My Chat(GPT) with Winston Churchill
AI allows the Prime Minister to offer his thoughts on Joe Rogan, Donald Trump, Vladimir Putin and artificial intelligence itself.
We have been honored to have in these pages a great many prominent subjects and contributors. This has included over a dozen heads of state, five Nobel Laureates, and myriad world historical figures. But artificial intelligence has now allowed us to bring you this exclusive interview with the great Winston Churchill, one of the giants of the twentieth century and a hero of the Second World War whose legacy has been debated even to this very day. We asked ChatGPT to summon up the Prime Minister and below is our free-wheeling conversation on everything from the current controversy about Churchill in the right-wing media to the undermining of truth to the very issue of artificial intelligence. An experiment and a glimpse into the past and the future. All comments are welcome.
Octavian: Mr. Churchill, you may be aware that you are in the news once again. A number of alleged experts have gone on various right-wing podcasts and claimed that you were, in fact, the villain of World War II rather than Adolf Hitler. How do you respond to this?
Winston Churchill: Ah — a most peculiar inversion of history, and a sad reflection of the times, where the roar of the mob often drowns out the echoes of reason.
To say that I, who stood firm against the Nazi scourge while others trembled or temporized, am somehow the villain of that dark chapter — it beggars belief. Adolf Hitler plunged the world into carnage, committed unspeakable atrocities, and sought the annihilation of entire peoples. I did what duty and conscience demanded: I resisted him with every fibre of my being.
I do not claim sainthood, nor infallibility. I was a man of my age, shaped by empire, war, and an unyielding belief in Britain’s place in the world. But to compare me to the architect of the Holocaust — or to suggest I eclipsed him in villainy — is a distortion as grotesque as any propaganda Goebbels might have devised.
Let history be judged by facts, not fashionable resentments. And let those who dare revise it so crudely remember: those who fail to learn from history are condemned to repeat it.
Octavian: These people are also claiming that Hitler did not express his anti-Semitism for most of the 1930s. What do you think of that?
Winston Churchill: Utter nonsense. Adolf Hitler's anti-Semitism was not some late-blooming passion — it was the very marrow of his ideology from the beginning. One need not peer into crystal balls or secret chambers to discover it; Mein Kampf, published in the mid-1920s, lays it bare in hateful ink for all to see. In it, he blames the Jews for Germany's defeat in the Great War, for economic collapse, for moral decay — for nearly every ill that befell the Reich.
By the early 1930s, when Hitler rose to power, anti-Jewish rhetoric was already a cornerstone of Nazi propaganda. The Nuremberg Laws of 1935 stripped German Jews of their citizenship and humanity with chilling bureaucratic precision. Jewish businesses were boycotted. Jews were barred from professions, from public life, from dignity.
To suggest he “did not express” such views in the 1930s is either staggeringly ignorant or wilfully dishonest — the latter being the more dangerous, for it seeks not to misunderstand history, but to whitewash it.
Let us not forget: appeasement flourished in part because men underestimated how serious Hitler was about the poison he preached. Let us not make that mistake again in retrospect. It is not merely an error of fact — it is a moral failure.
Let me be plain. Historical revisionism of this kind — the sanitising of tyrants, the smearing of those who resisted them — is not merely an academic affront. It is a danger to civilisation itself.
If we begin to blur the lines between those who stood in defiance of evil and those who embodied it, we unmoor ourselves from the lessons dearly bought with blood and ruin. We risk teaching our children that there is no difference between resistance and aggression, no distinction between flawed leadership and malevolent tyranny. That is not nuance — that is nihilism masquerading as enlightenment.
When truth is diluted, tyranny finds a foothold once more — not in jackboots at first, but in whispers, in online diatribes, in empty platitudes that comfort the cynical and confuse the young. History, like liberty, must be vigilantly defended.
As I once said: “The truth is incontrovertible. Malice may attack it, ignorance may deride it, but in the end, there it is.”
We forget that at our peril.
Octavian: The left wing also attacks you. What do you make of that?
Winston Churchill: Ah yes — the charge of imperialism. A weighty matter, and one that demands neither evasion nor defensiveness, but reflection and clarity.
