712 Shakespeare's Greatest Love (with David Medina) | New Play About Shakespeare's Collaboration with Marlowe

Summary

The History of Literature Podcast - Episode 712: Shakespeare's Greatest Love (with David Medina)
Host: Jacke Wilson
Guest: David Medina
Release Date: June 30, 2025

---

Introduction

In Episode 712 of The History of Literature Podcast, host Jacke Wilson delves into one of literature’s most intriguing questions: Who was William Shakespeare’s greatest love? Joining him is David Medina, a seasoned political analyst and author of the book "Shakespeare's Greatest Love," which explores the deep and possibly overlooked relationship between Shakespeare and Henry Risley, the 3rd Earl of Southampton.

---

Background on the Episode and Guest

David Medina brings over three decades of experience in politics and public policy to the conversation, holding senior roles in the White House, Senate, and various civil rights organizations. His academic credentials include a BA from the University of Chicago and a master’s degree from Harvard's Kennedy School of Government. Medina's transition from politics to literature showcases his lifelong passion for biographies and the personal lives of influential figures.

David Medina (17:21):
"I love your podcasts and it's just great to be with another literature enthusiast and fellow Midwesterner."

---

Shakespeare’s Love Life: An Overview

Jacke Wilson opens the discussion by highlighting Shakespeare’s enduring legacy as a writer about love, noting the complexities of his personal life—leaving behind his wife and children for London. While Shakespeare’s works teem with diverse portrayals of love, the question remains: Who was the object of his deepest affection?

Jack Wilson (01:07):
"Who did Shakespeare love? Who did he love the best? Our guest today believes the answer has been hiding in plain sight all along."

---

Introducing Henry Risley, 3rd Earl of Southampton

Medina introduces Henry Risley, a 17-year-old aristocrat, as Shakespeare’s likely greatest love. Their relationship, marked by mutual admiration and substantial patronage, is supported by textual evidence from Shakespeare’s sonnets and narrative poems.

David Medina (20:13):
"I picked up 'Will in the World' by Stephen Green and fell in love with it. But what really sparked my interest were the brief references to Henry Risley, the person to whom Shakespeare dedicated his first two published narrative poems and likely wrote his sonnets for."

---

Establishing the Connection

Medina outlines the probable meeting between Shakespeare (age 27) and Southampton (age 17) around April 1591, likely at a London theater. This encounter set the foundation for a profound personal and professional relationship.

David Medina (21:07):
"They met in around April 1591. Their relationship was strongest during the period between 1592 and 1594, coinciding with the writing of Shakespeare's sonnets and narrative poems dedicated to Southampton."

---

Southampton’s Influence on Shakespeare’s Career

Southampton’s financial support was pivotal in Shakespeare’s career, enabling him to invest in the Lord Chamberlain's Men acting company and secure a family coat of arms—actions that significantly elevated Shakespeare’s social standing and legacy.

David Medina (38:43):
"Southampton helped Shakespeare secure his King's Men's life portrait and funerary bust commissions, and even likely funded the purchase of New Place, Shakespeare’s grand residence in Stratford."

---

Literary Evidence and Scholarly Perspectives

Medina presents compelling literary connections between Southampton and Shakespeare's works, particularly "All’s Well That Ends Well" and "The Merchant of Venice." He argues that characters and themes in these plays reflect the personal dynamics between Shakespeare and Southampton.

David Medina (35:55):
"Shakespeare wrote plays for and about Southampton beyond just the sonnets, extending to narrative poems and plays like 'All’s Well That Ends Well' and 'The Merchant of Venice.'"

---

Contemporary References and Public Perception

Medina references contemporary works that allude to the relationship between Shakespeare and Southampton, such as the narrative poem "Willoughby His Avisa," which explicitly describes a triadic relationship involving Shakespeare and Southampton.

David Medina (37:53):
"In 'Willoughby His Avisa,' characters resembling Shakespeare and Southampton are depicted in a way that mirrors their relationship as described in the sonnets."

---

Challenges in Historical Recognition

The episode addresses why this significant relationship has been historically overlooked, attributing it to societal discomfort with same-sex relationships and the lack of concrete evidence like surviving letters between the two men.

David Medina (50:42):
"Some biographers chose not to address this relationship because highlighting a same-sex love would have been too controversial for their PhD advisors and publishers."

---

Impact on Shakespeare’s Legacy

Medina argues that Southampton’s patronage not only supported Shakespeare financially but also played a crucial role in preserving his legacy through commissions like the Cobb Shakespeare portrait and the funerary bust in Holy Trinity Church.

David Medina (43:27):
"Southampton’s support was instrumental in securing the resources that allowed Shakespeare to invest in his career and ensure his legacy endured."

---

Future Discoveries and Continuing Research

While Medina acknowledges the absence of direct correspondence between Shakespeare and Southampton, he remains hopeful for future discoveries that might shed more light on their relationship, drawing parallels to the well-documented relationship between Michelangelo and Tommaso di Cavalieri.

David Medina (54:03):
"If letters were to be discovered, akin to those between Michelangelo and Tommaso, it would provide invaluable insight into Shakespeare and Southampton’s relationship."

---

Conclusion

The episode concludes with Medina emphasizing the importance of understanding Shakespeare’s personal relationships to fully grasp the depth and nuance of his literary works. He urges listeners to consider how these personal dynamics influenced Shakespeare’s portrayal of love and human emotion.

David Medina (52:36):
"I do not believe that anyone can truly understand his masterpieces without understanding the man. Who was he? What was he worried about at the time? Who was he most in love with—all of these factors bleed into his works."

Jacke Wilson wraps up by promoting Medina’s book, "Shakespeare's Greatest Love," and encouraging listeners to engage with the ongoing exploration of Shakespeare’s life and loves.

---

Notable Quotes

• Jack Wilson (01:07):
  "Who did Shakespeare love? Who did he love the best?"

