By any measure, David Medina is an impressive Washington, D.C., politico.

The openly gay co-founder and COO of Results for America, a data and policy non-profit, served as First Lady Michelle Obama’s deputy chief. He has also been the Democratic National Committee’s policy director and former Senator John Edwards’ presidential campaign national political director.

But even as his career progressed in the highest echelons of Washington, Medina grew preoccupied with another critical question of equality: the sexual orientation of one of the world’s greatest writers, William Shakespeare, or, more to the point, the historical record that denied the Bard’s sexuality.

After reading a reference to Shakespeare’s relationship with Henry Wriothesley, 3rd Earl of Southampton, Medina undertook a 20-year research project to uncover and understand the playwright’s sexual identity.

The result is Shakespeare’s Greatest Love, published by Disruption Books in May 2025.

LGBTQ Nation chatted with Medina via Zoom from his home in McLean, VA–where he lives with his husband, Tim DeMaristris, and their dog, Puck–about Shakespeare’s love life, Wriothesley, and what the poet would have thought of the MAGA drama engulfing the nation’s capital.

LGBTQ Nation: Tell me a little about your life today in McLean, VA, with Tim and Puck. What is life like there in the era of MAGA? 

David Medina: My husband, Tim, and I have been together for 17 years. Given the focus of my book, Shakespeare’s Greatest Love, it probably won’t surprise you that we were married on stage at the Arena Stage theater in Washington, D.C., in 2012, or named our dog Puck after one of Shakespeare’s most famous characters. 

Although we have both supported elected officials and public policies that promote equal rights throughout our decades in our nation’s capital, we’ve significantly increased our support for them this year and will continue to do so for as long as it takes—we will not let our community be ignored or erased. 

How is that advocacy related to “Shakespeare’s Greatest Love”? This book was a labor of love, maybe even an obsession.

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I read Shakespeare in college and saw some of his plays in DC. In Stephen Greenblatt’s Will in the World: How Shakespeare Became Shakespeare [published in 2004], I read that Shakespeare may have written at least some of his sonnets for and about a young male aristocrat. Then I read a second biography and found more evidence of their relationship.

This investigation went on for weeks, then months, then years. So whenever I had time, after work and on weekends, even during trips to Provincetown and South Beach, I read everything I could about Shakespeare. After 20-plus years of research, I’ve concluded that Henry Wriothesley, 3rd Earl of Southampton, was William Shakespeare’s greatest love and significantly impacted his life, literature, and legacy.

Seeing how Shakespeare’s biographies had historically ignored and minimized his personal and professional relationship with Southampton made me very angry. Still, it also made me very determined to share their love story. 

My book presents the evidence that Shakespeare wrote his first two published narrative poems, Venus and Adonis and The Rape of Lucrece, his 154 sonnets and two of his plays, The Merchant of Venice and All’s Well That Ends Well, for and about Southampton.

My apologies for putting this in modern terms, but I can’t help myself: Was he Shakespeare’s sugar baby?

Here are some facts in my book that you won’t find in other Shakespeare biographies: Shakespeare was a 27-year-old married man with three kids when he likely first met and fell in love with 17-year-old Southampton. Southampton was 19 when Shakespeare dedicated his first published work, Venus and Adonis, to him and then 20 when Shakespeare dedicated his second published work, The Rape of Lucrece, to him. 

Do you believe the relationship was consummated?

Although there is no direct evidence that Shakespeare and Southampton slept together, my book presents all the evidence that Southampton was his greatest love and had the most significant impact on his life.

Was the theater already attracting gay men in the Elizabethan era?

Engaging in homosexual acts was considered immoral by the Anglican Church and illegal by the English government during Shakespeare’s lifetime. But in Elizabethan society, boys and men of all ages, ranks, and classes ate together, slept, went to school, worked, and played together. And so English men and women lived in a “don’t ask, don’t tell” at that time.

We’ve all heard the jokes about English boys’ schools.

Same-sex bonds were socially acceptable during Shakespeare’s lifetime, and homosexual acts were very rarely punished. Theaters were places where men like Shakespeare and Southampton could be themselves publicly.

Today, gay men are often leaders of the creative class. By our standards today, it sounds like Shakespeare did a typical thing. He left his heterosexual family at home to find a creative gay crowd in the city. Do things change that much over time? 

There always have been and always will be men who are physically and emotionally attracted to other men. Shakespeare wrote about same-sex love and desire in several of his poems and plays. Those texts and subtexts are often overlooked. 

There’s no writer in history whose life has been chronicled more than Shakespeare. Why did it take until your book to uncover this critical part of his life, love, and creativity? I mean, if I were a conspiracy theorist, I would say there’s been one to cover up one of our greatest writers’ sexuality for centuries.

There are three main reasons why this true, uncensored love story hasn’t been told before. Over the last 400 years, some biographers and editors incorrectly believed there was insufficient evidence to answer the question – who was Shakespeare’s greatest love?. And that’s unfortunate because it could have changed people’s lives. It could have changed my life. It could have changed your life. The evidence is there.

Some biographers and editors have believed it wasn’t essential to know who may have inspired at least some of Shakespeare’s works, which is unfortunate. 

Some historians knew that if they did explore this greatest love question, they’d have to look at the same-sex love and desire in Shakespeare’s works, and they did not want to go there. Far too many likely felt that this love story was too controversial for their PhD advisors and publishers.

Even the movies have underplayed Shakespeare’s sexuality.

