Re-discovered portrait may depict ‘Shakespeare's secret male lover’

A lost miniature portrait, which until now has never been seen by the public, is thought to depict William Shakespeare’s secret gay lover and the subject of his erotic sonnets. The 16th-Century painting is believed to depict Henry Wriothesley, the third Earl of Southampton and Shakespeare’s first patron, whom historians hypothesise was likely the writer’s lover.

The Stratford-upon-Avon born Bard has long been rumoured to have had male lovers and is often discussed as being bisexual when the topic of sexuality is raised due to his play’s plentiful homoerotic metaphors, gender fluidity, and his poems which address male subjects; ‘Fair Lord’ or ‘Fair Youth’. The miniature which dates from the 1590s lines up on Shakespeare's timeline around the same period in which the writer 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 aforementioned ‘Fair Youth’.

A 2.25-inch portrait of Henry Wriothesley, the third Earl of Southampton, by Nicholas Hilliard. The rear of the portrait depicts a playing card heart painted over with a black arrow or spear.

University of Warwick Art Historian, Dr Elizabeth Goldring (in an article published by The Telegraph) suggested that the portrait was similar to those usually “worn on the body close to the heart and were frequently exchanged as love tokens”.

The painting by Nicholas Hilliard – which shows Wriothesley’s long hair in golden ringlets, his blue eyes, fair skin, and a pearl hanging from his left ear, now blackened by centuries of oxidation – was formerly held as part of a private collection before being purchased by an unnamed party.

Describing the painting, after seeing it for the first time, Sir Jonathan Bate, a Shakespeare scholar, said: “I’ve seen other images of Southampton, but none as gorgeous or as androgynous as this.”

Bate, was first shown the portrait, in a quiet corner of the Athenaeum club, by Elizabeth Goldring along with fellow art historian, Emma Rutherford.

Rutherford agreed that depiction was unique, and explained that it was the first miniature from the period where it was unclear initially the gender of the subject. She added that the sitter’s pose, his hair clutched to his chest and the informal ‘night jacket’ worn all suggest an intimacy and potential erotic nature to the image.

Goldring also agreed, saying she thought the artwork "must have been for a very, very close friend or lover.”

The back of the portrait’s frame is covered in a decorative floral print, however, when the frame is removed more of its secrets are revealed. Like most miniatures of the period, it was painted on a piece of vellum, before being mounted on the back of a playing card. The red heart marking the card’s suit has been defaced with a black arrow pointing up painted over it, perhaps mimicking the spear found on Shakespeare’s coat of arts.

Rutherford and Goldring both believe that the additional painting found on the back of the portrait could tell a story of heartbreak between Shakespeare and Southampton.  

Goldring said: “It’s really extraordinary, and I’ve never come across anything like it before.

“Common sense would suggest that the defacing probably occurred relatively early in its history – it’s such a visceral, violent reaction that it seems someone only with a connection to the subject would have done it.

“It is difficult to escape the conclusion that this was done by someone who thought they’d had their heart broken.”

Rutherford added: “I just couldn’t quite believe what I was seeing. 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.”

While these notions are all speculation they do raise further questions; was this portrait gifted by Wriothesley to Shakespeare? What was the cause of the defacing? Was the miniature returned and the heart painted over when the third Earl of Southampton married Elizabeth Wriothesley, Countess of Southampton in 1598?

“Without doubt, in the sonnets we hear a man speaking in sexually passionate terms to another man,” Rutherford concluded. In some editions, pronouns were changed so that Shakespeare, the writer, is speaking instead 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.”