When they hanged him, he was grateful.

So ends the sorry tale of Captain Thomas Lee (1551-1601), who lamented at the end of his trial for high treason that, according to the court record, “he had lived in misery, and cared not to live, his enemies were so many and so great.”

Lee had been offered the chance of pleading for mercy before Queen Elizabeth, but he had refused it. Better to die on the scaffold soon rather than live much longer.

In any case, the evidence against him was incontrovertible. The jury had been told that at 5pm on February 12, the accused had gone to the house of Sir Robert Crosse and proposed that they recruit “half a dozen resolute men” to go with them to “the royal palace of our sovereign lady . . . and then and there to lay violent hands on her sacred person, and to take her prisoner.”

The ruffians would bar the door from the inside, Crosse had testified, while Lee would “step unto the queen, and kneel before her, and never rise till she had signed a warrant” to release Lee’s dear but disgraced comrade-in-arms, the Earl of Essex, recently imprisoned for his attempted rebellion. If she refused, Lee had intimated that he would kill her.

Upon hearing the details of this mad plan, Crosse said he’d “sleep upon it” but instead ran straight to the authorities. Lee had by then vanished, only to be spotted by an official named William Poynes between 8 and 9pm lurking outside the door of the queen’s privy chamber at Westminster Palace.

Poynes said that Lee had been ghoulishly pale, “his countenance stern, and his face [had] great drops of sweat standing on it.” His suspicions were further aroused when Lee “lean’d hard upon him” and demanded to know whether the queen had already departed for supper.

The captain was soon apprehended and, in what must be some kind of record, tried the very next day, with the formidable attorney general, Sir Edward Coke, prosecuting. Still, Lee mounted a stout defense, pleading Not Guilty and pointing out that he had not carried a dagger, so murdering the queen could not have been his intention.

It did him no good. Sir Edward retorted that forcing a sovereign to do anything against his or her will was ipso facto treason, whether or not the accused was armed. And with that, the gentlemen of the jury “quickly found him Guilty.”

Before he was taken away, Lee insisted that the court know one thing: That while he was guilty of many other sins, and was admittedly “a bloody man and cruel,” he had never dreamt of assassinating Queen Elizabeth. His fault lay in being “loose and lavish of my tongue” when he had talked to Crosse.

All he had ever done, Lee said, was to serve her interests loyally during the ongoing colonization of Ireland and to “do the worst against her majesty’s enemies,” in the execution of which task he had “lost a great deal of blood.” In fact, the only reason he had even come to London was to beg the queen to keep employing him “in some service [in Ireland], wherein he might have some throats cut.”

The following day (February 14) he was drawn to Tyburn, where he accepted his fate in a “very Christianly” manner while “confessing his other vices, but still denying” the treason of wishing to harm Elizabeth.

**A page from the transcript of Lee’s trial**

It was a dignified end to an unedifying man, but the case of Captain Lee is nevertheless an intriguing one, not so much for the legal details of his trial, but for its depiction of a man patriotically embarking on an imperialist mission and his subsequent descent into barbarity and madness.

Lee strikes me as a real-life Kurtz, the troubled slaver and ivory-trader of Joseph Conrad’s Heart of Darkness. In 1979, Francis Ford Coppola transported him from the 19th-century Africa to late 20th-century Asia, where he was played by Marlon Brando in Apocalypse Now. Like his Conradian predecessor, Brando’s Colonel Kurtz began with every intention to carry out his orders but who eventually succumbed to the horrors of the darkness.

In Lee’s case, the Elizabethan colonization of Ireland was both his Congo and his Cambodia.

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Thomas Lee began life the son of a small Buckinghamshire landowner, who died when he was eight. Lee did not live in poverty, yet he was poor—at least compared to his rich cousin, Sir Henry Lee, and his still richer second cousin, Walter Devereux, first Earl of Essex.

In the 1570s, Essex was struggling to colonize northern Ireland, and Lee, in his early twenties, shipped out to partake in the “Enterprise of Ulster.” This expedition was one of the great Elizabethan schemes to settle Ireland by English Protestants lured by the prospect of giant land grants.

Lee would have sold whatever he had to scrape enough together to purchase the specially bred warhorse, metal breastplate, vambrace (armor for the forearm), helmet, pistol, heavy sword, light lance, and dagger required for mounted duty. As a gentleman, Lee naturally started as a captain in charge of some 25 troopers.

