When Sir Jonathan Bate, the Shakespeare scholar, was first shown the portrait, he gasped. In a quiet corner of the Athenaeum club off Pall Mall, art historians Elizabeth Goldring and Emma Rutherford had revealed a newly discovered miniature from the 16th century — an intricate image of a young, strikingly androgynous man.
The sitter is believed to be Henry Wriothesley, the third Earl of Southampton, Shakespeare’s first patron.
The painting, never before seen in public, has provoked two irresistible, if ultimately imponderable, questions. Was it immortalised in a sonnet? And could it hint at a tempestuous romantic relationship between England’s most celebrated playwright and the aristocrat who served as his earliest benefactor?
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In the miniature, the discovery of which was first revealed in the Times Literary Supplement, Southampton’s long hair falls in honeyed ringlets; his eyes are blue; his skin is fair. A pearl hangs from his left ear, now blackened by centuries of oxidation.
“I’ve seen other images of Southampton, but none as gorgeous or as androgynous as this,” said Bate. Rutherford agreed that the depiction was extraordinary: it is the first miniature from the period where she struggled initially to tell if it showed a man or a woman.
Everything about it — including the sitter’s pose, his hair clutched to his chest, and the informal “night jacket” he is wearing — suggests that, even by the standards of Elizabethan miniature art, it was an intimate, even an erotic image. “I think must have been for a very, very close friend or lover,” Goldring said.
The back of the portrait’s frame is covered in a decorative floral print
However, it was only when Rutherford and Goldring saw the portrait removed from its frame that its secrets were revealed.
Like other miniatures of the period, it was painted on a piece of vellum, which was then mounted on the back of a playing card, in this case from the suit of hearts. But the heart on the back has been blotted out in ink and replaced with a new outline, that of a spade — or perhaps a spear, an emblem that features on Shakespeare’s coat of arms.
The rear of the miniature is similar to the spear on the Shakespeare’s coat of arms, below
“I just couldn’t quite believe what I was seeing,” said Rutherford. “I’ve seen hundreds of 16th century miniatures; they are intensely private images. This just felt like something even more private than the face seen on the other side. We had never seen a playing card reverse vandalised like this — with the obliteration of a heart.
“And to get to the back of a miniature in Elizabethan England, you would have to have prised it out of a very, very expensive locket. This feels like a really passionate act.”
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Goldring added: “It is difficult to escape the conclusion that this was done by someone who thought they’d had their heart broken.”
Scholars will not be able to resist speculating. Could this portrait have been a gift from Southampton to Shakespeare? Might it have been returned, the heart erased, when Southampton married in 1598?
Scholars have long speculated as to whether Shakespeare, painted here in 1598, was in a romantic relationship with Henry Wriothesley
ALFREDO DAGLI ORTI/THE ART ARCHIVE/CORBIS
The miniature, attributed to Nicholas Hilliard, dates from the 1590s — precisely the years in which Shakespeare dedicated his early narrative poems, Venus and Adonis (1593) and The Rape of Lucrece (1594), to Southampton, who is also widely believed to be the “Fair Youth”, the central figure addressed in the sonnets.
There are two main strands of evidence that suggest the picture is of Southampton. Until it was recently sold to an unnamed party, it was held by a branch of his family. It resembles other portraits of him, and no other man of the time cultivated as androgynous an image.
Shakespeare’s dedications to him may suggest intimacy beyond mere patronage. The first, to Venus and Adonis, is conventionally deferential; the second, The Rape of Lucrece, is ardent: “The love I dedicate to your Lordship is without end … What I have done is yours; what I have to do is yours.”
It is tempting, Bate said, to wonder whether Shakespeare knew this miniature well. It is even possible, he added, that the poet alluded to it in Sonnet 20.
In that poem, the playwright addresses “the master-mistress of my passion”, a young man “with a woman’s face with nature’s own hand painted”.
More broadly the painting, which had been kept in a cardboard box by its previous owners, provides a new window into the 16th century. Boys played female roles on stage. In Shakespeare’s plays, cross-dressing abounds: Viola in Twelfth Night, Rosalind in As You Like It, Portia in The Merchant of Venice.
Shakespeare created a world where gender was fluid, even as Christian morality condemned sexual transgression, says Bate. “What’s so intriguing is that just looking at the detail in the miniature, and seeing that this man, this very elite figure with a bracelet and earring, these long locks of hair — you know, it really does show that Elizabethan society was very, very open about these things”.
William Shakespeare, centre, is believed to have written about men in ‘sexually passionate terms’
JOHN FAED
The debate about Shakespeare’s sexual preferences has been rolling for hundreds of years.
“Without doubt, in the sonnets we hear a man speaking in sexually passionate terms to another man,” Rutherford said. In some editions, pronouns were changed to have Shakespeare, the writer, speaking to a woman. “There have been attempts at disguise. But I think, in 2025, we’re much more open to the idea that Shakespeare was potentially bisexual.”
So was the portrait a love token, gifted to the poet and then returned to Southampton, the heart on the back eradicated? According to Bate, it is not implausible.
“I have a very strong hunch that they definitely knew each other in person. I would be genuinely surprised if that was not the case,” he said. “Whether there was a physical relationship between them is a complete unknown.”