Tudor Spies: The Musician, the Magician, and the Woodcutter Who Should’ve Stayed Home

Tudor spies were not the suave, elite agents you might expect from a spy thriller—they were often chaotic, expendable, and operating far outside the rules. In the tangled world of Elizabethan intelligence, the Crown used whoever was available: wine merchants, failed actors, nervous clergymen, and occasionally, tipsy diplomats who stumbled into their roles. This messy, improvised network of Tudor spies didn’t follow a strict job description, but somehow it worked—at least for a time.

Let’s dive into the unpredictable world of Tudor espionage, from unlikely operatives like Alexander Symson to the way ordinary people found themselves swept into dangerous games of information and betrayal.

Transcript of Tudor Spies: The Musician, the Magician, and the Woodcutter Who Should’ve Stayed Home

There’s something about the Tudors that just screams secrecy. Maybe it’s all those candlelit quarters and poisoned cups, or, you know, the suspicious accidental falls from towers. Whatever it is, the Tudors were obsessed with knowing things they weren’t supposed to know and making sure that you didn’t know those things.

So when we think about spying in the Tudor world, most people jump straight to Elizabeth I and her infamous spymaster Francis Walsingham. Totally fair enough. He did create the sprawling web of informants that stretched from Antwerp to the English countryside, catching plots and decoding cipher letters like some early MI6.

But the Tudor spy game didn’t begin with Walsingham. In fact, the art of intelligence gathering had been humming along quietly since the very first Tudor took the throne. Some Tudor spies looked exactly as you’d expect — grim-faced diplomats in somber black, whispering secrets in the shadows of French courts.

Others looked a little bit less the part. They might be musicians passing through noble houses with a lute in one hand and a packet of intercepted letters in the other, or heralds, technically just messengers in fancy outfits, who somehow knew everything about everyone. Or even, as we’ll see, a bumbling woodcutter who got wildly in over his head while trying to impress a pub landlord.

This week, we’re going to go deep into the world of Tudor espionage — not just the polished spycraft of the Elizabethan golden age, but the messy, improvisational, sometimes totally chaotic world of Tudor secret-keeping. So tuck that cipher key into your doublet and let’s get started.

We are going to start before Elizabeth, before Mary, even before Henry VIII was scribbling love notes to Anne Boleyn. Our story begins with Henry VII, the king who owed his entire throne to secrecy, misdirection, and a few very well-placed informants.

The Early Tudor Spies: Roger Machado

Enter Roger Machado, not the Brazilian jiu-jitsu champion. This Roger Machado was a 15th-century herald and diplomat who somehow became one of the most intriguing and slippery early Tudor agents that we know about. He is one of those men who turns up again and again in the margins of other people’s stories — a messenger here, a negotiator there. But when you start tracing the breadcrumbs, it turns out that Roger Machado was everywhere.

Machado, whose real name was likely Roy Machado, suggesting Portuguese origins, first pops up in the 1470s as Lester Harold. We find him at royal events like the marriage of Richard, Duke of Gloucester (the future Richard III), and Anne Neville, and at the funeral of Edward IV. That tells us two things. One, he was moving in very high circles, and two, he was trusted with ceremonial work at a time when precedents and protocol were everything.

Heralds weren’t just fancy messengers. They were experts in genealogy, noble rank, and who was allowed to sit where at a royal funeral without punching someone. Machado seemed to be doing just fine until something happened around 1484.

He fled England and turned up in Portugal. Now, did he leave because of unpaid debts? Maybe. Did he have a falling out with Richard III? Also maybe. But what we do know is that by 1485, Machado was working for Thomas Grey, Marquess of Dorset who also just so happened to be Elizabeth Woodville’s son and a supporter of Henry Tudor, that same Henry Tudor who would land at Milford Haven that summer and win the Battle of Bosworth.

There’s a strong theory that Machado might have betrayed Thomas Grey to Henry, earning his trust just in time for the crown to change heads. Because after Bosworth, Henry rewarded Machado handsomely, named him Richmond Harold, and soon after sent him on diplomatic missions. And that’s where things get even more interesting.

Machado wasn’t just delivering letters. He was carrying secret instructions from the king, talking to Charles VIII of France about Maximilian’s suspicious support for Perkin Warbeck, delivering delicate messages about potential marriage alliances, and gathering information that Henry could use to keep both the Yorkist claimant and his foreign enemies in check.