It was a rough business. Rebellions and uprisings mounted by the native Catholic chieftains were constant, and so too was the razing of castles and towns. It was a place where no quarter was given and the garrisons of captured outposts were hanged, they said, from trees in pairs, facing each other, so that brothers in arms were brothers in death.

There was no chivalry in Ireland. Attracted by the prospect of gaining glory by feat of arms against worthy foes, upper-class knights gravitated to the Netherlands or Portugal to earn their spurs in battle. In contrast, less socially elevated adventurers like Lee were relegated to Irish service because the fighting consisted of chasing barbarians “in hidden places as bogs, glens, and woods,” the kind of terrain where the locals liked to skulk and lay ambushes.

It was a style of combat counted as dishonorable and deceitful by the likes of Lord Grey, who sniffily complained that it “might better fit mastiffs than brave gentlemen that desire to win favour.”

Still, while the work of “pacification” was dangerous and ungentlemanly, an ambitious volunteer like Thomas Lee could leave behind the scantling acres of whatever he’d inherited from his father and potentially elevate himself to the lordship of a fiefdom. To these sort, Ireland was their oyster and the sword the best tool to open it.

Captain Lee had many admirers among the English establishment in Ulster. Archbishop Loftus reported home, for instance, that Lee’s band had “done more good service than any one captain in this land” in quelling the rebellions of the Earl of Desmond and Viscount Baltinglas.

But he also soon gained a reputation for a wild streak. There were even rumors that he had fatally poisoned Essex in 1576. The earl died of dysentery, but the fact that young Lee was bruited as an assassin is telling. Then, while back in England in 1580 he was charged with highway robbery, but was bailed out of jail by his friends. Upon his return to Ireland, he made an enemy of the immensely powerful Thomas Butler, Earl of Ormond, when he let his troops ravage his estate.

As usual, Lee enjoyed the protection of his benefactors. In Ormond’s case, the Secretary of State in Ireland Sir Geoffrey Fenton excused Lee’s behavior by remarking that he “is not without his portion of that common and secret envy which biteth most of us who serve here.” He was a poor man just making his way in the world, in other words, and Ormond ought to give him a break. In any case, he was too useful to punish.

Thanks to Fenton’s intervention, Lee was taken up by Sir Francis Walsingham, popularly known these days as Elizabeth’s spymaster, but at the time serving as her principal secretary, from which perch he wielded great influence. Through Walsingham, Lee now had a line to the queen herself—a connection that not even the likes of Ormond could tamper with.

Lee was afforded protection because he was lethally effective, yet by accumulating enemies (like Ormond) he was gambling that he could continue to stave them off while maneuvering his way to the top.

The cutthroat world of Ireland was ideal for a fellow of his talents. He soon expanded his forces to 25 horse and fifty foot, which enabled him to threaten peaceful lords and occupy their castles, which generally took the form of a three- or four-storey round tower surrounded by a lower defensive wall.

With a castle, of course, came land, possession of which was the measure for any man on the make. Unfortunately, they also came with dispossessed owners and disaffected tenants, who could be counted on to cause trouble. Gradually, as he tried to extinguish these flare-ups, Lee turned increasingly brutal in his methods, and gained a reputation for “overdoing” it a bit.

There were a few too many slaughters, a few too many blindings of inconvenient bourgeois, a few too many fatal skirmishes with English officials to ignore. In Dublin, Ormond’s allies criticized him for making the imposition of orderly government more difficult than it already was. Yet his allies, like Loftus, countered that Lee’s band had “so weeded those parts of that lewd sort of people as the inhabitants of their own report find greater quiet . . . than of many years they have had.”

Nevertheless, mounting concerns about Lee prevented him from snatching the most glittering prizes. He was kept on a strict leash. Not even knighted yet, in the mid-1580s he was still serving as a mercenary at others’ beck and call. As he complained to Walsingham after a fight in which he put Sorley Boy MacDonnell’s Scots to flight at Antrim, “I was amongst the rest as a common town dog at every hunter’s call, appointed to attend his lordship [Sir John Perrot, the Lord Deputy of Ireland], but now turned off to get my food where I may.”