• David Medina (20:13):
  "Shakespeare wrote plays for and about Southampton beyond just the sonnets."

• David Medina (43:27):
  "Southampton’s support was instrumental in securing the resources that allowed Shakespeare to invest in his career and ensure his legacy endured."

• David Medina (52:36):
  "I do not believe that anyone can truly understand his masterpieces without understanding the man."

---

Further Information

For more insights into Shakespeare’s personal life and David Medina's discoveries, visit historyofliterature.com or follow the podcast on Facebook. Support the show through Patreon or donations at historyofliterature.com/donate. To join the upcoming Literature England tour in May 2026, contact Jacke Wilson at [e-mail] or visit the event page at greatestloves.com/events.

---

This summary captures the essence of Episode 712, focusing on the substantive discussions between Jacke Wilson and David Medina about Shakespeare's personal life, his relationship with Henry Risley, and the broader implications for understanding his literary works.

Transcript

[Jack Wilson]

The History of Literature Podcast is a member of the podglomerate Network and Lit Hub Radio.

[Nordstrom Ad]

Summer's here, and Nordstrom has everything you need for your best dress season ever, from beach days and weddings to weekend getaways in your everyday wardrobe. Discover stylish options under $100 from tons of your favorite brands like Mango Skims, Princess Polly and Madewell. It's easy, too, with free shipping and free returns in store order pickup and more. Shop in stores [e-mail] or download the Nordstrom app.

[Jack Wilson]

I think you're on mute.

[LinkedIn Ad]

Workday starting to sound the same.

[Jack Wilson]

I think you're on mute.

[LinkedIn Ad]

Find something that sounds better for your career on LinkedIn with LinkedIn job collections, you can browse curated collections by relevant industries and benefits like Flexpto or Hybrid Workplaces so you can find the right job for you. Get started at LinkedIn finding where you fit.

[Jack Wilson]