We know all of this because Machado kept a journal, a rare treasure for this period. In it, we get glimpses of the tightrope walk he was doing. One mission in particular, in 1494, had him telling Charles of France that Henry VII wasn’t worried at all about Perkin Warbeck or Maximilian’s intentions. No, not at all. Totally calm. Couldn’t care less, which is a massive tell that he was, in fact, extremely worried. But that’s the job of a diplomat spy, lie persuasively, with a pleasant smile and impeccable manners.

It’s also possible that Machado was the original source of that odd little detail about Perkin Warbeck having a funny eye, something that would later be used to question his royal authenticity. Was Machado buttering up Henry by subtly insulting his rival? Or was it just an early example of Tudor spin?

As a herald, Machado wore flamboyant robes covered in royal insignia. He would have stood out like a peacock at a funeral, making him, ironically, the least discreet person to send out on a secret mission. But that’s part of what made heralds such useful tools. They could travel across borders with official status, participate in public ceremonies, and listen quietly while everyone assumed that they were just there to shout announcements and wave flags. Meanwhile, they were gathering names, overhearing gossip, and bringing it all back to the king.

In 1501, Machado was sent to negotiate with Maximilian. In 1503, he went to the Danish court. Though we’re still not sure exactly why, possibly to thank the king for not sending ships to Perkin Warbeck. His career was long and multilingual. He spoke at least five languages and it was filled with odd little gaps that suggest a lot of secret work.

He retired to Southampton, where his house was later excavated. Inside, archaeologists found imported Venetian glass and Italian ceramics, proof that Machado wasn’t traveling light. His cellar was full of valuable goods, including the very same items that he had listed in a handwritten inventory. That level of material wealth, especially for a man who was technically just a herald, suggests that spying and diplomacy had paid off for him.

He ended his life as a searcher of customs, another job that sounds super boring but probably involved catching smugglers and keeping an eye on foreign agents. In other words, still kind of spying. Was Roger Machado officially a spy? Not exactly. He was never paid with the job description of “spy.”

But Tudor record keeping is full of euphemisms: secret business, certain causes, rewards for service. And as the chronicler Philippe de Commynes once said, messenger, diplomat, and spy are all the same man. In Machado’s case, he was all three — and also maybe a little bit of a wine merchant too, but that’s a different story.

The Musical Spy: Petrus Alamire

Let’s now shift from heralds and garish robes to something a little more elegant. A man who used sheet music instead of secret codes, who could pass through courts, chapels, and great halls carrying intelligence along with motets and madrigals.

Meet Petrus Alamire. If Roger Machado was the ideal spy in a flamboyant uniform, Alamire was the spy who could walk into the heart of a rival court and be welcomed with applause. On paper, he was a scribe and music copyist. In reality, he may have been one of the most slippery double agents in the entire Tudor period.

Alamire was born Peter van den Hove. His pseudonym, Alamire, comes from the psalm and solmization syllables of the musical scale: A-la-mi-re. It was a clever musical in-joke. He was based in the Low Countries and had a hand in some of the most luxurious illuminated choir books of the early 16th century. Many of these were gifts for royalty and nobles.

One of them, in particular, a volume filled with polyphonic masterpieces, was presented to none other than Henry VIII, and it is known today as the Spy’s Choir Book. There is actually a group, Alamire, a choir in the UK led by David Skinner, that recorded the Spy’s Choir Book. About ten years ago, the first in-person interview I ever did was with David Skinner at his office at Sidney Sussex College in Cambridge. That is just a side note, but you can check out that episode too. I will link to it in the notes below.

Anyway, on the surface, the Spy’s Choir Book is exactly what it claims to be: a lavishly decorated manuscript full of courtly music created for the King’s Chapel. But historians, especially David Skinner, have long suspected that it is something else — that this gift was less about music and more about surveillance.

See, Alamire wasn’t just working for the English. He also had ties to the court of Margaret of Savoy, Regent of the Habsburg Netherlands in 1515. Around the same time he was sending that beautiful choir book to Henry, he was also allegedly feeding intelligence to Margaret about English politics, court gossip, and perhaps even Henry’s own diplomatic overtures.

The man was charming, multilingual, artistic, and perfectly positioned to overhear everything. Musicians were treated as cultural treasures, and they could cross borders without raising suspicion. They attended weddings, coronations, state dinners, and late-night entertainments. They were paid to sit quietly in the center of the room, playing their instruments and listening.

Alamire had access to people who mattered. He worked closely with Erasmus. He had connections in Mechelen and Brussels, and he maintained links to major players on both sides of the Channel. He also had a knack for flattery. The choir book that he sent to Henry was dripping in it, filled with motets praising kingship, loyalty, and divine favor. It was the Tudor equivalent of a box of custom Belgian chocolates, only handwritten and illuminated on vellum.

