What We Can Learn About Trump from Henry VIII

It's a loyalty test. It's always a loyalty test.

I’ve been following the Trump-Pope showcase showdown while traveling these last few weeks in the U.K. and E.U. I’m not sure this is the smartest fight for him to pick, politically speaking, but in the end, I’m not sure his goal is to actually win against the Pope. I think it’s to get his followers to abandon their faith in anyone else but him. In other words, it’s a loyalty test, and he’s not the first one to make people choose between him and the Catholic Church.

Probably like a lot of readers of this Substack, I went down the whole Tudor England rabbit hole a few decades ago when Philippa Gregory’s historical novels about the period came out; I also read Alison Weir’s The Six Wives of Henry VIII (nonfiction, and excellent), the first two books of Hilary Mantel’s trilogy (the last one is still on my shelf), and a ton of BBC docuseries about the period. This is why, at the beginning of Trump’s first term, I wasn’t the only one struck by how he shared many personality traits with the former monarch. I mean, leaving aside that Henry VIII was very erudite and also quite creative — two characteristics Trump definitely does not have — he was also a narcissist, tyrannical, vengeful, mercurial, eventually totally out of shape, and, of course, a huge womanizer. (Big “grab ‘em by the p**** “ vibes.) I think what reminded me of Henry VIII the most in Trump’s first term was how he would fire people: He’d do it by tweet or through the press (like with Comey), but never in person. That was how Henry VIII treated two of his wives, including Anne and later Catherine Howard, when he was done with them — just had them arrested and taken to the Tower, while he went off hunting or with his new mistress.

There were other parallels that I can’t remember anymore — we’re well past Tudor England and in Crazytown Hellscape now, so I don’t think about it much these days (though others still are). But the whole Pope thing happened while I happened to be doing some research on oaths, including Henry VIII’s Oath of Succession and Oath of Supremacy. Henry required his subjects to take these oaths after he divorced his first wife, Catherine of Aragon, a move not condoned nor recognized by the Church. He got around this proscription by basically telling the Pope to take the L and making himself the head of the Church of England, and getting Parliament to pass two acts to ratify his break with the church and legitimize his marriage to Anne. These acts mandated the respective oaths: the Oath of Succession acknowledged Henry’s heirs with Anne Boleyn as legitimate, and the Oath of Supremacy recognized Henry VIII as the head of the Church of England.

I’ve been researching oaths because I’m interested in what kinds of moral codes best constrain behavior. It turns out that oaths are pretty powerful in this regard — people take oaths pretty seriously, perhaps because they can’t be entirely certain that they won’t be called to account in the afterlife for transgressing it, even if they aren’t on earth. To that end, Henry VIII knew what he was doing when he forced his two oaths on his subjects: Choose. Me over the Pope. Pretty much everyone did.¹ One of the few who didn’t was one of Henry’s closest advisors, Thomas More. Upon his refusal, he was accused of treason, tried, and executed. (Very Trumpy!)

[Incidentally, the play/movie A Man for All Seasons, about Thomas More’s arrest and trial, also has the following perfect exchange on the rule of law which is also apropos of our time:

William Roper: ‘So, now you give the Devil the benefit of law!’

Sir Thomas More: ‘Yes! What would you do? Cut a great road through the law to get after the Devil?’

William Roper: ‘Yes, I’d cut down every law in England to do that!’

Sir Thomas More: ‘Oh? And when the last law was down, and the Devil turned ‘round on you, where would you hide, Roper, the laws all being flat? This country is planted thick with laws, from coast to coast, Man’s laws, not God’s! And if you cut them down, and you’re just the man to do it, do you really think you could stand upright in the winds that would blow then? Yes, I’d give the Devil benefit of law, for my own safety’s sake!’]

Anyway, Trump hasn’t made his cabinet, members of Congress, or his supporters swear an oath of loyalty to him…yet. But this fight with the Pope may as well be one, and Trump’s minions are obliging. Two days ago, Pete Hegseth compared Trump to Jesus, while House Speaker Mike Johnson criticized the Pope for “wading into political waters.”

But I suspect the loyalty test was mainly for Vice President J.D. Vance, who has been teasing his new book, Communion, which is set to be released in June. It’s hard to tell whether for Trump this is mainly a loyalty-test-as-humiliation-ritual, or loyalty-test-to-tank-JD’s-chances-to-be-president, or loyalty-test-because-this-will-be-the-ultimate-show-of-subservience…or some combination of all three. Whatever it is, J.D. has passed with flying colors, warning the Pope to “be careful” and to “stick to matters of morality.”

I have no doubt that as the tests escalate, everyone around Trump will continue to fall in line. However, they would be wise to look at the long list of people in Henry VIII’s inner circle who were executed (I counted 54). In the end, loyalty wasn’t what saved them — it was what did them in.

1. I looked up how many others refused to take the oaths and the only ones I could find were Bishop John Fisher and 18 Carthusian monks from the London Charterhouse.