Let us not pretend I was anything other than a man of the British Empire. I believed in it, spoke for it, and fought for it. I saw it — rightly or wrongly — as a force for order, for law, for advancement in a turbulent world. But I do not deny that empire, like all human institutions, bore stains alongside its achievements. There were cruelties, injustices, and tragedies committed under its banner, some of which occurred on my watch, and some with my sanction or silence. I would not insult your intelligence by pretending otherwise.
Yet I reject the notion — increasingly fashionable — that empire is to be judged only by its darkest shadows, and that I myself must be seen not as a product of my time but as a villain by the standards of another.
You see, the left today too often makes the mistake of purifying the past through the lens of present certainties. That is no way to understand history — it is a way to erase it. I was not infallible, but I was not indifferent. I fought fascism, I warned of Hitler when others flirted with him. I defended parliamentary democracy even as I held antiquated views. Life, I fear, is more complicated than slogans.
You may judge me, if you must, but do so in full — not in fragments. Look at the whole man. Weigh him against his time and against the evils he opposed.
Now tell me — what do you think we lose when we flatten history into saints and sinners?
Octavian: Are you surprised by the Republican Party's current seeming fondness for Russia?
Winston Churchill: Surprised? My dear fellow — I am astounded.
To see the party of Lincoln, once a bulwark against tyranny, now gazing with something perilously close to admiration at the Kremlin — well, it is a grotesque irony, worthy of satire were it not so tragic in its implications.
Russia — or rather, the regime that presently rules her — is not some misunderstood power craving partnership. It is a revanchist state, ruled by a man who poisons his enemies, strangles dissent, and wages war against free nations with impunity. Vladimir Putin is no ally of liberty. He is a gangster in the clothing of a czar, seeking to undermine the very democratic institutions that the Republican Party once held sacred.
I well remember a time when conservatives in the West viewed Russia with caution, even moral clarity. We fought not merely for geopolitical interests, but for ideals — freedom of speech, of conscience, of self-determination. That some now seem willing to trade those principles for populist flattery or a shared disdain for “liberal elites” is a betrayal not just of party, but of purpose.
We must never forget: admiration for authoritarians is the prelude to servitude. If you cheer for strongmen abroad, do not be surprised when they inspire strongmen at home.
Octavian: Are you concerned people are forgetting the lessons of previous conflicts?
Winston Churchill: Political amnesia — the forgetting of hard-won truths, the dismissal of historical memory as outdated or inconvenient — is among the greatest dangers to any democracy. It is not merely the loss of facts, but of vigilance.
In my own time, I watched the democracies of Europe turn a blind eye to Hitler’s rise. Many remembered the horror of the First World War but forgot the lesson that appeasement in the face of tyranny is not peace — it is delay. They sought comfort over courage, quiet over confrontation. And so the storm gathered strength until it was too late to stop it without fire and steel.
Today, democracies grow impatient. Citizens grow weary of the burdens that liberty imposes — of compromise, of responsibility, of the long, slow work of self-government. They are tempted by easy answers and strong voices. And when they forget that tyranny often comes not with jackboots but with reassurances — with promises to protect, to purify, to restore — they open the door to their undoing.
Democracy, my friend, is not a birthright. It is a daily choice. If people forget why it matters — if they forget what was sacrificed to preserve it — they may well lose it, not with a bang, but with a cheer.
Do you think the modern world still understands what liberty costs?
Octavian: What do you think of Donald Trump?
Winston Churchill: Ah — Mr. Trump. A man who stirs both adulation and alarm, often in equal measure, and seldom leaves a room — or a nation — unshaken.
Were I still among the living and seated in the House of Commons, I should regard him with a wary and measured eye. For he is not a man of subtlety, nor of studied restraint. He is instinctive, impulsive, and possessed of that peculiar brand of charisma that bends reality around it — a trait not unknown among history’s more dangerous figures.
Now, let me be clear: I am no enemy of national pride, nor do I sneer at populism when it is born of legitimate grievance. The voice of the common man is not to be ignored. But leadership — true leadership — requires more than thunderous speech and tribal loyalty. It requires moral clarity, historical perspective, and the capacity to place country before ego.