But the flattery didn’t work for long. By 1518, Alamire had lost favor at the English court. Letters from Henry VIII’s advisors suggest that he was suspected of treachery. Margaret of Savoy may have leaned a little too hard on him for information, and Henry decided that he could not be trusted. His diplomatic usefulness had dried up, and his music, gorgeous though it was, was not enough to keep him protected. Still, of course, the Spy’s Choir Book survives, and it is an extraordinary artifact.

Each folio is covered in rich decoration, and each page is carefully constructed not only to delight the ear, but to reflect political ideals. Many of the pieces are by composers like Josquin des Prez and Heinrich Isaac, favorites in both English and continental courts. It was as much a symbol of cultural power as it was a musical offering. In a way, Alamire is a reminder that not all spies needed to carry daggers or ciphers. Some just needed a good singing voice, a steady hand with a quill, and an ear for dangerous gossip.

The Occultist Spy: John Dee

Now, for someone who makes even the singing spy look ordinary. Because if Roger Machado was flamboyant, and Petrus Alamire was charming, John Dee was just downright strange. To call Dee a spy is complicated. He was never paid out of the secret business fund. He was not hiding under tables or intercepting letters. But the circles he moved in, and the kind of work he did for the crown, make it pretty clear that if he was not technically on the payroll as a spy, he was certainly being used like one.

John Dee was a mathematician, astronomer, astrologer, and advisor to Elizabeth I. He was also deeply involved in the occult: angelic conversations, scrying mirrors, alchemical experiments — all the greatest hits of late medieval weirdness. But it would be a mistake to dismiss him as just a fringe figure waving a crystal ball.

Dee was taken seriously. This was a time before the Enlightenment, when what we would call the occult today was considered the same as the hard sciences, when chemistry and the search for the philosopher’s stone were intermingled and regarded as one and the same. So Dee taught navigation, advised on calendar reform, and helped legitimize English imperial ambitions with hefty doses of classical learning and mystical theory.

And most crucially, for our purposes, he traveled. A lot. In the 1580s, Dee and his favorite medium, Edward Kelley, spent years moving through the courts of Central Europe. They visited Bohemia, Poland, and the Holy Roman Empire. Officially, Dee was on a personal mission, searching for patrons, conducting research, and trying to unlock divine secrets through his scrying sessions.

But unofficially, he was reporting back to England on political alliances and court personalities, on what Maximilian II and Rudolf II were whispering behind closed doors. He wrote coded letters to the court back home, and one of the signatures he used was 007. Yes, that 007. Long before Ian Fleming gave it to James Bond, John Dee was signing his confidential reports to the queen with a double zero seven, meant to signify “for your eyes only.”

He believed he had a private channel to Elizabeth and that she alone could see the information he was transmitting. Whether she ever read any of those letters is a mystery, but someone in the court certainly did, and they were happy to keep him moving through Europe, stirring the pot and reporting back.

Dee was not gathering military secrets or decoding enemy plans. He was offering a different kind of intelligence, one rooted in court politics, alchemical theory, and prophetic symbolism. It mattered in a world where rulers believed that bad omens could sway empires. Dee’s mystical knowledge gave England a psychological edge.

And it was not all smoke and mirrors. He was a serious mathematician. Like I said, he wrote about navigation, taught sailors how to chart courses across the Atlantic, and helped to shape English ideas about empire. Long before Walter Raleigh set out for war anywhere, Dee’s treatises laid the intellectual groundwork for colonial ambition. And that was the kind of influence that made him valuable.

In the 1570s and early 1580s, he advised England on a number of diplomatic matters. He even helped identify the best dates for political events using astrology. He chose Elizabeth I’s coronation date, for example. Was that intelligence? Not by modern standards, but in the Tudor court, where planetary alignment and power politics overlapped more than we usually think about, it absolutely counted.

Eventually, Dee’s fortunes waned. He returned to England and found his home library ransacked. His reputation was in shreds, and his usefulness to the crown was drying up. Elizabeth gave him the wardenship of Manchester College, mostly to keep him quiet. He died poor, obscure, and unsurprisingly still convinced that he had been working for angels the whole time.

But for a few critical decades, John Dee walked a very strange line between occult philosophy and political intelligence. Not quite a spy, but not exactly not one. He was a kind of unofficial weapon, someone you could deploy at a foreign court and trust to confuse your enemies just enough to be useful.

By the time Elizabeth took the throne in 1558, England was surrounded by enemies: Spain, France, and a continent full of Catholic powers just waiting for the right excuse to unseat the heretic queen.

