For centuries those who questioned William Shakespeare’s sexuality were silenced by two simple facts: he married Anne Hathaway and fathered three children with her. Case closed, right? It is only in recent years–with the decline of the heterosexual presumption–that a far more nuanced answer has emerged.
David Medina doesn’t put a label on Shakespeare’s sexuality. Instead, he sets out to prove that the love of the Bard’s life was a man named, Henry Wriothesely, 3rd Earl of Southampton. Most of the information here isn’t new, but Mr. Medina skillfully puts this puzzle’s pieces together. Much of this short book reads more like legal brief than a biography, but Mr. Medina argues his case brilliantly. He also weaves a tale that is a genuine page-turner. There are surprises and twists worthy of a good melodrama–Southampton even spent time in The Tower of London.
There are no “smoking guns” here–no newly discovered love letters or other definitive evidence. There is, of course, a good reason for this. In Shakespeare’s time, homosexual acts were punishable by death. Although this law was only rarely enforced in the Elizabethan era, homophobic gossip could ruin careers and reputations. And Mr. Medina demonstrates that Shakespeare was extremely concerned with his own reputation–both before and after and after his death. But, as Mr. Medina brilliantly illustrates, the Bard did express his love for Southampton repeatedly in his sonnets, his dedications and his plays. Sometimes these expressions were coded, but other times they were out in the open–hiding in plain sight.
Southampton, it must be said, was fabulous: legendarily pretty, brilliant and precocious. He attended Oxford at twelve-years-old and was well on his way to a highly prestigious law degree when he met Shakespeare at the age of seventeen. He wore the finest clothes and sported a gold ring in his right ear, At the time of their meeting, the twenty-seven-year old Shakespeare had had several of his plays produced and was well known as an actor these plays. Southampton’s reputation also proceeded him–as a published author and heir to one of the largest landholders in England. It isn’t difficult to imagine that Shakespeare fell in love with at first sight.
So, what evidence did Shakespeare leave of his love for Southampton? The early sonnets, for starters, which he began writing shortly after meeting him. Mr. Medina makes a strong case that he was referring to Southampton when he wrote down the rhetorical question, “How shall I compare thee to a summer’s day?” Mr. Medina also references several plays with queer connections. And he takes the time to closely examine Shakespeare’s numerous dedications to Southampton. Dedications of this time were often enthusiastic but these strike this Queer Reader as excessively effusive.
The material evidence in this case is even more conclusive. Specifically, the fact that the two apparently lived together in Southampton’s mansion for a while and that this spurned homophobic gossip at the time. But the most conclusive evidence offers here isn’t new. It is an undisputed fact that Southampton gifted Shakespeare with the sum of one thousand pounds. It’s difficult to overestimate how huge a sum this was–easily millions of pounds in today’s currency. With this, Shakespeare purchased the coat of arms that had been denied to his father twenty years previously. He promptly posted it over the entrance to a huge house he purchased in Stratford. Later he would buy many more acres of land there.
David Medina does an excellent job of describing just how disreputable the performing arts were viewed in the Elizabethan era. Theatres were seen as hotbeds of vice. There’s a reason why they were kept out of London’s city limits. He also illustrates how Shakespeare’s income barely kept up with his expenses living in London with a wife and three kids to support in Stratford.
Thus, while before this gift, Shakespeare had neither wealth nor respectability, after this gift, he had both.
It should be noted that it was Southampton who commissioned the only from-life portrait of Shakespeare ever painted.
So, it’s worth asking the question, where would Shakespeare be without Southampton’s extraordinary generosity? Where would he be without the coat of arms, the legendary house–the second largest in Stratford? Without the from-life portrait? He was a great and prolific playwright and poet. But would we still refer to him by just his last name? Would tourists flock to Stratford? Would we build theaters for the sole purposely of staging his plays? Would we even know what he looked like? We can thank Shakespeare’s true love for all of these.
Needless to say, Queer Reader strongly recommends this important book.
David Medina’s Shakespeare’s Greatest Love is published by Disruption Curio.
October 9, 2025