The rediscovery of an exquisite 16th-century miniature portrait has reignited centuries-old speculation about a possible romantic entanglement between William Shakespeare and his first patron, Henry Wriothesley. Experts believe that a surprising act of vandalism of the painting holds the key to proving that this beautiful aristocrat was indeed the mysterious “fair youth” to whom the English playwright addressed some of his best loved sonnets.

Is it possible that this tiny portrait was given to Shakespeare during an illicit courtship, but now bears the scars of a doomed love affair?

When the 2.25 inch treasure was discovered by art historians Elizabeth Goldring and Emma Rutherford, both were struck by the sitter’s unusually androgynous appearance, including his long golden curls, floral patterned jacket, and inviting blue eyes. In the Elizabethan era, long hair on men was sometimes stigmatized for its feminine associations.

The work has been dated to the 1590s and is attributed to the renowned English miniaturist Nicholas Hilliard, a member of the court of Elizabeth I. Its sitter has been identified as Henry Wriothesley, 3rd Earl of Southampton, known as “Southampton,” a theory backed by the fact that it has remained in his family until very recently.

A black and white engraving depicting a bearded man in Elizabethan attire with a ruff collar, gloves, and a pendant around his neck, posed with one arm resting on a chair.



Henry Wriothesley, Earl of Southampton (c. 1610). 

Photo: Bettmann / Contributor.

Shakespeare dedicated his narrative poems Venus and Adonis (1593) and The Rape of Lucrece (1594) to Southampton. Though this was a common way of signaling appreciation for a patron, the second dedication was particularly effusive. “The love I dedicate to your Lordship is without end,” it reads. Many scholars believe that Southampton is also is the “fair youth” referred to in both.

There are other portraits of Southampton, but experts agree that this likeness is unusual for its intimate, even erotic charge, noting in particular the ringlets clutched to the man’s chest and the informality of his dress. The private image would likely have been kept in a locket and could be held and cherished in the palm of a hand.

Speaking to the Times, Goldring suggested that the painting “must have been for a very, very close friend or lover.”

What makes the portrait such a compelling bit of evidence for a potential fling, however, is not only the alluring styling of its subject, but its treatment by whoever once possessed it. When Goldring and Rutherford removed the painting from its frame, they realized that it had been subject to an act of vandalism that could easily have been carried out by a furious, spurned lover.

As is typical of miniature portraits from the period, the painting was made on a piece of vellum that was mounted onto the back of a playing card. In this case, the card was from the suit of hearts. Sometime later, however, the heart was blotted out with ink and replaced by a spade. Its pointed shape might even refer to the prominent spear that lies diagonally across the Shakespeare coat of arms.

The reverse of the miniature, showing a simple oval with a painted black arrow pointing upward on a worn, pale background.

Verso of Nicholas Hilliard, a portrait miniature of a young Gentleman, here identified as Henry Wriothesley, 3rd Earl of Southampton (1573–1624) © Elizabeth Goldring.

“We had never seen a playing card reverse vandalized like this—with the obliteration of a heart,” said Rutherford. “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.”One possible explanation is that Southampton gave the portrait to Shakespeare, who may have returned it, vandalized, when Southampton married his pregnant mistress Elizabeth Vernon in 1598.

Goldring also backs the theory. “It is difficult to escape the conclusion that this was done by someone who thought they’d had their heart broken,” she said.

The tantalizing possibility has even been raised that Shakespeare may have referred to the portrait in his Sonnet 20. In it, he addresses “the master-mistress of my passion,” who is described as a young man “with a woman’s face with nature’s own hand painted.” As exciting as it is to speculate, however, the truth of Shakespeare’s sexuality and the real nature of his relationship to Southampton will likely remain forever lost to history.