A new book details the Russian ruler’s failed courtship of the Tudor queen, who famously remained unmarried during her nearly 45-year reign
Sophie Shorland | Author, All the Queen’s Men: Power, Ambition, and the Making of Elizabeth I
October 23, 2026 7:45 a.m.
In October 1570, Ivan the Terrible ended a letter to Elizabeth I with the explosive line “I spit on you and your palace.” Unfortunately, the Russian czar had just murdered his most capable foreign ministers in a purge, meaning there was no one left who might have been able to restrain his language somewhat.
Although badly rendered from the Russian and perhaps more equivalent to “awesome,” as in inspiring awe, Ivan’s epithet of “Terrible” was justly earned: He was mercurial, fond of torture and ever ready to scapegoat someone else for his own poor decisions. The only contemporary portrait of him is highly iconographic, showing a balding, slightly wrinkled and heavily bearded man with eyes like a sad beagle. A later English visitor wrote that “he was a goodly man of presence, well favored, of a high forehead and shrill voice, a right Scythian, full of ready wit and wisdom, cruel and merciless.”
Nonetheless, Ivan was a canny politician who ruthlessly held Russia’s vast lands together. When the czar wrote his letter to Elizabeth, he was bloodily consolidating power at home while riding high in a war against Sweden. He was appalled that England’s “Virgin Queen” had not succumbed to his far-off charms.
Elizabeth, on the other hand, had an attractive voice and a graceful step. Despite a hot temper, the Tudor monarch was well aware that she needed her people’s approval to enact power. By 1570, she had also been reigning alone for 12 years and—much to the despair of her councilors and Parliament—saw little need for a husband, having successfully survived the difficult early years of her reign without one. To the amazement of much of Europe, this woman’s relatively small, wealthy island had not been invaded by a larger power, even though she remained shockingly single.
Remaining unmarried had, in fact, proved to be an advantage: Whenever one hostile actor loomed particularly large, threatening invasion or a trade embargo, Elizabeth would suddenly enter marriage negotiations with a close relative, claiming that this time she really was serious about repairing the relationship through marriage. She would prolong these negotiations until the danger was over. Losing her single status would, therefore, have been a huge diplomatic blow, cutting out this ever-present weapon out of her arsenal.
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Elizabeth had also watched her elder sister Mary’s disastrous marriage to Philip II of Spain. It ended in little except Mary’s unpopularity and the loss of Calais, England’s last remaining territory on the French mainland. Elizabeth would often cite Mary’s misfortunes to explain why she avoided marriage, forever remaining the Virgin Queen.
But what was a sensitive, paranoid despot to do when the queen of England refused to take his offer of marriage seriously, claiming not to understand his allusions to a closer alliance? For that was why Ivan had threatened to spit on the monarch: Although he hadn’t sent a letter baldly stating so to Elizabeth, he had alluded to a relationship cemented by family—presumably the precursor to proper marriage negotiations.
In 1555, Ivan had granted the English Muscovy Company exclusive rights to Anglo-Russian trade. A joint-stock enterprise operating under royal charter, the Muscovy Company also enjoyed a virtual monopoly on all European trade with Russia. In his rage, however, Ivan reneged on this arrangement, allowing other nations’ ships into his kingdom.
Irksome competition from foreign rivals threatened to disrupt England’s import of Russian goods, including rope needed for the Royal Navy’s fleet of ships. Tensions between the two countries also undermined English explorers’ aspirations of discovering a northeast passage through Russia to India and China. This route would have created unparalleled trade opportunities, providing a new market for the sale of English wool and important spices, silks and cottons. Muscovy Company merchants carried hopeful letters addressed from their queen to the Wanli emperor of China, just in case they found a way through.
Luckily for both Elizabeth and her merchants’ profits, international affairs soon intervened. In 1571, Devlet I Giray, the astute and elegantly barbered Crimean khan, head of a successor state to the Mongol Empire, decided to finally exact revenge on Moscow after two decades of on-and-off fighting in the Eurasian steppe. The Russian advance guard was overwhelmed just south of Moscow, and Ivan’s resolve wavered. Fleeing from the conflict, he filled as many chests as he could with treasure before readying for an escape up the Dvina River toward the White Sea, on the northwest coast of Russia. From there, he could hop on a ship and sail to England.
Of course, Ivan’s abandonment of his capital did nothing to help Russian morale. Giray’s armies set fire to Moscow, killing upwards of 10,000 people and enslaving many more. The city was “nothing but whirlwinds and such noise a[s] though the heavens should have fallen,” according to one contemporary chronicler. Moscow’s church bells rang until they cracked and melted, tumbling from their towers.
Russia’s capital took many years to recover. But Ivan had experienced, in the most terrifying manner, the advantages of an English alliance. Should his enemies ever come so close again, an escape route and political asylum would be necessary. With access to the Baltic Sea controlled by Sweden, the northern route through the White Sea was alone safe in times of war.
When Anthony Jenkinson, the English ambassador to Russia, met with Ivan in March 1572, the czar was newly “gracious” toward him, granting a private audience. He alluded to a “trusty and secret message, to be declared unto the queen’s majesty herself,” according to contemporary accounts. This reference to a dispatch too delicate to be entrusted to paper supports the idea that the czar proposed to Elizabeth not just once, but twice.