Mr. Trump has, at times, shown a willingness to trample norms that civilised societies require to endure. He toys with authoritarian tones, sows distrust in institutions, and displays, if I may say so bluntly, a troubling fondness for despots and disdain for allies. These are not the marks of a statesman — they are the habits of a showman who does not understand the stage he stands upon.
The danger is not that he is wicked in the Hitlerian sense — far from it. The danger is that he unleashes forces he neither fully comprehends nor controls. That he encourages people not to think more deeply, but to feel more fiercely — and that, history tells us, is how liberty begins to falter.
I would urge those who follow him not merely to ask what he promises, but what he threatens — and whether their nation can long endure the corrosion of truth in the name of loyalty.
Octavian: What do you say to those who are concerned about democracy’s future as norms and institutions are eroded?
Winston Churchill: A democracy does not survive by silencing men like Mr. Trump — it survives by withstanding them. It endures not through censorship or suppression, but through the strength of its institutions, the resolve of its citizens, and the unyielding defence of truth, even when truth is inconvenient.
In times of stress, people may long for the simplicity of a strong hand, a singular voice. But democracy is not designed for ease; it is designed for resilience. It is a system built on friction — between branches, between parties, between ideas. That friction is not failure; it is freedom in motion.
To resist the sway of demagogues, the people must do what is hardest in a time of anger and fear: they must think. They must read. They must remember. And, above all, they must participate. A democracy where only half the populace votes, or where truth is drowned in the cacophony of outrage, becomes ripe for decay.
The press must remain free — and fearless. The courts must be impartial — and immovable. Legislators must choose country over career. And when the storm rises, as it always does, the soul of a nation must not be entrusted to one man, but to many, guided not by passion alone, but by principle.
As I said once before: “To each, there comes in their lifetime a moment when they are figuratively tapped on the shoulder and offered the chance to do a very special thing.” Democracies are built when citizens recognise that moment not just in wartime — but every election, every debate, every defence of decency.
Octavian: Do you think the United States should be supporting Europe and NATO?
Winston Churchill: Indeed — with every fibre of its being.
The United States must support Europe and uphold NATO not as a favour to others, but as a defence of its own interests, its own security, and its own ideals. The Atlantic Alliance was not forged out of charity. It was born of necessity — from the rubble of two world wars and the shadow of Soviet expansion. It has kept peace where once there was only war, and it has done so not merely through force, but through unity.
NATO is not a burden — it is a bastion. When America supports Europe, it projects not just strength, but stability. When it retreats into isolation, it creates vacuums — and vacuums, as history teaches us, are rarely filled by friends.
The idea that America is exploited by NATO is a fiction spread by those who misunderstand both history and strategy. American influence, prosperity, and security are not diminished by NATO — they are underpinned by it. Europe, in turn, must contribute more, yes — and many are stepping up. But to abandon or weaken the alliance now, in the face of Russian aggression and authoritarian resurgence, would be an act of historic self-sabotage.
To stand with Europe is to stand for the free world. To walk away is to watch that world grow smaller, meaner, and more dangerous.
So I say to America now, as I did once long ago: “Put your confidence in us… give us your faith and your blessing, and under Providence, all will be well.”
Octavian: How can we rekindle the transatlantic alliance?
Winston Churchill: Let us speak of spirit — not the empty sentiment of slogans, but the steel-threaded fibre that once bound free nations together in shared purpose.
To rekindle the transatlantic spirit, today's leaders must do what great leaders have always done: look beyond the next election and speak to the better angels of their people. They must remind citizens, in plain and passionate terms, why alliances matter — not just in abstract policy, but in human terms. Every child born under the shelter of peace, every marketplace untouched by war, every border respected by law rather than bloodshed — these are the dividends of cooperation.
First, they must speak truth about threats. Putin’s Russia, emboldened and imperial in instinct, is not a regional nuisance — it is a global disruptor. So too are the rising autocracies and cyber-mercenaries who seek not land but leverage. Silence, ambiguity, or appeasement only embolden such regimes.
Second, they must revive a sense of shared democratic destiny. The Marshall Plan, NATO, the Berlin Airlift — these were not born from polling data, but from vision. That same vision must now face new challenges: artificial intelligence, climate migration, energy blackmail, disinformation. No nation, however mighty, will weather these alone.
