Bad Tudor Bromances: When Powerful Friendships Went Very, Very Wrong

Bad Tudor bromances were more than just courtly drama—they were high-stakes relationships where betrayal could mean exile, disgrace, or even death. From Henry VIII’s volatile friendships to Elizabeth I’s emotionally charged alliances, the Tudor court was a minefield of loyalty, ambition, and personal power plays.

Let’s dive deep into the most infamous bromance breakups of the Tudor era—those fascinating, messy, and often fatal fallouts that reveal just how dangerous it was to get close to the crown. Whether you’re a Tudor history buff or just love a good friendship-gone-wrong story, these bad Tudor bromances deliver all the intrigue, betrayal, and backstabbing you could ask for.

Transcript of Bad Tudor Bromances: When Powerful Friendships Went Very, Very Wrong

Today, we’re going to talk about some Tudor bromance breakups. Unless you’ve been living under a rock lately, you’ll have noticed a pretty high-profile bromance breakup in the news over the past few days involving a president and a very wealthy man.

Without diving into the politics of that—because that’s beyond the scope of this channel—I thought it would be fun to take things back to Tudor England and look at some of the most high-profile bromance breakups of the period.

Let’s talk about bro breakups. Not the kind where someone unfollows you on Instagram or posts nasty things about you on Twitter, but the 16th-century kind—where betrayal might actually end with you losing your head. Literally.

The Tudor court was full of alliances, friendships, and high-stakes politics, all dressed up as loyalty. We talk about it all the time. But as we all know, in Tudor England, being close to power often meant being dangerously close to disaster. So today, in honor of a very public modern bromance implosion, we’re looking at the most dramatic, most awkward, and yes—occasionally most fatal—bromance breakups of the Tudor period.

Let’s start with the one that still makes historians wince: Henry VIII and Thomas More. The “It’s not you, it’s… well, actually, it is you” breakup.

Once upon a time, Henry VIII and Thomas More were the Renaissance version of intellectual besties. More was witty, cool, and principled. Henry loved having someone around who could match him in Latin puns and theological debates. He even made More Lord Chancellor after Thomas Wolsey fell from grace (more on that in a minute).

But then came Henry’s divorce—and his demand that everyone recognize him as the Supreme Head of the Church of England. More politely declined. He didn’t speak out against the king, but he also wasn’t going to sign on. Henry did not take that well.

At first, More was just frozen out. He was pushed into retirement, then imprisoned in the Tower, and finally executed in 1535. Henry was reportedly sad about it—which is a strange vibe when you’ve just had your old friend beheaded. Still, you can’t argue this wasn’t one of the most emotionally intense bro breakups of Henry’s reign. He cared. It didn’t stop him from sending More to the axe, but he cared.

Next up: Edward VI and the Duke of Somerset—Uncle Problems: Royal Edition.

When Edward VI became king at just nine years old, his uncle Edward Seymour, Duke of Somerset, stepped in as Lord Protector. For a while, Somerset basically ran the country, and young Edward seemed fine with that. He even called him “my most loving uncle.”

But then things started to shift. Somerset wasn’t great at making friends on the council. He made enemies. He made his fellow nobles furious because he had some populist beliefs that didn’t sit well with the elite. He actually favored ending land enclosures, for example—and we talk about that when we cover Kett’s Rebellion, which he basically bungled the response to.

Then his own brother tried to oust him. So Somerset had his brother executed. You know—just really awkward family dinners all around. Eventually, Edward grew frustrated. In his private journal, he noted Somerset’s downfall with all the emotion of an Excel spreadsheet:

“The Duke of Somerset had his head cut off today on Tower Hill between eight and nine in the morning.”

Of course, Edward’s diary isn’t exactly full of emotion in general. It just sort of lists the events that happened. And, to be fair, he had recently executed his other uncle. So you get the sense that Edward was ready to move on. It went from “my dear uncle” to “that guy we used to know.”