After some toying back and forth, Ivan finally restored the Muscovy Company’s exclusive trading rights. England—a defensible island—was a useful backup plan should Tatar armies once again burn Moscow to the ground. He could retreat with his treasure and his closest supporters, relying on English ships to stop reprisals.
In 1574, Ivan wrote to Elizabeth again, saying, “If you wish for more amity and friendship from us, ponder upon that subject and do that business by which you may increase our amity toward you.” His words are allusive: Did “that subject” and “that business” refer to marriage?
Again, Elizabeth prevaricated, avoiding an outright “no” but nevertheless remaining certain that she did not want to become Ivan’s newest wife. At that point, she would have been his fifth: The first three had died, raising rumors of poisoning, and the czar had ferreted away his most recent wife in a convent, effectively divorcing her. The English queen also saw almost no political advantage to be gained in marrying Ivan. But there was a huge potential financial advantage to be had if Elizabeth could keep the relationship on good terms.
In 1582, Ivan—by then on his sixth or possibly seventh or even eighth wife—came up with a new idea that would need to be handled tactfully: If Elizabeth wasn’t available as a prospective partner, perhaps he could marry one of her relatives.
Accordingly, the czar sent the new English ambassador to Russia, Jerome Horsey, off on a perilous journey to England, with the proposal in a cheap wooden vodka bottle “to hang under” his horse’s mane, the envoy later recalled. Equipped with 400 Hungarian gold ducats “sewed in my boots and quilted in some of my worst garments,” Horsey rode through hostile-to-Russia Lithuania, where within three hours he was arrested as a spy. Luckily, he managed to convince his captors that he was fleeing Russia as fast as his horse would go.
Arrested once again in Livonia (in present-day Estonia and Latvia), Horsey was kept in a dungeon full of snakes. He slept with the little bottle of vodka under his “best” pillow at night, raising the question of precisely how many pillows he was traveling with. Finally arriving safe on English shores, Horsey took the letters out of their vodka disguise, trying to air and sweeten them on the way to court. (They still stank when Elizabeth received them.)
Learning of Elizabeth’s distant cousin Mary Hastings, daughter of the Second Earl of Huntingdon and of distantly Plantagenet blood (descended from Edward III), Ivan sent an ambassador, Fyodor Pisemsky, to court her on his behalf. Pisemsky was tasked with providing an account of Mary’s attractions: Specifically, he was to report back on her skin and whether she was tall.
The embassy was awkward for Elizabeth. She had no desire to marry her cousin to an already-married despot, but she had also experienced how quickly and deeply Ivan could be offended. So she claimed that a plague had broken up the English court and stopped her from receiving foreign visitors. The outbreak was almost certainly fictitious, a delaying tactic to manage Russian expectations.
When they finally met, Pisemsky traveling in Elizabeth’s “very own coach in which she usually rides herself,” as he later wrote, the queen’s purpose seemed to be to flatter and blind him with spectacle rather than to open negotiations. After Pisemsky finally managed to utter Ivan’s proposals, Elizabeth expressed her apparently sincere regret that Ivan would be disappointed in Mary, saying, “I am ashamed to have her face painted and sent to your lord because she is far from beautiful.”
It was all dreadfully embarrassing for poor Mary. Pisemsky’s way of suggesting the suit was unfortunate; he declared that Ivan’s love was “straight and hard,” which in Russian was sincere emotion rather than a statement ripe for innuendo. At their first meeting, in a luxuriously decorated tent specially constructed on the northwest bank of the River Thames, Pisemsky fell on the floor to prostrate himself in the Russian manner—another cause for English sniggers. Mary became known among English courtiers as the “Empress of Muscovia,” or “Lady Mary Huntingdonska.”
Pisemsky’s unusual embassy was possibly the inspiration behind a scene in William Shakespeare’s Love’s Labor’s Lost, in which the men dress in Russian clothing to court the princess of France and her ladies in disguise. Shakespeare, speaking through the acerbic Lady Rosaline, is rather scathing about Russian court dress and manners: The men are “disguised like Muscovites in shapeless gear,” with “their rough carriage so ridiculous.” Interestingly, although Love’s Labor’s Lost is a comedy, it does not end in marriage; instead, the weddings are put off for a year, possibly a laughing reference to Elizabeth’s constant refrain of “not today” when it came to her suitors.
Eventually, Ivan was persuaded to put the idea of marrying Mary on ice, but he continued to flirt with the idea of an English bride for the rest of his life, threatening to carry his treasure over to Elizabeth’s court himself and scope out potential victims.
Luckily for all unmarried Englishwomen of the time, Ivan died in 1584, before he could put this plan into effect. He was buried in Moscow’s Cathedral of the Archangel, “where his memory [was] still dreadful,” in Horsey’s words, with his former subjects crossing themselves as they passed to protect against his resurrection.
Excerpted from All the Queen’s Men: Power, Ambition and the Making of Elizabeth I by Sophie Shorland. Published by Pegasus Books. Copyright © 2026 by Sophie Shorland. All rights reserved.
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Source: Smithsonian Magazine · Sophie Shorland
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