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 historyofliteraturepodcast@gmail.com 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.