Next up: Henry VIII and Charles Brandon—Bro Code Violation: Royal Sister Edition.

This one is more fun—and less fatal, thank goodness. Charles Brandon was Henry’s childhood bestie. He was actually a little older than Henry, which made him super cool in Henry’s eyes. They trained together. Charles taught him jousting. They went hunting. They wrestled. Real testosterone-fueled bromance stuff. Henry loaded him up with titles, made him the Duke of Suffolk, and basically kept him at court as his wingman.

And then Charles went and married Henry’s sister, Mary Tudor in secret. Without asking permission. Cue the royal meltdown. Henry was furious. Marrying a royal without the king’s blessing was a massive overstep—even for someone in the inner circle. Brandon and Mary were hauled back to court, fully expecting to lose everything—or worse.

But Mary, clever as she was, talked Henry down. Brandon had to pay a massive fine, but Henry forgave him. Eventually, he was welcomed back. They stayed friends for the rest of Brandon’s life. He even carried Henry’s sword at Anne’s coronation. So while this was a classic “you married my sister behind my back” situation, it’s also one of the few Tudor bromance breakups with a genuine reconciliation. So that’s sweet. Charles Brandon: possibly the only man in Tudor England who pulled off a comeback like that after breaking the bro code and the law against Henry.

Next up: Robert Dudley and Sir Walter Raleigh — Two’s Company, Three Is a Power Struggle.

This one’s less a breakup and more a long, smoldering frenemy situation. Robert Dudley and Walter Raleigh were both Elizabeth’s favorites at different times. Dudley had been the Queen’s trusted companion for decades. He was her true love—handsome, polished, charming, and constantly speculated to be her maybe-sort-of boyfriend.

Then along comes Walter Raleigh—charismatic, poetic, swaggering. He had the gall to charm Elizabeth with his own flair: sending her gloves, planting potatoes, founding colonies—the nerve!

Dudley didn’t love the competition. There were veiled insults, political undercutting, and both men trying to one-up the other at court. While they weren’t openly hostile, there was definitely shade being thrown on the regular.

Raleigh later got into serious trouble for secretly marrying one of Elizabeth’s ladies, while Dudley stayed on the Queen’s good side until the end—even after he married her cousin. It’s like watching two alpha influencers compete for the same brand deal—just with more ruffs and fewer ring lights.

Okay, now: Thomas Cromwell and Thomas Howard, Duke of Norfolk — Enemies with Benefits (Until They Weren’t).

Cromwell and Norfolk were never exactly friends, but for a while, they needed each other. Cromwell was the ultimate self-made man, rising from a blacksmith’s son to Henry’s most powerful minister. Norfolk was old-school nobility—steeped in family pride and suspicious of Cromwell’s reformist zeal and upstart ways. But they could cooperate when it suited them—first to raise Anne Boleyn with Henry VIII, and then, when Anne needed removing, they both had their reasons to help.

Cromwell eventually pushed too far—especially with the disastrous marriage to Anne of Cleves. Norfolk saw his chance, pounced, and led the charge to bring Cromwell down. The irony, of course, is that Norfolk himself was arrested just a few years later and only escaped execution because Henry conveniently died the night before his sentence was to be carried out. Tudor Karma moves so fast.

Next up: Henry VIII and Cardinal Wolsey — The Mentor Who Couldn’t Deliver.

Wolsey was the man in Henry’s early reign. He made the Church dance, kept Europe talking, and probably poured the king’s wine at dinner. He helped build Henry’s image as a Renaissance prince—and did most of the paperwork to prove it.

But when Henry wanted his divorce from Katherine of Aragon, Wolsey couldn’t get the Pope to say yes—and Henry was not impressed. Wolsey was stripped of his power, sent away from court, and then, you know, accused of treason.