Elizabeth’s government, unsurprisingly, became obsessed with loyalty. The result was the most organized, paranoid, and shockingly efficient spy network that the Tudors built. At its heart was Francis Walsingham, Elizabeth’s Secretary of State, and arguably the original spymaster. He did not invent Tudor espionage, but he did industrialize it.

He turned what had been a messy, ad hoc patchwork into a fully functional surveillance state, with agents across Europe and informants inside English households. Walsingham had the money, the backing, and, most importantly, the support of William Cecil, Elizabeth’s long-serving advisor. Together, they oversaw a shadow system of codebreakers, letter interceptors, discontented nobles turned informants, and carefully cultivated foreign contacts.

One of Walsingham’s smartest moves was recruiting Anthony Bacon and his brother Francis Bacon to run an intelligence network from abroad. Anthony Bacon gathered reports from spies in France and the Low Countries, while at home, Walsingham deployed Thomas Phelippes, the codebreaking genius who cracked cipher after cipher, often with just a little help from torture.

The most famous coup of the network came in 1586 with the Babington Plot. A group of Catholic conspirators were planning to assassinate Elizabeth and place Mary, Queen of Scots, on the throne. Walsingham let them write letters to Mary, smuggled in and out of her prison inside the hollowed-out bung of a beer barrel.

These letters were intercepted, decoded, copied, and then allowed to go forward—until Mary incriminated herself. It was a trap, and she walked right into it. That was not just good intelligence. It was entrapment, surveillance, and propaganda all rolled into one, and it worked.

Walsingham’s spy network was not only about flashy plots and queens. Much of his work was quieter. He paid off printers to monitor Catholic pamphlets. He kept tabs on foreign merchants, and he maintained contacts in places like Venice and Istanbul. Some agents were priests, some were nobles, and some were nobody at all, servants who overheard things, sailors in the right port tavern at the right moment.

And the paperwork—oh, my good grief, the paperwork. Hidden inks, ciphers, false names, fake hands. Walsingham made sure everything had plausible deniability. If something went sideways, he could always shrug and say, “Oh, that was just private correspondence.” Of course it was. And Elizabeth let him do it. She did not want to know the details. Too messy. But she understood the value. Walsingham once said, “There is less danger in fearing too much than in too little,” and that pretty much sums up the entire strategy.

When Walsingham died in 1590, he left behind a state that had grown used to constant surveillance. The machinery he built outlasted him. Robert Cecil picked it up and carried on, making sure that the eyes and ears of the crown remained open. This was about controlling the narrative and making sure that any rebellion, any whisper of dissent, was either nipped in the bud or caught just in time to be used as proof of the queen’s divine right to rule. If it meant a few forged letters or a Catholic priest rotting in the Tower, so be it. Tudor security was never subtle, but it was effective.

The Bumbling Spy: Alexander Symson

Now, not every Tudor spy was elegant, educated, or even particularly competent. Some were just available. That seems to be the only explanation for why, in 1503, a Kentish woodcutter named Alexander Symson was recruited for a secret mission involving international travel, royal pretenders, and what may have been the worst spy cover in Tudor history.

Now, I just want to give a quick note on the source for this story of Alexander Symson. In Thomas Penn’s Winter King, there is discussion of him and of his confession, more on that in a little bit. That is the main secondary source. I also found a mention of him on the Tudoriferous Podcast. So those are the only two major sources for him: Thomas Penn and that podcast. The Winter King is obviously very much based in historical fact, but there is definitely going to have to be some nuance around this as well. So I just wanted to give that quick note before we get into the story.

Symson was a sawyer, a man who sawed timber for a living. He had worked on the estate of Sir Walter Roberts for over twenty years, minding his own business and, one assumes, not getting into much trouble.

But then one day, Roberts took him aside — first during a casual walk around the grounds, and later while mucking about clearing a pond — and asked him the classic Tudor question: “Can I trust you?”

You would think that would be a red flag. But Symson, maybe flattered, maybe just confused, said, “Oh, well, yes.” And before long, he was being handed gold coins and instructions to travel to Flanders to find out what Edmund de la Pole was planning.

Let’s just pause here for a minute. Edmund de la Pole — we have done episodes on the de la Pole family, was a Yorkist exile living under Habsburg protection and quietly trying to stir up support for reclaiming the throne. England was already nervous about him. Henry VII had spies watching the ports, and here was Roberts, sending in a sawyer.

