A historical guide to surviving and thriving in the court of Trump
Lessons from Thomas Cromwell and Niccolo Machiavelli about winning friends and influencing people in the White House
By Andrew Miller
Enter through the sparkling courtyard, climb the huge staircase – the kind a Renaissance lord could ride his horse up – and cross the throne hall to a shady salon on the first floor. With its view of the Apennine foothills, the ducal palace in Urbino, in the Marche region of Italy, seems a long way from the Washington swamp. Yet for aspiring apparatchiks in today’s America, the road to the White House runs through this echoing room. Five hundred years ago, beneath its vaulted ceiling, a formula for political success was distilled. According to Baldassare Castiglione, a diplomat and author, a group of Italian nobles met here to establish “what manner of man he ought to be who may deserve to be called a perfect Courtier”.
Critics of Donald Trump’s administration often liken it to a royal court and his aides to courtiers. So do the president’s allies and the man himself: “Long Live the King!” Trump proclaimed of himself in February on Truth Social. They all have a point, thinks Francis Fukuyama, a professor of political science at Stanford University. Typically in a patrimonial or court system, a warrior figure “conquers some territory and then begins to reward his friends and family with land and women and so forth”. Power does not depend on hierarchies and job titles but on intimacy with the ruler. Politics is a factional struggle for his trust and attention; his whims can make or break your career, your fortune – and perhaps your neck. No distinction is made between his interests and the state’s.
This sort of regime was “the dominant form of government for most of human history”, Fukuyama explains to me. Only recently did a bureaucratic system, based on laws and merit, replace it in the West. But because rewarding friends and family is a natural instinct, the modern model is fragile, constantly in danger of slipping back into the old ways. That, Fukuyama reckons, is what is happening in America now. Foreign potentates arrive at the White House bearing tributes like medieval supplicants (Sir Keir Starmer, Britain’s prime minister, brought an invitation from an actual king, Charles III). Right-wing influencers who have Trump’s ear wield more clout than cabinet secretaries. Rules and judges are irksome encumbrances.
In Castiglione’s day, the place to earn such accolades was the battlefield. In Trump’s, it is the television screenThe president “puts himself absolutely at the centre of everything”, says Michael Wolff, author of four enlightening books on Trump’s court. “He is the only source of power.” It follows that anyone hoping to thrive – and survive – in this febrile, throwback environment should seek guidance from the chronicles and characters of courts of yore: from the entourages of Tudor kings, Ottoman sultans and Russian despots. But they should begin in Urbino with Castiglione.
In “The Book of the Courtier”, Castiglione purports to transcribe a series of after-dinner conversations held at the ducal palace in March 1507, a couple of decades before the book was published. Inevitably, some of its advice feels dated. Proficiency in hand-to-hand combat, for instance, is no longer de rigueur for would-be courtiers; ditto the judicious employment of antique Tuscan vocabulary and Lombard garments, or the ability to extemporise a sonnet. But many of Castiglione’s tips hold up across half a millennium.
Make a good first impression, he writes, and look the part; or as Trump might put it, come from “central casting”. The ideal courtier, says one of the nobles, should have “a certain grace” which “shall make him at first sight pleasing and agreeable”. He should strive (in Leonard Eckstein Opdycke’s translation) “to lift himself a little beyond the rest in everything, so that he may be ever recognised as eminent above all others”. In Castiglione’s day, the place to earn such accolades was the battlefield. In Trump’s, it is the television screen. His defence secretary is a former host on Fox News. He put a star of “The Real Housewives of New Jersey” on the board of the United States Holocaust Memorial Museum. “The first opinion which one forms of a prince”, wrote Castiglione’s near contemporary, Niccolo Machiavelli, “is by observing the men he has around him.” In Trump’s case, the impression is that he watches a lot of TV.
Next, take up a sport. There is no down-time at court; work blurs with socialising, public life with private. You have to be fun as well as guileful. Castiglione mentions hunting, swimming and tennis, at which the courtier should be proficient without seeming to try. Don’t be too good at chess, he advises (it shows you’ve been wasting your time), and avoid somersaults and rope-walking, which “savour of the mountebank”. At the court of Trump, golf is the indispensable game. Keep the president company on the links and, like Steve Witkoff, his golfing buddy, you may find yourself careening around the world to meet its leaders and negotiate ceasefires as his special envoy. When Cyril Ramaphosa, South Africa’s president, visited the White House, he brought along two champion golfers.