LinkedIn knows how hello. William Shakespeare might be the greatest writer about love who has ever lived. Certainly he's one of the most prominent, thanks to his plays and sonnets still being read and performed over 400 years later. And yet, as we know, Shakespeare left his wife and three young children in Stratford upon Avon and moved to London. Was there love in his marriage? Perhaps? Was there love elsewhere? Signs point to yes, although the biographical record, as so often is the case with Shakespeare, raises as many questions as it answers. We know what Shakespeare thought about love in all its dynamic variants, and we know the words he found to express those thoughts. But to ask a very simple question. Who did Shakespeare love? Who did he love the best? Our guest today believes the answer has been hiding in plain sight all along. We talked to David Medina about Shakespeare's greatest love and why their relationship has been overlooked for centuries. Today on the History of Literature. Okay, here we go. Welcome to the podcast. I'm Jack Wilson. Glad you're here. We're getting close, people. Getting close to giving you all the information about our very first History of Literature podcast tour. And yes, we are going to England. And yes, we will include Shakespeare among the authors whom we will be exploring together. We're starting in London itself, home of so many wonderful writers. The trip is going to be in May of 2026, but unfortunately spots are limited, so act early. If you'd like to join us, check our website, our newsletter, our show notes for more information, which will be posted very soon and I'll be talking about it here on the podcast. Or you can email me to say, hey Jack, let me know when you know more. Or yes, I'm intrigued. I would love to hear from you on this or anything really, but this especially because we are looking forward to having a small group travel with us as we travel through space and time together, meeting up with some favorite guests of the podcast who are eagerly signing up to be part of this too. We're going to be all spending some quality time together and they will be there to answer your questions and say hello and just generally help us celebrate life and literature. That's the plan. So [e-mail] that's J A C K E wilsonauthormail.com or go to historyofliterature.com and contact us that way through the contact link. If you love literature, this trip will be for you More information very soon. Or if you're listening to this on July 1st or after. It's possible that the information has already been posted. So sign up if you're interested interested so you don't miss out. Emma and I will both be there and we would love to have you join us. Moving on, there's an article from the Guardian on a new play that dramatizes the story of Christopher Marlowe and William Shakespeare working together. The play was inspired by some reports a few years back that Marlowe and Shakespeare collaborated on Shakespeare's plays Henry VI, parts 1, 2, and 3. The evidence is there in the language. This has long been rumored, but now a panel of experts was convened by Oxford University Press to really look into this question. 23 academics in five countries scrutinized the textual analysis, and they found certain unusual combinations of words that they believe were unique to Marlow in that period. And the example they give in the article is the phrase glory droopeth, glory drupeth, which is Marlovian, apparently. Glory drupeth. Imagine that. Imagine being Christopher Marlowe, the brilliant Christopher Marlo, and you have your reputation already. Your star is pretty bright. Your reputation is great. Your plays are famous. You're one of the great what ifs in literary history. We did a whole episode on this, the Great what if Christopher marlo. And then 400 years after your death, you get another credit, a little more to add to your legacy. A bit of additional posthumous fame that you were collaborating with the Goat on some of his plays. And why does this, why does this accrue to your. To your legacy? It's all because your quicksilver mind like to reach for phrases like glory droopeth. And that made you stand out. Glory droopeth? More like glory groweth, glory nearly erect the play is called Born with Teeth by Liz Duffy Adams, who imagines what it would have been like for Shakespeare and Marlowe to work together. A steamy wrestle is how the play's been described, how their relationship has been described. The two have a mutual talent crush. Sounds kind of like Lennon and McCartney, right? Two of my heroes. Two. Two artists who admire each other, who are trying to outdo each other, envious of the other's talent, but also appreciative, excited by the prospect of soaring together in the play. Marlowe is. Is a rock star experience seeker who wants to fully embrace life, including taking risks. Shakespeare's an actor who's just getting started. He's the underdog at this point in their careers. He's looking up to Marlo as the famous and more accomplished playwright, the writer of Tamburlaine and Faustus, which were two smash hits. But Shakespeare's no slouch. He's already got talent to burn too. And over the course of their working together, their status and creative energies kind of seesaw. Sounds like a very interesting play. I love stories about creativity and collaboration. Which reminds me, I've got to watch Amadeus again as soon as I finish the Heartbreak Kid, the old one with Charles Grodin, Elaine Mays film, which is also highly recommended. Okay, back to the article, because the conclusion of the article sets us up for our guest today. Here's the director talking about the play. This is the play about Shakespeare and Marlowe collaborating. In one sense, Shakespeare has become a kind of saint. We think of him as this playwright who could write any voice. The upper classes, the lower classes, the mad, the sane. So we tend to think of him as this endlessly empathetic character riding alone in his garret, imagining himself into different people's minds. What the play does is to remind us that he's also a man and he was writing at a time when collaboration was. Was der. End quote. And here's a professor of Shakespeare studies, Gabriel Egan, who was one of the scholars, the 23 I mentioned, whose computational analysis had helped convince fellow OUP colleagues to put Marlow on the title page with Shakespeare. Of these plays equal billing for authorship. The article. The article says that Egan was talking about the. The fascination that the public have with authors lives. Even though some of his academic colleagues think that biographical details are not essential to the study of literature. But that's not what the public thinks. As we see from huge sales of biographies. Egan added, people outside of academia care very much about the person who wrote the thing. I'm out of line with my profession because I also think authorship rather than really matters. End quote. People care very much about the person who wrote the thing. Yes, indeed. And with Shakespeare, we wonder just how, just how did this guy learn so much about so many things? And how did he learn so much about love? How did he. Why did he care so deeply about love with all of its. All of its exterior, back and forths? I mean, the external we see in the dialogue between lovers, the accusations, the desperate pleas, the professions of it and the profusion of it. Think of all the characters in Shakespeare plays who fall in love and how different the scenarios are and what we take from them. Romeo and Juliet are like. They're like the Adam and Eve of Shakespeare, characters in love. But the others aren't pale shadows of those two. They're different. There's Beatrice and Benedict, witty and passionate, holding each other at a distance while they spar. There's Anthony and Cleopatra. Love with empires at stake. There are the Macbeths, love in a death clinch as the two spiral into darkness and oblivion. Like Holmes and Moriarty at Reichenbach Falls. There's Othello and Desdemona, love blinded by the green eyed monster. There's the love of Ferdinand and Miranda in the Tempest, and Henry and Catherine and Henry V. And we could go on and on. There's love everywhere, love all around. Love is in the air. Shakespeare dives into the well of love again and again. And not just for the dramatic potential of will there, won't they? But for the psychological effects of love. The effects on a character's inner life and motivations. The jealousy, the rage, the frustration, the exhilaration. Shakespeare, the dramatist, loves love. And Shakespeare, the sonneteer, goes even farther. That guy writing those sonnets doesn't just love love. He needs love. He wants it. He wants at times to be rid of love, to escape its grasp, but also to tame it, to moderate it, to hold it at bay. He's like an addiction, saying, yes, this thing is powerful, it's all consuming, it will tear you apart. Maybe we should avoid it altogether. You see what it can do. But also you see what it can do. You felt it. Let's indulge ourselves a little. Just enough. Life won't be the same without it. Or let's give in and damn the consequences. It's time to go on a bender of love. Oh no. Hangover time. That was the mistake. You get the idea. Love is not just his plot. It's his poison and his pleasure palace. It's his poppy Anne hathaway has gotten a bad rap over the years as Shakespeare's wife. He did leave her a couple of. I mean, he left her in Stratford while he went to London. There were a couple of famous leavings there. I guess he left her first. He left her at home and then he left her his second best bet bed in his will. Of all the things to survive in legal documents, that's the one we hear about. I'm sympathetic to those people who actually question that one. Who or who actually can we use actually as a verb? They actually that one. They say actually the second best bed was a good thing, it wasn't just a dish. And there's a plausible scenario that Shakespeare actually had more affection for his wife than history has typically considered. I'm all ears for that. With so little evidence, there's room to fill our understanding with theories. But there's also evidence that he loved others. Certainly his life had room for others. He was alone in London in a theater company. Hello, we can all read the gossip pages today. Some things never change. So let's stop there, then let our guest David Medina fill in the gaps with what he's found. Who was Shakespeare's greatest love, and why do we hardly ever talk about it? We'll ask those questions and hear some answers after this.

[David Medina]

Foreign.

[Jack Wilson]

This is an ad by BetterHelp. Hey, it's summer, but that can come with a lot of stress, especially for those of us who work. Workplace stress is one of the top causes of declining mental health and holidays and vacations can help, but those aren't long term solutions. Sometimes talking to a professional can help you navigate the challenges of the workday or any day, so you can be the best version of yourself. BetterHelp is the world's largest online therapy platform, Having served over 5 million people around the world. You can join a session with a click of a button which allows you to fit your session into your busy life and you can switch therapists at any time. As the largest online therapy provider in the world, BetterHelp can provide access to mental health professionals with a diverse variety of expertise. So unwind from work. With BetterHelp, our listeners get 10% off their first month at betterhelp.com literature that's betterhelph e l-p.com literature with a Venmo.

[LinkedIn Ad]

Debit card, you can Venmo more than just your friends. You can use your balance in so many ways. You can Venmo everything. Need gas? You can Venmo this. How about snacks? You can Venmo that. Your favorite band's merch. You can Venmo this or their next show. You can Venmo that. Visit Venmo Me Debit to learn more.

[Jack Wilson]

You can Venmo this or you can Vemo that.

[Nordstrom Ad]

You can Venmo this or you can Vemo that.

[LinkedIn Ad]

You can Vemo the Venmo MasterCard is issued by the Bancorp bank and a pursuant to license by MasterCard International Incorporated. Card may be used everywhere MasterCard is accepted. Venmo purchase restrictions apply.