Worse, Perrot and his successor (Sir William Fitzwilliam) took their time paying him and compensating him for the loss of several horses. Lee keenly felt their lack of respect, but was just as much aware that they could not survive without him doing their dirty work, especially after the outbreak of the Nine Years’ War in 1593.

That series of uprisings is too complex to go into here, but in short Lee established himself as the intermediary between the Dublin government and the Gaelic lord Hugh O’Neill, Earl of Tyrone, the leader of the coalition of clans rebelling against Tudor rule in Ulster while proclaiming their loyalty to the crown. (O’Neill was an intriguing man, in every sense of the word.)

Lee set himself up as the go-between, a position that he thought would make him kingmaker, but which in fact left him dangerously vulnerable. O’Neill, though very jolly (if murderous) and a good friend, was hardly trustworthy, and every time he broke one of Lee’s negotiated armistices it was Lee who was blamed.

Fitzwilliam, who loathed Lee (the feeling was mutual), delighted in pointing the finger and took the liberty of taking most of Lee’s lands. Lee in turn blamed Fitzwilliam’s corruption for upsetting O’Neill, who had been bribing them both, and wrote to the queen to suggest that executing Fitzwilliam would be an excellent way of forging a lasting peace with O’Neill.

All in all, not a healthy working relationship. Fitzwilliam was a relentless operator (he had overseen the execution of Mary, Queen of Scots; he had massacred the survivors of the Spanish Armada; and he had framed his predecessor, Perrot, as one of Philip II’s agents), so it’s not surprising that Lee emerged the worst from their struggle.

In 1599, abandoned by all, Lee at last again found favor, this time with the newly arrived Lord Lieutenant of Ireland, Robert, 2nd Earl of Essex, commanding some 16,000 troops. Essex was just as tempestuous, just as much of a chancer, as his distant kinsman Lee, and he appreciated the captain’s experience.

**Robert Devereux, Earl of Essex (Marcus Gheeraerts the Younger; National Portrait Gallery)**

Lee was a ruthless warrior—he always sent his superiors the severed heads of their adversaries, no fewer than seventeen on one memorable occasion (especially for the recipient, one assumes)—but, like John Paul Vann, the soldierly star of Neil Sheehan’s Vietnam-focused A Bright Shining Lie, he had seen too much and realized that victory was impossible.

He was of course willing, he said, to shed the blood of any “notorious rebel” he was ordered to, but he now considered it more effective to offer pardons to those who demonstrated their good faith.

Essex quickly discovered Lee was right after trying to come to grips with O’Neill and his fellow clan chieftains as they manoevered him into successive inconclusive skirmishes. After losing three-quarters of his men to death, disease, and desertion, Essex, with Lee mediating, proposed a parley with O’Neill. In September 1599, the two earls met alone, on horseback, at a ford in a river and discussed terms.

The truce they arranged was very simple: It would last six weeks, and was to be renewed every six weeks until the following May. If either wished to break the truce and engage in a spot of mayhem, he would be polite enough to give his counterpart a fortnight’s notice. And with that unwritten pledge in hand (so to speak), Essex and his retinue, including Lee, got the hell out of Ireland and returned home to face the music. (Lee, however, made sure to arrange the treacherous kidnapping at a parley of his old enemy, Ormond, as a goodbye present.)

Elizabeth was furious at the humiliation, telling her former favorite that if she had wished to abandon Ireland it would scarcely have been necessary to send him there. (That Essex, cheeky lad, presented himself in her bedchamber to tell her the news before she’d been bewigged and gowned, hardly improved her mood.)

Though the earl was put under house arrest in a mark of royal displeasure, Lee’s promotion of the truce with O’Neill came to be seen as wiser than it had first appeared. Among other things, it weakened O’Neill’s position among the clans and forced him to negotiate a peace with London a couple of years later.

By then it was too late for both Essex and, as we’ve seen, Lee. Essex had been released in August 1600—the queen still had a soft spot for him—but his enemies confiscated most of his offices, privileges, and monopolies (he controlled the highly profitable sweet-wine trade). Close to financial ruin, the earl stewed in resentment and envy at his London mansion, Essex House. Finally, on February 8, 1601, he launched an abortive rebellion alongside a handful of fellow grievants (though not Lee), which was quickly extinguished.