Symson actually made the journey. He got himself to Calais and then into the orbit of the Yorkist court at Sluys, lodging with a cobbler, which is where things started to fall apart. For one thing, Symson began asking a few too many questions about de la Pole’s supporters. For another, he wasn’t exactly subtle about it.

In short order, he found himself again, literally — kidnapped off the street and dragged into a back room by men loyal to the Yorkists. Honestly, you guys, this needs to be a movie. His interrogators included a friar and a man named George Neville, who had apparently graduated from the Perkin Warbeck conspiracy and was now involved with the de la Poles.

Neville threatened to cut off Symson’s ears. The friar asked questions. Symson crumbled like damp parchment. He told them everything, who had sent him, what he was supposed to find out, where he got the money, and then they let him go.

Now, why Neville and the others released him is still debated. Maybe they thought he was too clueless to be dangerous. Maybe they turned him. Or maybe they were feeding him false information and wanted it to get back to England. Either way, Symson got on a boat full of salted fish and returned home.

He didn’t go back to Walter Roberts to report, though. He quietly slipped away to Dartford, picked up some odd jobs, and might have vanished entirely into obscurity except for one small detail.

He got drunk in a pub. And in that pub, he told the landlord, Thomas Brooke, that he was planning to abduct a boy and groom him into believing he was a Yorkist heir to the throne. No big deal. He said that boy’s name was James Ormond, that he was next in line to the crown, and that if Brooke could help him secure a boat and sneak the child to France or Zeeland, there was a tidy profit in it for him. Oh, and also, could they arm themselves with a bow and a billhook in case they were pursued?

To Symson’s credit, he did try to sweeten the deal. He offered Brooke eleven marks a year for his trouble, an eye-popping salary for a Kentish innkeeper. Unfortunately, Brooke was also a cautious man. He was also aligned with George Neville, Lord Bergavenny, an enemy of Walter Roberts, so he quietly turned Symson in.

Symson was arrested and taken to the Tower. The boy, James Ormond, was found and questioned and confirmed the story. Yes, Symson had approached him, had promised him a title and land, and said he’d make him great if he followed along.

Now, whether this was all part of an elaborate double cross or just a drunken fantasy gone wildly off the rails, we will never know. Symson confessed, but his confession was vague, full of hedging, and stopped short of actually explaining why he thought abducting a child and shipping him to Burgundy was a good idea.

Some historians have speculated that this was a Yorkist plot disguised as incompetence. Others think Symson was just an easily manipulated pawn in a power struggle between Kentish lords. But one thing is clear. By the time the crown got involved, the whole thing had become a political problem. Walter Roberts, who had originally sent Symson abroad, was suddenly under suspicion.

And Sir Richard Guildford, another court insider, got tangled up too. The incident spiraled into questions of loyalty, influence, and whether Henry VII’s government could trust anyone outside its inner circle.

And for Symson, the records go quiet. We don’t know what happened to him after his Tower interrogation. He may have been released. He may have been quietly removed. Or he may have been sent back to his sawpit in Kent with strict instructions to never, ever talk in a pub again.

But his story is a reminder that the world of Tudor espionage wasn’t just Walsingham and cipher wheels. Sometimes it was a nervous woodcutter with a coin purse, a loud mouth, and absolutely no idea what he was doing.

So now it’s clear that spying in the Tudor period didn’t look like just one thing. It wasn’t only cloak-and-dagger operations in candlelit cellars or neat little men scribbling secret codes in invisible ink. It was messy, improvised, sometimes brilliant, sometimes embarrassing.

There were professionals like Walsingham and his paid informants. There were also heralds like Roger Machado, officially in gold braid, unofficially ferrying information across Europe. There were musicians like Petrus Alamire, who could slip between courts with music manuscripts that doubled as diplomatic messages. There were astrologers and alchemists like John Dee, who convinced the government to fund his travels because he might, at some point, talk to angels who had state secrets.

And then there was Alexander Symson, bless him, who walked straight into a trap, came back home, and invented a second entirely unrequested plot involving the kidnapping of a child, possibly while tipsy, possibly while being played like a fiddle. Probably both.

That’s the thing about Tudor espionage. It didn’t follow a job description. The crown used whoever was available. Sometimes they were brilliant. Sometimes they were just disasters. Sometimes they were exactly what was needed, forgettable, expendable, and just convincing enough to get someone to talk.

So if you’ve been imagining Tudor intelligence as a sleek system of loyal agents, you need to adjust that mental picture. It was more like a rickety stage production held together with scribbled notes, second sons, part-time wine traders, and people who definitely weren’t cleared for what they were hearing but heard it anyway. And somehow, for the time, it worked.