[Uber Ad]

You know that feeling when someone shows up for you just when you need it most? That's what Uber is all about. Not just a ride or dinner at your door. It's how Uber helps you show up for the moments that matter. Because showing up can turn a tough day around or make a good one even better. Whatever it is, big or small, Uber is on the way. So you can be on yours. Uber on our way.

[Jack Wilson]

Foreigning me now is David Medina, who has worn a few hats in his life. For more than 30 years, he's worked in politics in Washington, D.C. holding senior roles in the White House, Senate, national labor and civil rights organizations, and presidential campaigns. David received his BA from the University of Chicago and a master's degree from Harvard's Kennedy School of Government, and he's here today to discuss his new book, Shakespeare's Greatest Love, which tells the true, uncensored love story of William Shakespeare and Henry Risley, 3rd Earl of Southampton. David Medina, welcome to the history of literature.

[David Medina]

Thank you so much. It's great to be here. I love your podcasts and it's just great to be with another literature enthusiast and fellow Midwesterner.

[Jack Wilson]

Okay, well, some people might wonder, speaking of us personally, some people might wonder how literature played a role in your life even as you were making your way through the corridors of power in Washington, dc. Have you retired from politics and public policy and taken up literature? Or has literature been part of your life even as you've pursued your career?

[David Medina]

Yeah, I've been obsessed with biographies, mostly political biographies, my entire life. And like most fanatics, I've read, you know, many biographies several times. I love Team of Rivals, Hamilton the Power and and so literature has played an important part of my life, but I've connected it to my professional life as well.

[Jack Wilson]

Yeah, I wonder how many people you and I are around the same age. I wonder how many people were inspired by the story of Robert Moses and Robert Caro's book the Power Broker and inspired to become part of politics and public policy in some way. It was such an amazing book. And I knew a bunch of people who were reading it and then decided to become public policy majors.

[David Medina]

No, I agree. It showed you how one person could affect an entire community, an entire state, an entire country. And I just heard a podcast with Robert Caro a few months ago, and he added a lot of flavor to why he chose Robert Moses. And I didn't know that his wife had helped him prepare the book and the manuscript. And so I love hearing and reading about public officials, but I think unlike most readers, I am just as interested in their personal lives as I am accomplishments.

[Jack Wilson]

Yeah, and the scale of it. I mean, you know, to build roads and bridges and highways and parks. It's, you know, it's one thing to read about Napoleon and think he's transforming a continent or something. And it's another thing to think, well, you know, I would really love to have a pedestrian street in my neighborhood, or I would really love to have, you know, some green space here. And to think that here's somebody who's able to make that kind of change in people's lives.

[David Medina]

Yeah, no, I agree. But, you know, one of the parts of the book I enjoyed the most is when people came together in southern Manhattan and pushed against his plans to have the highway right through their neighborhoods. And so they stop him for the first time in his career so that people have the power eventually, ultimately.

[Jack Wilson]

Right, okay, so let's turn to Shakespeare. When did you start reading Shakespeare?

[David Medina]

You know, in late 2004, when my preferred presidential candidate lost and I found myself As a single 35 year old, I decided that I wasn't going to read political biographies that fall. And so I picked up Will in the World by Stephen Green, New York Times bestseller, and fell in love with it. But what really sparked my interest were the brief references in it to someone named Henry Risley, 3rd Earl, Southampton, as the person to whom Shakespeare dedicated his first two published narrative poems and the person to whom he likely wrote his sonnets for. So those few paragraphs in that book started my 20 year plus obsession with finding out what was behind the man behind the masterpieces.

[Jack Wilson]

Right, okay, so let's talk about this relationship or what we know about this relationship between Shakespeare and Henry Risley, 3rd Earl of Southampton. How old would Shakespeare have been? Where would he have been in his career? I mean, I guess he's. He's got this wife, he's got three children, he's in Stratford upon Avon. He leaves for London, he starts to make his way. He starts writing some plays, he's acting in plays. But where exactly was he in his career? What had he written and how old was he?

[David Medina]

Yeah, so Shakespeare was likely 27 years old when he first met 17 year old Henry Risley in around April 1591. And I believe that the social ambiguity of London's public theaters at this time make them the most likely venue for the first encounter between this artist and this aristocrat. Since theater goers at this time represented all ages, classes and ranks, Shakespeare had likely written five of his plays by this time. So the Taming of the Shrew, the Two Gentlemen of Verona, Henry vi, parts two and three and Titus Andronicus. And I think it was love at first sight. William, you know, according to the first biographical sketch of him by John Aubrey, you know, calls him a handsome and well shaped man. Very good company, very pleasant and smooth wit. The Cobb Shakespeare portrait, the only life portrait made Shakespeare, you know, shows him with fair skin and rosy cheeks and auburn hair and a clean shaven beard and mustache. So he, he was an attractive man who's 27 and he was quite popular. You know, he had written very popular plays and so he was rising star. You know, I think there's a lot of evidence that Southampton, even though he was only 17 at this time, was already a regular theater goer. His Italian tutor wrote a book called Second Fruits around this time, making clear that he was going to plays. Sonnet 104 confirms that Shakespeare and Southampton likely met during the month of April, since it reads three April perfumes and three hot June's burns, since first I saw you fresh, which yet are green. And there's a Cobb Southampton portrait which was painted around the time Southampton first met Shakespeare. And it shows him as an androgyn with slight build and pale skin and gray blue eyes, very effeminately beautiful. And so again, I believe they met in around April 1591. They met in a theater and they probably connected over their mutual love of the theater.

[Jack Wilson]

And what else do we know about Southampton? What kind of family connections did he have? Was he wealthy? Maybe you could sketch in for us just what it meant for someone of his background to be going to the theater. It was, I mean, we might think of it today as well. Of course, that's what a refined, elegant person who is, you know, someone of means might be doing. They'd probably learn an instrument, they'd probably have artworks and so forth and they'd go to the theater. But actually this really was, the theater was like, you know, half a step away from a brothel kind of atmosphere. And it was almost like slumming it. So what would it be like for him to be turning up at the theater? How common was that for people of his background? And just how rarefied of air did he live in when he wasn't going to the theater?

