights regime did. The pattern Caldwell spent a career anatomizing, smuggling law into society piece by piece through foundation-authored definitions that regulators and judges then treat as benchmarks, is now being practiced by the Republican administration against its own opponents. Trump is using the IHRA definition the way post-1960s liberals used the civil-rights regime. The tools are the same. The coalition using the tools has changed. Caldwell’s objection is that the tools themselves were wrong when liberals used them and are wrong now that conservatives use them.
This is a significant piece of intellectual honesty. A lesser coalition intellectual would have let the IHRA move pass without comment on the grounds that it was hurting the coalition’s adversaries. Caldwell names it as the same procedure he spent twenty years opposing. The objection is procedural rather than substantive. He does not say Trump is wrong to oppose campus antisemitism. He says Trump is wrong to use the administrative tools of the rival regime to do it. A principled unitary-executive conservatism cannot operate that way without becoming the thing it claimed to oppose.
The Mamdani frame is interesting. Caldwell uses a Ugandan-born Muslim socialist mayor as the unlikely hero of a free-speech moment. The opening paragraphs perform the gesture the piece requires: concede that Mamdani is woke, concede that he is hostile to Israel, concede that his comments about Netanyahu are hair-raising, concede that his Democratic Socialists chapter tweeted things on October 7 that support the “supporter of terrorism” charge. Then credit him with striking “a powerful blow against political correctness” because he revoked the IHRA order. This is Caldwell finding dignity where his coalition does not expect him to find it. He makes the same move he made for Trump voters and European populists: he grants moral standing to a figure the respectable consensus treats as dangerous.
The piece also shows Caldwell willing to cross his coalition on Israel policy. The IHRA definition is defended by every major American Jewish organization, the Trump administration’s State Department, the ADL, and the Federalist Society’s dominant line on campus free speech. Caldwell calls it “a catastrophe for freedom of speech.” He walks through the seven politicized examples and dismantles them one by one. The argument that treating criticism of Israel as antisemitism “stifles discussion” and makes “politics impossible” is the standard anti-IHRA case, and Caldwell makes it without hedging. This is one of the clearer pro-Palestinian campus free-speech arguments available in the respectable right press. It comes from a Catholic national-conservative writer at The Spectator, not from a left-leaning journal.
Alliance Theory reads this piece as an early indicator of Caldwell’s subfaction position within the larger coalition. The American pro-Israel evangelical Christian Zionist wing of Trump’s base is the faction most invested in the IHRA definition. Caldwell is writing against that faction and in favor of the anti-war national-conservative Catholic faction whose signature positions are skepticism of open-ended Middle East commitments and resistance to speech regulation. The split inside Trump’s coalition that would become visible over Iran in March was already visible in January over IHRA. Caldwell was already writing from one side of it.
This also explains the Reiner essay more fully. The character argument in February was the moral complement to the procedural argument in January. In January, Caldwell objects to Trump’s use of the rival regime’s administrative tools. In February, he objects to Trump’s lack of the moral qualities a principled unitary-executive conservatism requires. The two critiques work together. A president who both uses his opponents’ tools and lacks the character to deploy his own with restraint is a president who cannot carry the constitutional argument. The Nixon rehabilitation eight days after the Reiner piece now reads as the logical next step. Caldwell had named both the procedural problem and the character problem. The constitutional theory needed a different carrier. Nixon was available.
Caldwell has been working in public on the problem of how a national-conservative Catholic intellectual should relate to an American president who represents the movement’s policy victories and betrays its moral and procedural commitments. He has been doing this work in print, one piece at a time, with visible care. The January IHRA essay is the opening statement and also the least Catholic of the five. It is written from the free-speech right of the old conservative tradition. The later pieces add the Catholic register and the character register. The IHRA piece is the procedural core around which everything else organizes.
February 6, 2026: The Reiner case and character.
The Reiner essay is already doing Catholic work before the Easter column makes it explicit. The key sentences run: “When decent people speak of someone who has just died, they understand that they are in the presence of God or, if you prefer, eternity.” This is Caldwell’s natural vocabulary. The presence of God, the dwarfing of earthly preoccupations, the respect for human life as a precondition of governing. The Easter column looks less like a sudden Catholic turn and more like the culmination of a Catholic register Caldwell has been using all along. The religious frame preceded the Catholic controversy. Trump’s Jesus image was the event the Catholic register was waiting for.