He died en route to London before he could be tried. So technically not a full execution, but let’s not pretend Henry was planning a warm welcome. It’s one of the sadder endings because Henry had leaned on Wolsey for so many years. But when the biggest favor of all went unfulfilled, it was over.

Next up: Henry VIII and Thomas Cranmer — The Bromance That Somehow Survived.

Let’s take a quick break from the drama for a rare sighting: a bromance that didn’t end in flames or on a scaffold. Thomas Cranmer, Archbishop of Canterbury, was one of Henry’s key allies during the Reformation. He helped annul Henry’s first marriage, supported his religious reforms, and quietly backed Protestant policies—even when the mood at court was turning.

At several points, Cranmer’s enemies tried to bring him down, but Henry always shielded him. He even gave Cranmer his royal ring once as a sign of protection and told Cranmer’s accusers to, you know, like—back off.

Somehow, Cranmer managed to keep Henry’s favor when so many others had failed. Maybe it was luck. Maybe it was loyalty. Or maybe Henry just liked the guy. Either way, Cranmer was one of the very few who stayed in the king’s good graces all the way to the end.

Henry even left him in a position of power for Edward VI’s reign. Of course, Cranmer’s story doesn’t end well under Mary—but that was a different monarch and a totally different vibe. So while it’s not a breakup, it’s worth including as the rare survivor in a landscape of shattered bromances. A unicorn, if you will, in the court of Henry VIII.

Finally: Elizabeth I and the Earl of Essex — When Flirting Becomes Treason. Now, Elizabeth technically wasn’t a “bro,” but she was a monarch, so we’re going to kind of put this one in the same column.

This is possibly the most dramatic Tudor bromance—or whatever we want to call this particular relationship. Robert Devereux was the Earl of Essex. He was young, handsome, reckless—and very aware of all three. Elizabeth adored him, at least at first. He was witty, daring, and just unpredictable enough to be interesting. He got titles. He got favors. He got away with a lot—until he didn’t.

He disobeyed her orders in Ireland. He burst into her bedchamber without permission—a major no-no. Even if you’re cute. Maybe especially when you’re cute. He openly criticized her decisions, surrounded himself with yes-men, and seemed to believe he understood what England needed better than the Queen herself.

Then, in 1601, he took things just a tad too far. He led a botched uprising in London, hoping to rally support and take control at court. It failed—spectacularly. He was arrested, tried, and executed. The tragedy here is that Elizabeth did actually love him. Not necessarily romantically—but he meant something to her.

Here’s where it gets even more complicated: He was Robert Dudley’s stepson. Yes, Robert Dudley—her first true love. So Essex was, in a way, her last link to Dudley. That made his betrayal cut even deeper. She never really recovered from it. It wasn’t just politics—it was personal. Very personal. So if Henry VIII’s bromance breakups were bloody and transactional, Elizabeth’s were something else entirely. Emotional. Tangled. Messy.

So, let’s recap. What have we learned today? If you’re going to be besties with a Tudor monarch, you might want to: keep your ambitions low, your opinions quieter and never ever marry their sister without asking first.

Whether it was petty jealousy, political backstabbing, or just the brutal reality of Tudor court life… these bromances weren’t built to last. But they do make great stories, don’t they?

Heather Teysko is the creator, writer, and producer of The Renaissance English History Podcast, the original Tudor history podcast, started in 2009. She's been writing about history online for over 25 years, since her first site on Colonial American history became number one in history on Yahoo in 1998. In 2019 she created Tudorcon, which is now a yearly event, in addition to writing books, and running TudorFair.com - a whimsical Tudor Merch shop.

She has been passionate about Tudor England since she first read Alison Weir's The Six Wives of Henry VIII 30 years ago, and subsequently moved to London after college to spend her time immersed in Tudor history (how exciting when she got to interview Alison for the first time!). In addition to history, she is passionate about travel, and has lived in 3 countries and 4 states (not counting her perpetual state of confusion), and her family (who help her host her YouTube channel occasionally).

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