[David Medina]

Yeah, you know, again, theater going was for everybody back then. So people of all ages, classes and ranks, you know, Southampton, you know, despite his young age, he had already earned an advanced degree from a prestig. He was studying law in London. And he was also a member of one of England's most prominent and wealthy families and a strong contender to be one of the Queen's Queen Elizabeth I's future favorite. So he was very well known despite his young age. 17. It would have been common for him to go see public plays. That's what other aristocrats like him were doing at the time. He became the third Earl of Southampton right before he turned eight when his father died. And so at that young age, he was immediately taken from his mother and sole surviving sister and placed into the guardianship of William Cecil, the first Lord Burleigh, who was, you know, the most prominent person in the land other than the Queen. He served as her chief advisor. He was the chancellor of Cambridge University and master of the Court of Words. And you know, when I was writing, thinking about or writing this book, you know, I asked myself, who likely initiated the conversation? You know, I work, so I don't create any fictional conversations. But I think that Southampton likely started the conversation with Shakespeare in the theater. He was already very self confident, even though he was a very young age. He had written a couple of essays. He was royal Guardian, talking about how freedom should triumph over reason, especially for young people. I do think it was likely some version of love at first sight. The two of them, Shakespeare and Southampton, would have impressed each other on several levels when they first met. Shakespeare was handsome, witty, you know, a rising theater guy. He had very successful plays at that point. Henry vi, parts two and three. But, you know, he also, you know, worked in the theater and in a brothel filled community. And so those were probably very tiddling facts for the young Southampton to talk about.

[Jack Wilson]

Right. And we know from other sources that he is beguiling men and women. The Earl is. And he also seems to have had some issues with the Queen and king. Was he kind of a, a fighter? Was he somebody who was causing trouble and known as being sort of rebellious or contentious or what? What was his reputation? Kind of, setting aside Shakespeare, what kind of figure was he making as he was making his way through the world.

[David Medina]

Oh, yeah. You know, his contemporaries, his colleagues, those at court would have considered him pretty but proud. They would have thought of him as being independent but extravagant. All those things you just alluded to. And there were several works, contemporary works, written about him that also called into question his suspected homosexuality. So it wasn't just Shakespeare's works. The year that he and Shakespeare first met, there was a narrative poem entitled Narcissus written by Lord Burleigh's secretary that attacked Southampton as being gay and effeminate in its text and in its dedication.

[Jack Wilson]

And.

[David Medina]

And this work is largely ignored by a lot of Shakespeare biographies, as Southampton is. Is generally as well to dedications by Thomas Nash, Another famous contemporary writer referred to Southampton as Ganymede, Zeus's boy lover in one and as a dear lover of poets in another. And that reference to dear lover poets was an undeniable reference to Shakespeare since Shakespeare just dedicated his Venus and Adonis soon before Nash wrote this dedication. And so he was very well known, not thought of positively by everyone and at all times, but also not just talked about, but written about.

[Jack Wilson]

But to say that he's gay and effeminate, we should probably remind everyone or discuss this, if there's anything worth discussing, that this is an era where the female characters are routinely played by boys or young men with this kind of quality. And it would have been not something that Shakespeare would have not been accustomed to.

[David Medina]

For example, yeah, homosexual acts were considered immoral by the Anglican Church and illegal by the English government. But that didn't mean that strong bonds weren't being formed between boys and men of all ages, classes and ranks. There was also a law, and some of your other guests have mentioned it, the act for the punishment for the vice of buggery by Henry viii. But it was still common for boys and men to work together, to play together, to perform on stage together, to share beds together. So this early relationship between Shakespeare and Southampton wouldn't have necessarily seemed out of place at the time, but officially it was immoral and officially was illegal if they did engage in sexual acts together.

[Jack Wilson]

Right. Okay, so let me kind of sum up here a little bit before we take our break. Your book, I notice, has, to use the formulation would have met and that kind of thing, because, as you say, you're not fictionalizing anything here. And we don't know for sure when or where that they would have met. We just know it's likely that they would have met. We do know with certainty that they knew one another because Shakespeare dedicated his two long narrative poems to Southampton, and he's been frequently identified as the fair youth of Shakespeare's sonnets, and he would match his age and physical features and personality and so on. But did I miss anything there? Is there more evidence that we have, or should we take our break? And then I want to ask you about how Southampton could have helped Shakespeare.

[David Medina]

I think just from a literature perspective, you're right that there are strong connections between Southampton and the two first published narrative poems and the sonnets. The evidence I found, what I argue in my book, is also that Shakespeare wrote two of his plays for and about Southampton as well, All's well that Ends well and the Merchant of Venice. But we can leave it there and pick up again after the break.

[Jack Wilson]

Okay, let's take a quick break and come back with more from David Medina.

[David Medina]

Foreign.

[Nordstrom Ad]

This episode is brought to you by State Farm. Knowing you could be saving money for the things you really want is a great feeling. Talk to a State Farm agent today to learn how you can choose to bundle and save with a personal price plan. Like a good neighbor, State Farm is there. Prices are based on rating plans that vary by state. Coverage options are selected by the customer availability, amount of discounts and savings and eligibility vary by State.

[State Farm Ad]

Shop 4th of July Savings at the Home Depot right now and get up to 40% off plus up to an extra $600 off select appliances with free delivery like Samsung from all in one washer dryers to smart refrigerators. Upgrade to tech you can trust with Samsung appliances. The Home Depot has what you need to simplify your routine. Don't miss 4th of July appliance saving savings at the Home Depot. Free delivery on appliance purchases of $396 or more. Offer valid June 18 through July 9, US only. See store or online for details.