The disgraced earl was locked up to await his inevitable beheading, which neatly brings us back to the beginning—where we met a sweat-soaked Captain Lee trying to get his friend released.

**An intrusive and unnecessary plug for my own book, but just the first in a series of many, I’m afraid**

Essex’s Rebellion was a ludicrously underplanned scheme, but one of its odder facets was that the earl had not included Lee in his conspiracy, despite the captain’s presence right there in London. My own suspicion is that even Essex realized that Lee had lately gone round the bend. Indeed, there’s some evidence that Lee was so twisted up he had volunteered to assassinate Essex in a desperate effort to impress Elizabeth.

In keeping his distance from Lee, Essex was only reflecting what all the old hands were saying about him, and that was that Lee had gone full Kurtz in Ireland, especially once he’d lost Walsingham’s protection after his death in 1590.

This was a self-destructive, ruined man who had dedicated nearly three decades of his life to an anarchic, ceaseless war of treachery, murder, violence, and extortion, and in recent years several bouts of fever had exacerbated his paranoia and erraticness.

The signs had been there even from the beginning, it was now clear. There was talk (as Lord Grey put it as early as 1582) that young Thomas had led a “mis-spent life” in England and was too eager to indulge his desire for “hazard in service” abroad. Two years later, Sir Henry Wallop hinted to Walsingham that there were “many disorders in Mr. Thomas Lee.” In the early 1590s, Sir William Fitzwilliam (admittedly, no friend of Lee’s) believed Lee was “indigent and desperate” and should, as he presciently warned the government, be “barred all access to her royal sacred person.”

By the time he arrived in London, even Thomas’s cousin, the immensely well-connected courtier Sir Henry Lee, who had stood guarantor for him for so many years, had cut him off. As Sir Henry told an acquaintance, “in the course of his life this wretch hath spent me much.”

And Sir Geoffrey Fenton, once his staunchest ally in Ireland, had come to believe that Lee “had a murdering heart and a murdering hand.” Not only he, but all of Lee’s former protectors there, found the captain impulsive, mendacious, and primordially brutal. To use a dated phrase, he had “gone native” and become an “Irish savage.”

Why else would Lee have had himself portrayed as half-barbarian in a painting by Marcus Gheeraerts the Younger? Today it hangs in Tate Britain, and gives us a glimpse of how Lee saw himself in the mid-1590s.

**Captain Thomas Lee (Marcus Gheeraerts the Younger; Tate Britain)**

It is a strange painting, not helped by the fact that Lee’s not wearing trousers, which makes him look faintly ridiculous, but the point is that we see him dressed half as an Elizabethan courtier (embroidered shirt, lace cuffs, trimmed beard, a richly inlaid pistol, an embossed helmet) and half as a wild man—better known as a kerne, the lowly Irish fighter who shoelessly waded through bogs and woods. The English, of course, wore armor and rode horses—as Lee once had—which distinguished their civility from the uncivilized people they were colonizing.

In Lee’s case, disturbingly, it was as if he were proud of descending to their level, that he had half-shed his Englishness and become Irish. Indeed, one of the reasons why so many in the English establishment in Ireland loathed Lee was that he appeared to be soft on the natives and hard on his own countrymen. His friendliness with the likes of O’Neill, his support of truces with rebels, and his blaming of English immigrants for terrorizing and alienating their presumed subjects—all these longheld suspicions suddenly made sense.

Like Colonel Kurtz, he too was terminated with extreme prejudice, only it was Lee himself whose murdering heart and murdering hand did his former patrons’ work for them.

Further Reading: W. Cobbett (ed.), “The Arraignment and Judgment of Captain Thomas Lee, at the Sessions-house near Newgate, for High Treason,” in Cobbett’s Complete Collection of State Trials (London, 34 vols., 1809-28), 1, pp. 1403-1410; C. Falls, Elizabeth’s Irish Wars (London: Methuen, 1950); J.P. Myers, Jr., “‘Murdering Heart . . . Murdering Hand’: Captain Thomas Lee of Ireland, Elizabethan Assassin,” Sixteenth Century Journal, 22 (1991), 1, pp. 47-60; E. Stróbl, “The Device of the Savage Irish: The Portrait of Captain Thomas Lee,” Orpheus Noster, 9 (2017), 4, pp. 7-19.

His Murderin' Heart (and Hand)