The Parallels Between Henry VIII and Donald Trump

As I was researching my King’s Fool Mystery series, where Henry VIII’s real court jester Will Somers is the reluctant sleuth, I couldn’t help but notice some parallels with what was happening today. My series focuses on Will Somers and is told through his eyes, so there may be a little softening of the view of King Henry because Will looks upon him as a father figure, and sees more of his human side than history has done. But there was an awful lot of the same things going on in the 16th century as there is in the 21st century that is always a reminder that history tends to repeat itself in a myriad of ways.

Second Sons

Henry, like Trump, was an inheriting second son, never supposed to have been the heir. Henry’s older brother Arthur died not too long after he married Catherine of Aragon (left).

Fred Trump, Jr. died of alcoholism, pushing Donald to the forefront to inherit the father’s business. Both Henry VII and Fred Trump senior were penny-pinchers and thought the younger son wasn’t quite up to scratch, which led both children to live extravagant lives.

Both moved through life with a certain level of arrogance and privilege, without sense of respect for the little guy. The people around them were simply expected to work for their leader, and in Trump’s case, without even the promised paycheck. He thought it clever to stiff his contractors out of their due pay.

Sycophants

Both ruled with sycophants dogging them. Henry didn’t have a problem throwing these toadies under the cart after their usefulness proved wanting. Cardinal Wolsey (right) was a most important churchman who got him his divorce from Catherine of Aragon. It was important to Henry to have the Church on his side, but as it turned out, he would have to turn away from the Catholic Church to form his own state religion that would be under the king’s guidance in order to divorce Catherine and marry Anne Boleyn, pushing the Protestant movement into England. But then Anne Boleyn didn’t prove to be the wife he wanted after all, and Wolsey was arrested and soon to be executed, but died before that happened.

Thomas Cromwell, too, who was a secretary to Wolsey, proved to be a great schemer for Henry, concocted a trial of treason for Anne Boleyn so Henry could move on to wife #3 Jane Seymour. But after the disastrous arrangement for wife #4 Anne of Cleves, it was Cromwell who was executed for treason.

Roger Stone, Steve Bannon, and the shadowy Stephen Miller were the brains behind Trump, and manned the machine to tear down government standards in his first regime. Trump threw many under the bus when they under-achieved for him, and would do so again. And in the second regime, hundreds of conservative policy advisors were behind Project 2025 to utterly destroy and makeover the democracy of the United States into fascism. It won’t be long till Elon Musk gets thrown under the EV bus because his arrogance and ego are a match for Trump, and Trump can’t have anyone around him who might take the limelight away from him, just like Henry.

Marriages

Henry had a good marriage with Catherine of Aragon. His father wanted him to marry her when Arthur died, even considered marrying her himself, because he’d already spent her dowry. She was kept in limbo for years until Henry VII died and Henry decided he wanted to marry her after all, even get a papal dispensation to do so, her being his brother’s widow. It lasted 24 years until voices whispered in his ears that it was necessary to have a legitimate son as heir, not just a daughter. And so Henry — who hadn’t planned to embark on multiple marriages and become the laughing stock of Europe — did move to get the next wife.

Divorced, Beheaded, Died, Divorced, Beheaded, Survived, as the old rhyme goes to remember Henry’s wives: #1 Catherine of Aragon, #2 Anne Boleyn, #3 Jane Seymour, #4 Anne of Cleves, #5 Catherine Howard, and #6 Catherine Parr.

Trump, of course, moved through the Balkans for his wives except for taking a detour through the runway to get Marla Maples. Multiple children from different mothers. Where has Melania escaped to these days, we wonder?

Fake News and Tanking the Economy

Both Henry and Trump wanted their own image in the forefront, reminding all and sundry that they were in charge. Unless something went wrong, of course, but in that case, there was always a toady to throw under the bus.

But bad press is bad press, and even Henry countered real bad press by either blaming someone else or calling it “a fable”, or, in other words, “fake news”, just as Trump tends to do.

Henry threw the country into turmoil when he broke with the Catholic Church, and got the idea to seize Church lands and destroy monasteries, kicking out the monks and nuns. This caused an economic downturn. People all over the country depended on the monasteries for jobs, from milling their flour, to working the monastery lands, and for their retirement. Retirees or, as they were called corrodians, paid their money to monasteries for their upkeep and healthcare for the rest of their lives. But they were all turned away too when the monasteries were confiscated by the crown and either destroyed or sold to fill Henry’s personal coffers.

Trump, too, by implementing his democracy-killing policies and tariffs, threw thousands upon thousands out of work–except for those the courts are forcing him to rehire–and illegally tries to destroy those institutions empowered only by Congress and side-steps it with unConstitutional executive orders without regard to consequences or national security concerns. Trump deliberately tanked the economy by announcing he would impose tariffs on every country on the planet, then pulled back and paused it, but not before he and his minions bought short and made a killing in the market, and THEN he announced it. People’s retirements were wiped out in a single day. And the economy is still tanking into a recession and possibly even a world-wide Depression.

You think eggs are expensive now…

Violence Toward Enemies

Henry also had his run ins with enemies of the court, and he dealt with them swiftly, bending the law to his own whims. He got Cromwell to contrive charges against Anne Boleyn, and instead of just creating a reason to divorce her, Cromwell decided a permanent break was more called for; a trial of adultery (which, when married to the king is treason) and her subsequent execution. Though Cromwell had at first championed Anne for Henry to get his divorce from Catherine of Aragon, the tide had turned when Anne decided she did not like Henry’s chief minister.

Trump did the same to those rounded up by ICE. As of this writing, he still refuses a court order from no less than the Supreme Court to return a prisoner from an El Salvador concentration camp who was wrongfully captured and imprisoned, since he was not a member of a gang or a criminal in any way. He did not get due process, as indeed, no one sent there had.

Legacy

In terms of legacy, Henry goes down in history as a tyrant, a narcissist, and a corrupter. We can certainly project the same for Trump, since his legacy is fascism and the attempted destruction of our democracy. He is certainly the laughing stock of the world and has dragged the United States into futile and, well, stupid conflicts. But as with both, after they are gone, a new age will emerge. Henry’s discarded daughter Elizabeth did become one of the greatest monarchs of England’s history, and a woman too boot, ushering in the English Renaissance. Trump’s disregard for democracy, liberalism, and progressiveness will be his undoing and the legacy to come after him including the well-earned mistrust of any Republican candidate, when the people prevail once again.

Obviously, I have studied Henry VIII far more than Trump. I prefer distant history to contemporary. In researching Henry, I was able to find the humanity in the man. In a cursory look at Trump, I couldn’t find any humanity. Here’s a video that pretty much says the same thing.