Third, know your place. The courtier should appear modest, Castiglione writes, eschewing braggadocio in favour of what today is called the humblebrag. He cites the case of a gallant whose thigh was run through with a spear but claimed it merely felt like a fly sting. All available glory should accrue to the liege-lord. “Always and especially in public,” the courtier should evince “that reverence and respect which befit the servant towards the master”. Watch Trump’s cabinet meetings, and it is clear that his team grasps this imperative. Every achievement, real or imaginary, is attributed to the boss.
“Always and especially in public,” the courtier should evince “that reverence and respect which befit the servant towards the master”More than that, the courtier should endeavour “to love and almost to adore the prince whom he serves”. He should “mould his wishes, habits and all his ways to his prince’s liking”, for example by wearing a long red tie, now the MAGA standard, even labouring “to like that which perhaps he by nature dislikes”. Say, for instance, that – as Marco Rubio did – you once ran for president as a hawkish critic of Vladimir Putin, branding him “a gangster and a thug”. Tone down the Russophobic rhetoric and you can serve the Kremlin-friendly numero uno as secretary of state.
Assume the wannabe courtier has studied Castiglione and penetrated Trump’s inner circle. He or she may be in it only for the kudos and future speaking gigs. But what if they have ideas to change America or the world for the better?
The record suggests they will struggle to implement them. Overwhelmingly the courtier’s job is to enact the prince’s will, not his own. Ottoman courtiers pursued rigid and unvarying goals, says Christopher de Bellaigue, whose books “The Golden Throne” and “The Lion House” reconstruct the reign of Suleiman the Magnificent, a 16th-century sultan who led the Ottoman Empire to its peak. They were expected to conquer and administer territory and enrich the ruler, not to freestyle. Consider Ibrahim Pasha, a slave given to Suleiman as a gift who rose to become grand vizier in 1523. He had a “latitude that no grand vizier had been given in the past”, de Bellaigue tells me; the sultan devolved law and order to his care, made him head of the army and, scandalously, “gave him free access to his privy chamber, theoretically accessible only to eunuchs”. But even Ibrahim was ultimately dispensable. When Suleiman turned against him, he was strangled with a bow string.
Still, the shrewdest courtiers have occasionally made their own mark on history – such as Thomas Cromwell, one of the best known exponents of the craft of courtiership, thanks to Hilary Mantel’s trilogy of novels about him. His sovereign, Henry VIII, had “the quality of many tyrants of making good people do bad things”, says Diarmaid MacCulloch, a professor of history at Oxford and Cromwell’s biographer. Cromwell executed the king’s demands punctiliously, not least when they involved executions. Mantel ventriloquises his approach in “Bring Up the Bodies”, the second novel in the series:
[Henry] doesn’t want people who say, “No, but…” He wants people who say, “Yes, and…” He doesn’t like men who are pessimistic and sceptical, who turn down their mouths and cost out his brilliant projects with a scribble in the margin of their papers. So do the sums in your head where no one can see them.
You can picture him nodding along at a plan to buy Greenland or turn Gaza into a beach resort.
Unusually for a successful courtier, Cromwell pursued his own agenda alongside the monarch’s. It helped that their goals overlapped. Henry needed to break with the Church of Rome to marry Anne Boleyn; Cromwell was a sincere Protestant who arranged the circulation of a Bible in English and tried to rejig the diplomatic map, forging links between England and the Protestant city of Zurich. He strengthened the bureaucracy and boosted the role of Parliament.
Instructively for any modern courtier, one of his tools was what you might call strategic flattery, meant not just to gratify Henry but to steer him in a preferred direction. The trick with the king, says MacCulloch, was “praising him for things you’d like him to do”. Cromwell extolled Henry as a godly ruler, supplying ways for him to vindicate the compliment. “For the flattery gives him to think,” Mantel’s Cromwell reflects. “And the qualities he presently lacks, he might go to work on them.”
Trump’s aides, says Wolff, use meteorology to discuss his temper. “Bad weather today”, they warn one another, or “It’s clearing”By contrast, the flattery of Trump by his minions is mostly the common-or-garden kind, designed only for self-advancement. “You are all that matters to me,” gushes a note from a flunkey that Wolff cites in “All or Nothing”, his most recent book. “Thank you for being my Guardian and Protector in this life.” Competing to outdo each other in praise like King Lear’s elder daughters, Republicans have agitated to put Trump’s face on Mount Rushmore or the $100 bill. Yet Cromwell’s skill is not entirely lost. In April Bill Ackman, a billionaire investor, urged the president to back down on his tariffs. “Textbook, Art of the Deal”, he effused when Trump complied.