[Jack Wilson]

Okay, we're back. So, David, I wanted to ask how Southampton might have helped Shakespeare further his career, but now I'm kind of interested in in the two plays and what you've discovered. How do you know that Shakespeare wrote those two plays kind of for and about Southampton?

[David Medina]

Well, you know, just starting with Allsworth ends well, which Shakespeare wrote in around 1602. He portrayed Helen, one of the two lead characters, as a caring and intelligent woman deeply in love with someone of a much higher status. And that's exactly the position that Shakespeare found himself at that time being in love with the much higher ranked Southampton. But there are also several clear and undeniable similarities between Henry Risley, 3rd Earl of Southampton, and Bertram, the Count of Roussillon in this play, and they don't get mentioned very much in biographies. Both were royal wards of the state. Bertram and Henry both fought arranged marriages, both fought in foreign wars, both held the same military positions, general of the horse. And both were young, attractive and extravagant. And so it just changes your view of that play if you think about how Shakespeare is describing Bertram, Count of Roussillon. But I also believe that Shakespeare depicted himself in the Merchant of Venice as well as Antonio, who is a self described actor in love with his best friend Bassanio and portrayed Southampton as Bassanio, who's described as an educated and noble military man like Southampton, who ultimately marries a woman but is still more in love with Antonio. And you have to know the backstory of what was happening in Shakespeare's life when he wrote the Merchant of Venice in around 1597. Again, he was still very much in love with Southampton, who was unfortunately courting his future wife, Elizabeth Vernon at this time, just as Antonio was pining over Bassanio while Bassanio was courting and marrying Portia. And so there's just all of these connections between again, this artist and his patron that go well beyond what is usually written about, which is the connection into sonnets. I believe they go beyond the sonnets to at least two narrative poems and to at least two of his plays. So that leads me to argue overall that Shakespeare wrote more of his plays and poems for and about Southampton than anyone else.

[Jack Wilson]

Right. Did anybody comment on this? Or if not, what do you make of the fact that nobody did? Was it something that they had to keep secret? Or do you think it was sort of an open secret that no one commented on? Maybe just because we don't have enough evidence people weren't writing enough letters and so on, or that they were trying to protect the two of them and say, we don't want to get you in trouble, so we're not going to kind of say, oh, by the way, Shakespeare and Southampton have been cavorting about London again, or whatever we could imagine.

[David Medina]

They might say, yeah, we're all familiar with sort of the overall framework of the sonnets. There's an older narrator, a younger fair youth and, and a dark lady. But in 1594, three years into the relationship between Shakespeare and Southampton, there was another contemporary work published called Willoughby His A Visa by an Unknown Author. And that long narrative poem also describes a sexual three way relationship, just like the sonnets do, involving Shakespeare, Southampton and an unknown woman. And so those characters in this work are described as one is described as W.S. an older player and player. And the second male character in Willoughby, his Elvisa is described as W.H. and Henry Willoughby Espellensis. The discreet yet clear references to Shakespeare and Southampton's relationship at the time. And in this work there relationship, sexual relationship with a character named Avisa. Just as in the sonnets, the character referred to the so called dark lady. So there was a contemporary work that called out their relationship, described it in a way that the sonnets do. So I believe there's evidence that. That this relationship was well known.

[Jack Wilson]

Now, Oscar Wilde thought that there was a W.H. the Mr. W.H. of the sonnets, I guess it was, or the dedication around those. Was William Hughes an actor? Were you able to rule him out?

[David Medina]

You know, most Shakespeare biographies and references to him, like this Oscar Wilde one you just referenced, their analysis is largely centered around the sonnets. I think to really understand and to answer the question, who was Shakespeare's greatest love? You have to look across his literature, his life and his legacy, not just the sonnets.

[Jack Wilson]

Yeah.

[David Medina]

And so, you know, for example, the evidence I present in my book, I believe makes the argument that Southampton had the most significant impact on Shakespeare's life.

[Jack Wilson]

Yeah.

[David Medina]

That is largely driven by what Nicholas Rowe, Shakespeare's first biographer, wrote that Southampton provided Shakespeare with a thousand pounds.

[Jack Wilson]

Yeah. Right. Okay, so let's talk about that, because that was something that kind of fascinated me. What was Southampton able to do for Shakespeare and what evidence do we have for it?

[David Medina]

Yeah. So again, Nicholas Rowe was his first biographer. He said that Southampton gave Shakespeare £1,000. He wrote that in his first biography that is worth about $5 million today, according to the Measuring Worth Foundation.

[Jack Wilson]

Wow.

[David Medina]

And so what was Shakespeare able to do with that at that time? Well, in May 1594, Shakespeare paid approximately £50 for a founding share of the Lord Chamberlain's Men acting company. Shakespeare could not have afforded this investment without Southampton's financial support. You know, at the time, the standard payment for a new single authored play was around six pounds.

[Jack Wilson]

Yeah.

[David Medina]

And there was no royalty system in place back then. And by 1594, Shakespeare had only written about seven plays.

[Jack Wilson]

Yeah. And he's not the author at that point of Lear and Othello and. Right. All of those came later. So it's not like he's sort of rewarding, well, here's the grand lion of our theater kind of thing. It's more like, here's somebody with promise or here's somebody I feel close to.