David Medina at the Royal Shakespeare Company, Stratford-Upon-Avon, August 2024

The most successful movie about Shakespeare, Shakespeare in Love, is set in 1595-1596, when Shakespeare wrote Romeo and Juliet. Southampton is not mentioned in the film. Shakespeare’s greatest love in that movie is a fictional character. The producers could have just as easily looked to the existing evidence and made a movie about his greatest real love, Henry Wriothesley, 3rd Earl of Southampton.

Could a movie like that be made?

One of my favorite Shakespeare quotes comes from The Merchant of Venice: “The truth will out.” Nonfiction writers are responsible for writing the truth as soon as possible and sharing the truth as broadly as possible. I would love to see the true love story I highlight in my book acknowledged and celebrated in every medium, including TV series, movies, and books. The facts about Shakespeare and Southampton should be fully embedded into the Shakespeare biographical narrative.

Of course, the “truth” can be dangerous. If it had been well known at the time, wouldn’t it have blown his cover at a time when the government and church were anti-gay?

I’m convinced that Shakespeare’s friends and associates were well aware of his sexual orientation. At the start of their relationship, William publicly dedicated his first two sexually charged poems to Southampton. His sonnets were shared among Shakespeare’s close friends before publication, so several artists and aristocrats knew their subtexts. And since Shakespeare’s dedication of his sonnets included Henry’s initials, albeit invertedly, they must have had their reasons for not being as open in public as they might be today.

The 2018 movie All is True features a lovely scene between an older Shakespeare and Henry, played by Sir Ian McKellen. What do you think of it?

All is True is a movie featuring two of my all-time favorite actors–Kenneth Branagh as Shakespeare and Sir Ian McKellen as Southampton. Although Shakespeare expresses his love for Southampton very passionately in this movie, he does so in just a single, far-too brief scene set near the end of Shakespeare’s life. My book provides the additional context necessary to fully understand their personal and professional relationship. On a related note, I was thrilled to receive a message from McKellen’s team recently letting me know he was looking forward to reading my book.

How did the relationship end up?

Shakespeare and Southampton first met in 1591, and their relationship continued until the year Shakespeare died, spanning 25 years. The most intense period of their relationship was in the first few years, from 1591 to 1594. That’s when Shakespeare wrote his first two narrative poems and many of his sonnets. For two of those first four years, Shakespeare likely lived with Henry, his new patron, since a plague outbreak had struck London at that time, and since there are no records showing him living elsewhere. A few years later, Southampton married a woman in a rushed and likely forced marriage, just as Shakespeare had a few years earlier.

From 1594 to 1613, when Shakespeare returned to Stratford-upon-Avon, Shakespeare and Southampton saw each other regularly, but on more professional rather than social/romantic terms. 

Would you say Shakespeare was a liberal?

Since he believed in freedom of expression, I would say yes, Shakespeare was a liberal. 

What would he have considered the current crackdowns on libraries, theaters, and drag shows?

Shakespeare would have incorporated what we’re all facing in his works. Truth seems crazier than fiction these days, and he would have reveled in exploring why politicians do the crazy things they do.

Gender roles were often mixed up in Elizabethan times.

The Merchant of Venice was written for and about Southampton. One of the characters in this play is a woman named Portia, who dresses in drag. She pretends to be a lawyer and ultimately saves Antonio, the title character, from being killed for failing to repay a loan. That play is one of nine Shakespeare plays that feature men cross-dressing as women or women cross-dressing as men.

When I was growing up, the women in my family–aunt, grandmother, and mom–were die-hard Shakespeare fans. We’d sit around the dinner table, and there would be dramatic outbursts of a Shakespeare quote that applied to whatever we discussed.

No legacy is so rich as honesty, they would practically shout. The fault, dear Brutus, is not in our stars, but in ourselves, or “There is nothing good or bad, but thinking makes it so, a line from Hamlet, and so on.

When I came out in college, my grandmother took me aside and gave me a copy of Shakespeare’s sonnets and said, I think my favorite writer might have been gay too. That meant the world to me.

My mom, on the other hand, was less accepting. And when I told her Shakespeare was probably gay, and pointed to the sonnets, she said that was just some new-fangled interpretation of Shakespeare. Who was right, my mom or my grandmother? And why are people so invested in denying the identities of long-dead figures?

Your grandmother was right. The Shakespeare-Southampton love story hasn’t been the focus because too many feel threatened by people from different backgrounds and beliefs. We’re seeing the most extreme version of this fear and hate in my lifetime, in our lifetimes right now. This is why this is the perfect time to identify and celebrate, once and for all, the greatest love of the most romantic writer in the English language. 

I’m going to quote your beautiful last line, Love always wins. Do you think love will win today, like Shakespeare won love with Henry? How can it win today when there are so many threats to it, especially against trans people? It seems impossible.

I am a proud member of the LGBTQ+ community, and I believe that an attack against one of us is an attack against all of us. I’m also an optimist. And despite all the significant, unprecedented attacks we’re facing now, I believe in the community’s strength and resilience. Two facts in particular give me hope. First, more than 9% of Americans self-identified as community members this year. That’s up from 3.5% in 2012, so more people are joining our fight for equality and freedom of expression daily.

Second, the percentage of the LGBTQ+ vote in 2024 was 8%, which was double what it was in 2008. Those attacking us will not win. We will win.

Love will win.

Chris Bull is editorial director of Q.Digital, which publishes LGBTQ Nation, Queerty, GayCities, Outsports, and INTO

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