Henry VIII and Donald Trump: More alike than not?

Henry VIII and Donald Trump are probably two of the most famous men in history… but don’t tell them that or we’ll never hear the end of it. On the surface, I didn’t think they would have much in common, but there was more there than I thought.


Both are second sons, so were not intended to inherit their father’s empire. Henry’s older brother Arthur died, as did Trump’s. Trump’s brother, Fred Jr, died of alcoholism, leaving Trump to take over the family business. Both men ascended to positions of power at a young age, and spent a lot of money that their fathers had saved for them. Both use this money to build their own personal empire, deploying the ancient art of propaganda.

Personality and Propaganda

Henry commissioned a painting by Holbein, featuring himself, his mother and father, and Jane Seymour. In contrast to his son, Henry VII looks weak and feeble, and is seen leaning on a pillar. Henry wants to be better than his father and uses artistic propaganda to perpetuate this image. Written on the pillar on which Henry VII leans, the text is inscribed: ‘the son was born to a greater dynasty.’ Henry spent more money on lavish jousting tournaments and builds 60 palaces just because he could.

Copy in oils of the Whitehall Mural, commissioned by Charles II in 1667. Artist: Remigius Van Leemput.

Trump’s version of this, is to become the president of his father’s, Fred Trump’s, construction empire. Trump bought a lot of property, and to build his own personal brand, stamped his name all over it. Trump opens a gaming industry, casinos, naming one ‘Trump’s Castle.’ He clearly thinks he’s the King. He then opened Trump tower in 1983. Basically, the modern equivalent of lots of paintings, right? There’s a degree of showmanship on both sides here.

Advisors and Governing

Trump and Henry also had the ability to make and break their advisors. Henry had Wolsey and Cromwell, and initially, Trump had Roy Cohn, who was feared throughout Manhattan. In both incidences, both Trump and Henry made their advisors and gave them a degree of power. This means that Wolsey, Cromwell and Roy Cohn all completely depended on those that they served, and if they should cross them… well two out of the three ended up losing their heads. Steven Bannon masterminded Trump’s campaign, and I don’t know about you, but I haven’t seen him anywhere near Trump recently, as he was fired. Henry himself was responsible for 300 executions, and both Henry and Trump appear to govern by fear. Trump has his finger on the ‘nuclear’ button, Henry could cut off heads. Trump noted that his administration was ‘different,’ and warned people not to ‘underestimate’ him, or they will be met with ‘fire and fury.’ Scary stuff. Dominic Sandbrook argues that both Henry and Trump have encouraged a hyper nationalism, ensuring that those who they govern are focused on their country and their country alone, we see this in Trump’s slogan ‘Make America Great Again.’

First Marriage

Trump and Henry both have had tumultuous relationships with women. Both men also don’t like to be upstaged by their wives either. Catherine of Aragon and Henry married in 1509, and had a happy marriage. She even used to sew his shirts by hand. On one occasion, while Henry is away, Catherine fends of a Scottish invasion, noting that the battle was ‘worth more than anything you could achieve in France.’ Catherine’s success outshone Henry’s in France, which probably did not go down well. 500 years later, Trump fell for Ivana Zelnickova, who he later left her in charge with refurbishing and relaunching the Plaza Hotel. Judging by the video footage, Trump is there as an accessory at the opening party, and he doesn’t exactly look happy. With Ivana at the fore, perhaps Trump also felt upstaged.


Both men would go through some messy divorces. Henry cast Catherine of Aragon aside in favour of Anne Boleyn, and formally separated from the Roman Catholic Church in order to marry her. This was a very public divorce battle, with Catherine of Aragon, at one point, openly storming out of the divorce court. Trump follows suit by having a very public affair with Marla Maples, which leads to a messy divorce battle with Ivana. Both of these don’t last though, as Anne’s marriage with Henry sours after a riding accident in 1536, which leaves him cantankerous and lacking mobility. Henry’s lack of activity makes him pile on the pounds, eating 5000 calories a day. Anne’s three miscarriages exacerbated the already strained relationship between the pair. All of this culminates in Anne’s execution, in May 1536, which was carefully crafted by Henry’s advisor Thomas Cromwell. Trump and Mala’s relationship also deteriorated, when the papers reported that the pair were regularly have fierce arguments, partly because of Trump’s unhealthy lifestyle. They divorced in 1991.

Mid Life Crisis?

Both men later married younger women, which Matt Frei identifies as a way to rejuvenate themselves. Henry marriages teenager Catherine Howard in 1540, and Trump married Melania, who was 24 years his junior, in 2005.

Campaigning, Fake News and Personal Politics

You wouldn’t think it, but Henry has also had a brush with the old fake news. The printing press was a relatively new invention in Tudor England, and Henry used it to launch and aid his break from Rome. However, he gained some bad press about the war with Scotland, with sources citing that there were mass killings of women and children. Henry fought pamphlet with pamphlet, and went around sticking signs on the inflammatory pamphlets, stating that they were fables… in other words… fake news. Joanne Paul notes that we are told to believe that only those in power hold the truth. Matt Frei argues that Trump’s use of Twitter allows him to communicate directly with the electorate. Both Henry and Trump ensured that politics became personal, and that their own image was at the forefront. Referring back to ‘Personality and Propaganda’…


Matt Frei notes that Trump is a germaphobe, and its well documented that Henry would cook up all kinds of remedies to combat diseases like the Sweating Sickness. Suzannah Lipscomb goes further, calling Henry a hypochondriac.

Women and Violence

Both men have not treated women well. For Henry, this mainly concerns his advocation of beheading his wives, including 17 year old Catherine Howard. In terms of Trump, rumours about sexual misconduct were, and are, rife. In 2015, videos filmed in 2005 of him speaking about sexually molesting women came to light, and since he has come to office, 20 women have come forward to report sexual assault. He denied all claims. Ivana, Trump’s first wife, reported that he raped her at trump tower, although she later said she did not mean rape in the literal sense. Whatever she meant, Henry and Trump’s behaviour to women is and was unacceptable.

Next in line?

From a young age, Henry and Anne Boleyn’s daughter Elizabeth learnt what it meant to grow up in an unstable political climate. Her arrest at a young age, at the hands of her sister Mary I, made her realise the dangers of ruling, as Mary suspected that Elizabeth was part of a political uprising to overthrow her. Matt Frei sees Ivanka Trump in the same way, arguing that Trump is preparing her to take over the family dynasty. She is always at his side, is his senior advisor and is her own independent businesswoman. Perhaps like their fathers, Elizabeth and Ivanka have some things in common?[1]

They may have these similarities, but will Trump have the same legacy as Henry VIII? Only time will tell.

Thanks for reading!

[1] All information taken from:

‘Henry VIII & Trump: History Repeating?’ Channel 5 Documentary:


And my own knowledge.

Published by harpalkhambay

I am an English Literature and History graduate, and wanted a space to explore topics within those fields that interest me.

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