[David Medina]

No, exactly. And you know, this is before the Globe Theater as well. So you know, Shakespeare didn't have large amounts of money coming in, but you know, because of that thousand pound gift, he was not only able to pay for a share of the Lord Chamberlain's men, but in October 1596 Shakespeare also paid about £30 to secure approval of his family coat of arms. And again, Shakespeare did not have the funds to pay £30 for a non essential expense. So he, he needed Southampton's financial and political support. I think we have to remember that, you know, Shakespeare worked in one of the most socially stigmatized professions at the time and so lived in one of the most socially stigmatized parts of London, you know, at the time shortage. But the Risleys were one of England's oldest and richest families. They're the ones Southampton, 3rd Earl of Southampton in particular. He is someone who could have secured the coat of arms for Shakespeare and his family. And. Yeah. And then finally, you know, what else did Shakespeare likely do with this thousand pound gift from Southampton? Well, in May 1597 he paid £120 to purchase new place in Stratford upon Avon, the second largest residence there. He did not have the funds in 1597 to pay for, you know, a home that large and that expensive. So, so what it, what was Southampton responsible for the Lord Chamberlain's men's share, the Shakespeare coat of arms, the Shakespeare New Place residence. And again these are these documents, these payments are all in surviving documents that you can all find on Shakespeare documented the collaboration between the Folger Shakespeare Library and the Shakespeare Birthplace Trust and the UK National Archives. It's all there.

[Jack Wilson]

Right. And it doesn't seem like in thinking about how much we owe to Southampton for giving Shakespeare that money. It doesn't seem like such a stretch to think that it enabled Shakespeare to write a lot of the plays that we now revere as being some of the cultural touchstones of Western civilization.

[David Medina]

Exactly. It made that all possible. And as you noted a few minutes ago, Shakespeare also had a wife and three kids back in Stratford Upon Avon. He was having to support two households, one there and his own in London. And so he did not have the funds on top of keeping those two households going to pay for these other expenses and to have the mental bandwidth to write the plays that he had yet to write.

[Jack Wilson]

Right, okay. So your book describes a 25 year personal and professional relationship between the two. Can we tell how it evolved over time? I mean, did their connection to one another deepen or at some point did they become less personal and more professional? Or what do we know about this 25 year span.

[David Medina]

Well, you know, we've so far covered Southampton's impact on Shakespeare's life and literature, But I think there's a third part to this story which is his impact on Shakespeare's legacy. So in the early 1600s, there is strong evidence that Southampton was responsible for and helped Shakespeare secure his King's Men life portrait and funerary bus commissions. So In May of 1603, King James the First made the aristocratically supported Lord Chamberlain's Men the King's Men. And that commission that survives has a marginal note referencing Shakespeare but no other English actor, even though his colleagues were more prominent and wealthier. This commission also came the day after King James I pardoned Southampton for all of his offenses against Queen Elizabeth I, most notably his participation in the failed Essex Rebellion. And so, not only the commission itself, but the marginal note on the commission referencing Shakespeare, I believe point to Southampton playing a role in King James I making Lord Chamberlain's Men his primary acting troupe. A few years ago, the Shakespeare Birthplace Trust also concluded that the only Shakespeare life portrait made from life, which is now known as the Cobb Shakespeare portrait, was commissioned by Southampton. Southampton was a well known patron of portraiture. He commissioned at least 20 oil paintings and four oval miniatures and engravings of himself. And that's more than just than any other Elizabethan figure except for the Queen and the Cobb Shakespeare. And the Cobb Southampton portraits still reside together in Hatchlins park, just southwest of London. And then finally, I also believe there's a strong evidence that Southampton likely commissioned Shakespeare's funerary bust in Holy Trinity Church in Stratford. Shakespeare left no funds for a monument in his will. It was common at the time for arts patrons to help immortalize their proteges in this way. And I would say very tellingly, the bust was carved by someone named Gerhard Jansen the younger. And this was the son of Gerhard Chanson the elder, who created the Southampton sculpture of the 3rd Earl of Southampton as part of the Risley family monument in their home church in Titchfield, England, back in 1594. So to just give an overall framework of their relationship, you know, I believe the evidence points to them meeting for the first time in around April 1591. Their relationship was strongest during the period between 1592 and 1594. This is the two year period when, as we were discussing earlier, Shakespeare wrote many of his sonnets, when he wrote his first two published narrative poems, Venus and Adonis and the Rape of Lucrece for and about Southampton. And this is also during the period when Southampton likely gave Shakespeare the thousand pounds and that he used to pay for his coat of arms and Lord Chamberlain's men's share and a New Place. And you know, there's also strong evidence that Shakespeare likely lived with Southampton during this two year period. This is when he was writing those poems, those sonnets. This is when London area theaters were closed for this two year period due to continued outbreaks of the plague. And Southampton, there's other evidence showing that he housed two other poets at different times in his life. John Florio, his Italian tutor, and Thomas Heywood. So relationships started in 1591, strongest in 1592-1594, and then from 1594 till Shakespeare's death in 16. This is when I believe, based on the evidence, he wrote those two plays for and about Southampton. The Merchant of Venice and All's well that Ends well. And this is also the period when I believe, based on the evidence, that Southampton likely helped Shakespeare secure his King's Men life portrait and funerary bust commissions.

[Jack Wilson]

It's a beautiful love story. The idea that they were kind of Shakespeare kind of inspired by him and Southampton kind of betting on Shakespeare, so to speak, and recognizing his talent and wanting to enable it and nurture it, empower him to write these plays. But also this idea that the younger man outlived him, but kind of did his best to make sure that people recognized that Shakespeare had been as great as he was. We think of it now as being inevitable that of course these plays would have survived and of course they would have become part of the canon and so on. But as I've learned, when we had a bunch of guests who were here to talk about the anniversary of the First Folio, Theater was so transient back then and things would just disappear. And there wasn't necessarily a set of plays etched in stone that had been published and were recognized and they would morph and change and then they would kind of disappear if people weren't putting on productions. And for somebody to have a life portrait and a funerary bust and to just kind of keep that person in the public eye as someone who was a little more worthy than the others, might have helped us make sure that Shakespeare's plays survived to the extent that they did.

[David Medina]

I agree, I agree. And you know, what I'm still struck by though, is as far as I know, no other book has focused on what I believe is an important literary and historical question, which is who was Shakespeare's greatest love? There are books every year written about Shakespeare's family, his childhood home, his religion, his Wife. The number of swear words in his work works, you know, even whether Shakespeare was Shakespeare. Not on What I believe at its core is inherently a very important question when you're talking about the man who wrote the song.