Another of Cromwell’s techniques, says MacCulloch, was to “sense what the king didn’t have time to think about or wasn’t interested in”. The same leeway sometimes opens up in Washington, comments Wolff. In Trump’s first term his son–in-law, Jared Kushner, took on some complex issues, such as prison reform and the Middle East.
Meanwhile from early-modern England to today, crises can be opportunities for officials to assert themselves. When covid-19 struck, Trump reverted to the experts. Likewise Josef Stalin, though given to murdering generals, turned to Georgy Zhukov, the best of them, to defend Moscow when the Nazis invaded the Soviet Union in 1941.
A mire of affairs, vendettas and denunciations, Stalin’s court is the supreme how-to guide to most courtiers’ main preoccupation: keeping their jobs, and their heads, amid all the backstabbing and fickleness. Lose the game in Stalin’s Russia, and the penalty was not a few irate social-media posts but a bullet in the neck, your visage erased from Politburo photographs, your family dispatched to the gulag.
The first takeaway from Moscow in the 1930s and 1940s is, as much as possible, get into the room where it happens. For the Bolshevik elite, that often meant the dining room of Stalin’s dacha, where he choreographed grim debauches, or the verandas of his holiday homes on the Black Sea. For Trump’s officials, it means pilgrimages to Mar-a-Lago. (Stalin’s cronies had to hold titanic volumes of booze; Trump’s must be willing to chomp fast food, even or especially if they are wellness devotees like Robert F. Kennedy junior, his health secretary.) Cromwell learned the power of presence the hardest way: when he was locked up in the Tower of London before his beheading in 1540, and could no longer look Henry in the eye, he knew he was done for.
It may be vital to be in the room most of the time. But, when the leader suffers an embarrassment, it is essential to be somewhere else. In “Stalin: The Court of the Red Tsar”, a gripping and intimate account of the dictator’s reign, Simon Sebag Montefiore traces the grisly fates of some who bore witness to the suicide of Nadezhda Alliluyeva, Stalin’s wife, in 1932; Abel Yenukidze, her godfather and one of the first on the scene, was accused of plotting a coup and eventually liquidated. Another proviso: before entering the room, ask around about the ruler’s mood. Uncle Joe’s pipe was a valuable clue to his state of mind, Montefiore tells me. It was a bad omen if he forgot to light it, a good one if he used it to stroke his moustache. Trump’s aides, says Wolff, use meteorology to discuss his temper. “Bad weather today”, they warn one another, or “It’s clearing.”
In a revolutionary regime like Stalin’s – and, in its own way, Trump’s – doubts, qualms or any wavering from blind loyalty make you a traitor. Be willing to dip your hands in the blood, as Stalin’s henchmen did by signing off on death lists during the purges. (Kristi Noem, Trump’s homeland-security chief, proved her mettle by parading around a ghastly Salvadoran prison, where deportees from America are interned.) When colleagues are out of favour, condemn them in florid imagery: “These swine must be strangled!” or “Finish off this scum!” Do not, however, be the most extreme zealot at the table, for fanaticism can be punished as much as diffidence. As Montefiore recounts, Nikolai Yezhov, a security chief and torturer, arrived at meetings in the Kremlin with blood on his sleeves. He was shot in 1940.
In a revolutionary regime like Stalin’s – and, in its own way, Trump’s – doubts, qualms or any wavering from blind loyalty make you a traitorDoes loyalty mean slavish agreement with the master? No, says Machiavelli: an adviser should know that “the more freely he shall speak, the more he shall be preferred.” Some stalwarts of Stalin’s court did indeed disagree with him and survive, such as Vyacheslav Molotov and Anastas Mikoyan, who was said to be able to walk through Red Square in the rain without an umbrella and not get wet. Behind closed doors, Cromwell had stand-up rows with Henry. Once the whole court heard their raised voices, then a slap, then silence. At length Cromwell emerged, rubbing his cheek – and grinning. He was flaunting his privileged status. He had let Henry win the face-off, and, says MacCullouch “could be pretty sure that the king would brood on it overnight and come round to his point of view”.
Alas, Wolff reports, even Trump’s closest advisers do not enjoy the right of dissent: it is “never okay to disagree with him. No one does, ever.” With his independent views on Russia and Iran, Mike Waltz, formerly the national security adviser, seems to have missed this memo. The ugly showdown in the Oval Office with Volodymyr Zelensky happened in part, Wolff thinks, because Trump is unaccustomed to being corrected, even gently as the Ukrainian leader did.