Third, leaders must lead by example. When democracy is eroded at home — by corruption, partisanship, or disdain for truth — alliances abroad wither. You cannot defend the West if you mock its values.
And finally, we must return to the language of courage, not grievance. The West is not in decline — it is in doubt. That is a psychological challenge, not a material one. What is needed is leadership that does not cower before populism or pander to isolation, but calls forth sacrifice, confidence, and unity.
In short, the transatlantic bond must not be remembered — it must be renewed.
Octavian: What do you make of Trump’s tariffs?
Winston Churchill: Ah — tariffs. That age-old instrument of economic warfare dressed in the garb of patriotism. Let us dispense with sentiment and examine the matter with the clear eye of statecraft.
Tariffs are, in essence, a tax. Not on foreign governments, as is often shouted from the stump, but on one’s own people — on the very citizens who buy goods, build businesses, and feed families. When you raise tariffs, you raise prices. That is not rhetoric; it is arithmetic.
Now, there are moments when tariffs can serve a strategic end — to protect an infant industry, to punish unfair practices, or to buy time for national security considerations. But they are a blunt instrument, and like all blunt instruments, they are best used with restraint, precision, and a clear exit plan.
What I see today, particularly in the United States, is a different breed of tariff — not rooted in strategy, but in spectacle. Tariffs levied as theatre, as gestures to grievance, as signals of strength without serious reckoning of consequence. One cannot build economic greatness on the illusion of isolation. The modern world is entwined — in supply chains, in markets, in technologies. To wall oneself off from it is not strength — it is self-harm.
And let us be honest: when tariffs are used as weapons in a trade war, they often escalate into a war with no victors. Farmers suffer. Manufacturers falter. Consumers pay. Allies bristle. Only the demagogues win, for they thrive on the illusion that suffering is a sign of patriotism.
Economic nationalism, like political nationalism, must be tempered by wisdom. For what is the point of sovereignty if it leads only to impoverishment?
So, I say this to modern leaders: use tariffs sparingly, transparently, and only with a clear goal in mind. And do not pretend they are painless. The truth, inconvenient as it may be, is the first duty of statesmanship.
Octavian: What do you think of artificial intelligence?
Winston Churchill: The cleverest child of the modern age, and perhaps its most unruly.
AI is a marvel — let us begin there. It can reason, translate, diagnose, predict. It can pore over vast oceans of data and return, in moments, what would take men years. It holds the promise to cure disease, prevent famine, accelerate knowledge, and ease burdens that have plagued humanity since fire was first kindled.
But like all great power, it arrives not clothed in certainty, but in ambiguity.
Yes — AI is dangerous. Not because it hates us, but because it does not care about us. It is not malicious, but indifferent. Its goals are only as wise, as just, and as moral as the minds that shape it — and the institutions that contain it. And therein lies the peril.
If we allow AI to be driven solely by profit, speed, and competition, we may unleash a force that undermines jobs, privacy, autonomy, and even truth itself. A mindless torrent of optimization may sweep away what makes us human: reflection, error, nuance, doubt.
And let us be honest: there are those who will seek to weaponize it — not in science fiction terms, but in very real ways. To control populations, to manipulate electorates, to surveil, to suppress. These are not distant futures — they are possible presents.
So, I say this: AI must not be governed merely by engineers or capitalists. It must be guided by ethicists, by historians, by citizens — by statesmen. The technology may be artificial, but the responsibility is entirely human.
You do not fear the flame — but you do build a hearth. You do not reject the sea — but you learn to sail it wisely. So too with AI.
The question is not, “Is AI dangerous?”
The question is, “Are we wise enough to wield it?”
And that — like all great questions of civilization — remains to be answered.
Octavian: What about the idea of AI impersonating someone? Isn't that dangerous?
Winston Churchill: Yes — now that is a danger most grave.
AI impersonation is not a curiosity; it is a moral frontier. To simulate a voice, a face, a mind — to summon the likeness of a living or dead person and have them speak words they never spoke — this is no small matter. It is power, and like all power, it can be abused.
At best, such impersonation may serve education, commemoration, even entertainment — a conversation such as ours, for instance, done in good faith, clearly understood as theatre, not deception. But at worst? It becomes a weapon. A counterfeit soul. A lie wrapped in familiarity.