Second, it recasts the Nixon essay. If Caldwell was already worried about Trump’s character on February 16, the Nixon rehabilitation on February 24 looks more deliberate. He was not writing in a calm theoretical mood that the Iran war would later interrupt. He was writing as a man who had already named his leader’s character problem in print, eight days earlier, and who needed a historical anchor for the constitutional argument before the character problem fully discredited the live American carrier. The sequence I gave you earlier treated the Nixon piece as prescient. A better word is strategic. Caldwell had noticed the wobble before the public did. He used the Rosen revelation to lodge the theory in a safer location while the live carrier was still operating but already suspect.
Third, the Reiner essay itself shows the Alliance Theory problem you flagged earlier, in a cleaner form than the Iran obituary. Caldwell names Marjorie Taylor Greene as the representative Trump-sympathetic voice registering the damage. MTG is a stranger witness for his case than he seems to realize. She was pushed out of the MAGA inner circle months earlier for reasons mostly unrelated to policy. Caldwell treats her reaction to the Reiner mockery as evidence that Trump’s sympathizers are turning. She is not a typical sympathizer. She is a recently excommunicated one, whose freedom to speak freely is a function of her exclusion rather than her representativeness. A writer applying Alliance Theory with care would note that the witnesses available to register internal discontent with a coalition leader are typically the ones the coalition has already purged. Their testimony is biased by their position. Caldwell uses her as a bellwether for the broader Trump coalition. She is not a bellwether. She is a disgruntled former insider, which is a different sociological category.
The essay is also interesting for what Caldwell concedes — the ICE’s policy case. He concedes the numbers on public support for deportation. He concedes that governing kills people and that this is a burden democracy must accept. He concedes extenuating circumstances in both Minneapolis shootings. The concessions are strong and explicit. Then the essay pivots: the policy is right, the political support is there, the operational outcomes are defensible, and yet the campaign is showing signs of having been discredited. His answer is character. Trump’s conduct regarding the Reiner murder broke something that policy and public support cannot repair.
This is the most Catholic argument in the piece, though he does not flag it as such. The claim is that a political project depends on moral conditions that exceed the political. A president who cannot observe the decencies owed to the dead cannot be trusted to calibrate the acceptable risk of government operations that kill people. The character failure contaminates the operational judgment. A reader who shares Caldwell’s underlying theological framework finds this argument natural. A reader who does not share it finds it either sentimental or moralistic.
The Alliance Theory reading sharpens here in a way my earlier analysis undersold. Caldwell is not just registering a break. He is attempting to establish the grounds on which a break from Trump is legitimate without being a betrayal of the coalition’s policy goals. The Reiner essay does this work more carefully than either the obituary or the Easter column. It keeps the policy case intact. It concedes what must be conceded to the base. Then it isolates character as the only necessary point of departure. This is the most strategically considered of the four pieces because it is the earliest. He was thinking carefully about how to structure the break before events forced him to make it.
What we now have is a four-piece arc that reads as a coalition intellectual managing a leader problem over two months.
On February 16, Caldwell identifies the character problem through the Reiner case. The policy case is defended. The theological vocabulary of the presence of God is introduced quietly.
On February 24, Caldwell lodges the constitutional theory in Nixon’s rehabilitation. This is insurance for the argument against the possibility that the live carrier cannot carry it.
On March 18, after the Iran war, Caldwell writes the obituary. The character break is now a coalition break, and he treats the movement as finished. This is the least strategically controlled of the four, the most reactive, the one where Alliance Theory most clearly catches him substituting his subfaction’s view for the coalition’s view.
On April 17, after the Easter performances, Caldwell writes the change-has-come piece in fully Catholic terms. The theological register introduced in February is now explicit. The coalition is separated from the man.
Read in order, the arc is coherent. It shows a writer who identified the character problem early, built a historical fallback for the theory, over-read the Iran war as the final break because it lined up with his own subfaction’s priorities, and then settled into a Catholic-national-conservative register that gave him a stable vocabulary for distancing himself from Trump while keeping the coalition’s constitutional argument alive.
The Reiner essay is the most impressive of the four on its own terms. It is also the one that makes the Iran obituary look like a loss of judgment rather than a natural next step. Caldwell in February was writing with care and restraint about a character problem whose political consequences he correctly refused to overstate. Caldwell in March lost the restraint and predicted coalition death that did not come. Caldwell in April recovered some of the February poise, but within a narrower religious frame. The February piece shows what he can do at his best. The March piece shows what he does when events briefly overwhelm his analytical discipline. The April piece shows him settling into a sustainable position for the long run.