[Jack Wilson]

Right. Romeo and Juliet. Yeah. Who gave us so many different loving relationships and so many different stages of life.

[David Medina]

And the lack of books devoted to this greatest love question is not due to a lack of evidence. I include more than, you know, 200 endnotes in my relatively brief book that collectively help prove that Henry Risley, 3rd Earl of Southampton, was Shakespeare's greatest love. Why has no one ever collected those facts in a comprehensive way like this?

[Jack Wilson]

Well, why do you think that is? And I'm going to suggest that uneasiness about this being a same sex relationship might have been part of it.

[David Medina]

I agree. You know, some Shakespeare biographers and editors, you know, over the last 400 plus years have probably believed that there wasn't sufficient evidence to answer this greatest love question. And I believe I've shown that to not be true. Some didn't think it was important to know who might have inspired at least some of Shakespeare's works. And I believe that is unfortunate. But, but as you were just noting, you know, some knew that if they did wade into this greatest love question, this topic, they would be forced to highlight the same sex, love and desire that's so obvious in so many of the Bard's poems and plays. And to take it one step further, I also believe that, you know, far too many writers have chosen not to address this question because they believed it would be too controversial for their PhD advisors and then later for their publishers. I didn't have those barriers before me. I wanted to find the truth. I didn't come to this with any assumptions. I'm not a lifelong Shakespeare expert biographer. I followed the evidence and it became so clear to me that the answer to this question was Southampton that I decided to go public to write about it.

[Jack Wilson]

Right. So what do you say to the listeners? And I will often hear from them as well, who will say, well, ultimately, what does it matter? The plays are the plays. The plays stand on their own. Who cares what you know? I mean, we might all be interested in Shakespeare from a gossipy standpoint or because we love biographies of great people. But how does it change our relationship with Shakespeare's works?

[David Medina]

I do not believe that anyone can truly understand his masterpieces without understanding the man. Who was he? What was he worried about at the time? Who was he most in love with? Those all bleed into his works and that's why I've been a lifelong reader of political biographies. I wanted to know how people made decisions, who they were, what their backgrounds were, because you can always see connections to their public policy positions and to. And to what they seek to do in the public arena. I think the same is true across arenas, across issue areas.

[Jack Wilson]

I think for when it comes to Shakespeare, I think we're. I mean, there's always a possibility that some letter is discovered in an attic somewhere or something. But for the most part, I think people have trolled, you know, dug the mines for whatever they could find. But Risley would be different, I would guess. I mean, maybe. Do you know of any papers or records or anything that are out there that maybe have been locked away? But if scholars were a little more on the hunt for looking for someone who was this connected to Shakespeare, is there anything we could hope for in the future that might shed a little more light onto this?

[David Medina]

You know, if I could wave a wand and create or find new pieces of evidence, I would want to find letters like you're describing. You know, there are many similarities between the relationship between Southampton and Shakespeare and Michelangelo. And someone named Tommaso di Cavalieri is also a much younger, beautiful aristocrat. The, you know, sonnets that Shakespeare wrote for and about Southampton survive, just as the sonnets that Michelangelo wrote for and about Tommaso survive. The plays that Shakespeare wrote for and about Southampton survive, just as the drawings that Michelangelo drew for and about Tommaso survive. But there are several letters between Michelangelo and Tommaso that survive that show sort of the endearing nature of their relationship. And no letters between Shakespeare and Southampton survive. There are a few letters in Southampton's hand that survive. None of them reference Shakespeare, but I believe that would have been common at the time artists wrote for and about their patrons. It usually didn't happen in reverse during the lesbian era.

[Jack Wilson]

Right, okay. So. Well, we will hope that it seems like we do get discoveries every few years or so, and maybe something will surprise and delight us all. In the meantime, we can enjoy Shakespeare's greatest love, the book by our guest today, author David Mednina. David Medina. Thank you so much for joining me on the History of Literature.

[David Medina]

I loved it. Thank you so much.

[Jack Wilson]

And that will do it for this episode of the History of Literature. My thanks to David Medina for joining me. You can find him on tour, follow the link in our show notes, or go to greatestloves.com events to see what he's up to. And speaking of events, we will soon be telling you all about our trip to Literary England in May of 2026. Will Shakespeare be on the agenda? Of course he will be, and other great authors too. But really, the thing I'm looking forward to the most are the people we'll meet up with, some past guests of the show, and I can't think of a better traveling party than you. The History of Literature Podcast listeners. It's going to be the highlight of my year, I am sure. I'm so glad we're going to be able to offer this, and I hope you can find some room in your calendar and your budget to join us for what should be a very fun and enlightening week. Send us an expression of your [e-mail] j a c k e wilson author gmail.com or go to historyofliterature.com and the contact page. I'm Jack Wilson. Thank you for listening and we'll see you next time.

[Real Organic Podcast Ad]

Did you know not all organic food is created equal? While we trust the organic label to mean soil grown, pasture raised, and ethical, industrial agriculture is quietly rewriting the rules. That's why the Real Organic Podcast, produced by the Real Organic Project, is cutting through the greenwashing to expose the corporate greed that is reshaping organic food and farming. Each episode brings you in depth conversations with farmers, scientists, and advocates working to protect organic standards in the US without corporate shortcuts or industrial loopholes. Follow the Real Organic Podcast on Apple Podcasts, Spotify, or wherever you get your podcasts.

[No Small Endeavor Podcast Ad]

Lee C Camp here. If you've been enjoying this show, I think you might enjoy my podcast, no Small Endeavor. Produced by Great Feeling Studios and prx, no Small Endeavor explores what it means to live a good life. We sit down with courageous, impassioned people like actor Martin Sheen or civil rights hero James Lawson to ask what it means to live a life worth living. Follow no Small Endeavor Wherever you get your podcasts. Living a good life is no small endeavor and we would love to help.