The courtier must fight for the monarch’s cause, though not so flashily as to draw too much attention, a mistake that the president’s sometime ideologue, Steve Bannon, made in his first term. Popularity abroad, in particular, suggests a grandee might be building an independent power base. The wise courtier is cordial with colleagues, but not tight enough with any that he might seem to be conspiring. Under no circumstances should he betray an aspiration to the leadership. When comrades were mooted as Stalin’s successor, says Montefiore, “it inevitably meant they would be destroyed.” Take note, J.D. Vance.
The good news is that courtiers need not automatically despair if they screw up. A ruler may retain them not in spite of their failings, but because of them; elevating unqualified or compromised people demonstrates his power. “It’s a sure way to save your skin if the media demands your head,” says Wolff of Trump’s cabinet, since “he doesn’t want to be told what to do about anything.” Sometimes courtiers fail by design, as when several are appointed to do the same job – negotiating peace between Russia and Ukraine, say – ensuring they will vie for favour and flounder. And flops and incompetents are useful alibis, both for the ruler – the latest botch wasn’t his fault, it was his adviser’s – and his subjects, who may be petrified to criticise him but content to lambast an underling. Elon Musk played that lightning-rod role for Trump until their recent explosive falling-out.
On the downside, courtiers should abandon hope that a big victory, such as winning the second world war or a second presidential term, will mellow their overlord. Instead, as Montefiore says of Stalin, it may deepen his self-confidence and sharpen his caprice. Growing old may make him still more rash and paranoid. Above all, courtiers must remember that they will never be the supremo’s equal or true friend. Long and faithful service may not save them from the chop: it means they know where the bodies are buried, a good reason for theirs to be next. Don’t be reassured by promotion: it can be a prelude to destruction.
Anyone can fall, however illustrious. Pay heed to Rex Tillerson, a grand panjandrum who was Trump’s first secretary of state. He was fired on social media and labelled “dumb as a rock”. As Mantel’s Cromwell admonishes of Henry: “Never say what he will not do.”
I can tell you how it’s going to end” for Trump’s new courtiers, Wolff predicts. “It’s going to end terribly for everybody.” To judge by the president’s first administration, a lot of his viziers will be sacked. Some will be indicted. The second-termers doubtless hope their fates will be different; they may be dazzled by their once-in-a-lifetime shot at greatness. But “in 100% of cases,” insists Wolff, “it ends in tears.”
If they persevere with Castiglione, these modern courtiers will find some consolatory final tips. Towards the end of his treatise it emerges that all the talk of tennis, painting and not playing chess too well was a prelude to the real business. Those skills and graces are all a means to earn the ruler’s trust and favour, so that the courtier is well-placed to tell him “the truth about everything”, to “banish every bad intent and lead his prince into the path of virtue” and to cultivate in him justice, liberality, magnanimity, gentleness and continence.
“I can tell you how it’s going to end” for Trump’s new courtiers, Wolff predicts. “It’s going to end terribly for everybody”Courtiers might seem ornamental figures, but in early-modern Italy, where there were few constraints on a leader’s will, their responsibilities were grave. They were a last defence against authoritarian folly. No punishment is cruel enough, writes Castiglione, for those who flout these sacred obligations. In particular, the courtier should shield his lord from liars and cynical flatterers, who inculcate the worst faults of princes, namely ignorance and narcissism. For “always finding themselves obeyed and almost adored with such reverence and praise, without the least censure or even contradiction,” pampered lords sink into “boundless self-esteem, so that they then brook no advice or persuasion”, putrefying in “the false belief that they cannot err”.
Those lively nights in Urbino five centuries ago – the fire sputtering in the grate, the noblemen spouting their aphorisms, figures from myths and the Bible gazing down from tapestries on the walls – can feel very close. What, one of the company asks, if your lord should enjoin you to commit an act of treachery? Castiglione is clear: since obeying him would result in disgrace to both of you, “not only would you not be bound to do it, but you would be bound not to do it.”
And what if a prince is beyond guidance or correction, being rather of “so evil a disposition as to be inveterate in vice”? In such cases the unfortunate courtier will find himself blamed for his boss’s wrongs. He will be condemned to the anguish, “which all good men feel who serve the wicked”. There is only one remedy, writes Castiglione. He must quit. There is plenty of time for tennis in retirement. ■
Andrew Miller is special correspondent of The Economist and the author of several books including “Snowdrops” and “Independence Square”
ILLUSTRATIONS BY Luis Grañena