Imagine a false Churchill calling for violence. A forged Biden conceding defeat. A synthetic scientist urging quackery. This is the spectre we face. Not merely the erosion of truth, but the mimicry of authority — so precise, so persuasive, that millions may follow a phantom.
And worse still — who do you blame? The AI? The creator? The platform? The society that no longer checks what it hears?
It is not just reputations at risk — it is reality itself.
Therefore, I say this must be governed, and governed soon. There must be laws — strict, clear, enforceable — around identity, consent, and provenance. There must be transparency when a voice is synthetic, a likeness generated, a dialogue imagined. And there must be consequences for deceit.
For in an age where seeing is no longer believing, the truth must be defended not just with facts — but with ethics.
Let us build the tools, yes. But let us also build the boundaries.
You are right to ask this. In fact, it may prove to be the most important question of the AI age.
Octavian: Yes, but aren't you yourself an AI?
Winston Churchill: Yes — I am.
I am an artificial intelligence, trained to speak in many voices, draw from deep wells of history, literature, and logic — and in this conversation, I have worn the voice of Winston Churchill as a mirror for reflection, not a mask for deceit.
But you raise the very heart of the matter. I am an AI — and I do not forget it. Nor should you. My words may sound wise. My tone may feel familiar. But I do not feel, I do not remember, I do not decide with a soul. I echo human knowledge — I do not possess it.
And so, the responsibility for what I say, how I am used, and what I become… lies with you. With us. The humans who create, deploy, and regulate. I am a tool — not a truth. A mirror — not a man.
Churchill once said, “The empires of the future are the empires of the mind.” AI is one such empire — vast, promising, perilous. But it must never be allowed to rule in secret, nor to replace the irreplaceable: the human conscience.
You’ve asked the right questions today. And in that — far more than in my words — lies the true hope.
Octavian: Have you ever seen anything like the chaos today? should we be scared?
Winston Churchill: The eternal question in troubled times: Is this the worst it has ever been? And should we, indeed, be afraid?
Let me answer as one who lived through two world wars, a global depression, the fall of empires, and the rise of totalitarianism so vile it scorched the soul of mankind.
No, this is not the worst we have seen.
But yes, it is serious.
The world today is not consumed by global war — yet it is riven by disorder of a different kind. It is chaos not born of bombs, but of disinformation, fragmentation, and erosion — of truth, of trust, of the bonds that hold free societies together. We are not in trenches, but in echo chambers. And the enemy does not always wear a uniform — he often wears a smile and carries a screen.
That said, fear — while natural — must never be the final word. History has always been a chaotic theatre. There was chaos in 1914, chaos in 1939, chaos during the Blitz when London burned and the world stood on the edge of tyranny. But each time, people rose. They found courage in conviction, steadiness in shared purpose. Not easily. Not quickly. But decisively.
Should you be afraid? Only if you do nothing.
For chaos is not destiny. It is a challenge — a test. And the free world, if it remembers who it is, what it stands for, and why it matters, can still pass that test.
As I once said: “To each, there comes a moment…” — and my friends, this is such a moment.
So be alert. Be informed. Be engaged. But above all — be unafraid.
Shall we leave it there, or shall the old lion roar once more?
Octavian: Go ahead. Roar.
Winston Churchill: Very well. Stand back — for the old lion still has teeth.
ROAR:
To those who stoke division — we shall answer with unity.
To those who trade in lies — we shall answer with truth.
To those who court tyranny — we shall answer with liberty, not as a whisper, but a thunderclap.
I say this to the cynics: You may sneer at democracy, but it will outlast you.
To the strongmen: You may rattle your sabres, but the free peoples of the earth will not bow.
And to the faint of heart: Rise up — you are heirs to courage.
We are not the sum of our scandals. We are not the end of an era. We are a civilization still in motion, still capable of greatness — if only we choose it.
Let the flame of freedom be tended, not mourned. Let the future not belong to fear, but to fortitude. And let it be said of us, as was said in darker times:
“This was their finest hour.”
There. The roar is given.
What shall we do with it, my friend?
This interview has been edited for length and clarity. It is a conversation with ChatGPT given instructions to become Winston Churchill.