Shakespeare's Greatest Love

by David Medina

Relying on historical and literary evidence hidden in plain sight, Shakespeare's Greatest Love tells the true, uncensored love story of William Shakespeare and Henry Wriothesley, 3rd Earl of Southampton.

"Shall I compare thee to a summer's day? Thou art more lovely and more temperate."
—­Shakespeare's Sonnet 18, written for and about Southampton.

Leaving behind a wife and three young children in Stratford-upon-Avon, Shakespeare moved to London for its thrilling theater scene, where everyone mixed freely across ages, classes, and ranks.

It was through their mutual passion for the theater that the handsome twenty-seven-year-old playwright first met and fell deeply in love with the effeminate seventeen-year-old earl who beguiled men and women alike and avowed that 'desire and pleasure [should] sometimes triumph over reason.'

Author David Medina demonstrates that Shakespeare wrote more of his plays and poems for and about Southampton than anyone else—works that are sexually charged, romantic, and homoerotic. He also chronicles the evidence that Southampton provided Shakespeare the support he needed to secure his acting company share, coat of arms, family residence, royal commission, life portrait, and funerary bust.

Shakespeare and Southampton's personal and professional relationship evolved privately and publicly over a quarter century against the backdrop of a national anti-sodomy law, multiple plague outbreaks, unexpected pregnancies, rushed and possibly forced marriages, a failed rebellion, and political imprisonments.

Shakespeare's Greatest Love challenges us all to recognize Southampton as the individual who had the most significant impact on Shakespeare's life, literature, and legacy.

Genres: Nonfiction

132 pages, Kindle Edition

Published April 22, 2025

About the author

David Medina has more than thirty years of national policy and political experience in Washington D.C.. He has held senior roles in the White House, U.S. Senate, national labor and civil rights organizations, and presidential campaigns. He is a cofounder of Results for America, a national organization that helps governments at all levels build and use evidence and data. David received his B.A. from the University of Chicago and M.P.P. from Harvard’s Kennedy School of Government.

Reviews

[Kristen Araujo]

Such a great read! This book provides lots of insight into the life of Shakespeare and one of the many driving forces of his work! Highly recommend!

[Jacqueline]

This book provides insight into the significant role love plays in everyone’s lives including Shakespeare’s.

[Andrew Souvall]

Thanks to David Medina for shedding light on a topic that literary historians have skirted around for too long. It really is amazing to me that so many books have been written about the world's most famous writer and yet this book is the first to focus on the relationship between Shakespeare and Henry, the Third Earl of Southampton.

I really enjoyed reading about the many references to Southampton in Shakespeare's writing --including both his poems and two of his plays -- the Merchant of Venice (one of my favorites) and All's Well that Ends Well. The detailed writings about the two plays were of particular interest to me.

The most compelling part of the book for me was when Medina focused on Southampton's contribution to Shakespeare of what would now be $5 million. As Medina wrote, "This multi-dollar gift altered the trajectory of Shakespeare's life, literature, and legacy more than any other single event. Having faced financial difficulties his entire life, Shakespeare would've been awestruck by Southampton's unbelievable generosity."

I also found the section on Southampton's time in the court of Queen Elizabeth I very interesting, particularly the part where a close associate of Lord Burghley's attacked Southampton as a homosexual because Burghley was upset that he would not marry his granddaughter.

With all of these tea leaves, it's hard to believe that nobody has made this connection before. Bravo to Medina for this book. It finally addresses a part of Shakespeare's life that too many authors have ignored.

[John P.]

A Bold, Breakthrough Analysis Of Shakespeare’s Life That Challenges Antiquated Historical Lenses

As an avid Tudor history buff, I have a high regard for historians who challenge accepted historical narratives with alternative possibilities based on new evidence or looking more closely at evidence in plain sight (see e.g., Alison Weir’s fantastic book “The Lady in the Tower: The Fall of Anne Boleyn” and Anne Somerset’s excellent biography “Elizabeth I”). I was pleasantly surprised to come across this book that challenges assumptions about Shakespeare’s sexual life and the strong evidence that historians have ignored or not considered regarding his romantic relationship with Henry Wriothesley, a man who he knew for over 25 years and who financially, politically, and emotionally supported Shakespeare’s life and world famous works. And why have historians ignored the significance of this relationship? Will they only acknowledge Shakespeare’s sexuality and relationship with Wriothesley if he had actually came out and said it? Here the author weaves together a convincing case based on solid evidence. The author’s writing style is crisp and elegant. It’s a concise and arresting read. It certainly presents enough intriguing material to warrant a TV series or movie. I’m glad that the author is shaking things up on this topic. It’s a refreshing book that does not disappoint and is sure to generate much needed discussion.

[Alex Araujo]

Thank you David Medina for showing us that Shakespeare’s Greatest Love was an effeminate earl named Henry Wriothesley, 3rd Earl of Southampton. I didn’t know that Shakespeare called Southampton- ‘ lord of my love’- in the dedication of his second published work until I read Shakespeare’s Greatest Love. Bravo to David Medina for doing what no other Shakespeare biographer has done — focus us all on the important literary question: ‘ Who was Shakespeare’s Greatest Love?’ Truly inspirational!

[Bill]

A compelling view into a seldom discussed aspect of Shakespeare’s life. The author explores Shakespeare’s relationship with his patron, Southampton, and also his relationship with his wife and children. If you are a Shakespeare fan, read this book.

History has a way of obscuring so many details of the lives of historical figures. Thank you to the author, Medina, for restoring some clarity through his research.

[Elizabeth T]

A great read! David really changed the game with this book. I never considered Shakespeare’s muse could be a man, but this book really opened my eyes to see more deeply into his works. It delves into the backgrounds of both Shakespeare and Henry and provides lots of evidence that points towards true love. So much emotion, I was truly intrigued chapter after chapter. Good work David!

[Reader]

Shakespearse’s Greatest Love was an amazing read. Medina combines history and so much passion into his book that makes it unable to put down. I’m a long time Shakespeare fan but can also say can say that anyone would be captivated by Medina’s book.

[Linda MT]

Truly insightful view into what really inspired Shakespeare!

[Guillermo D T]

Excellent book by David Medina that explores Shakespeare’s personal life and reveals what inspired his thrilling work!

[Juliana T]

Bravo David Medina for doing what no other Shakespeare biographer has done -- focus us all on the important literary question: 'Who was Shakespeare's Greatest Love?'

[Deb Stern]

or was it Emilia Bassano writing for Shakespeare who loved Southhampton?
Check out Jodie Picoult's book "By Any Other Name"

[Carmen Anta]

Learned so many things about Shakespeare’s love.. I am excited to keep reading!

[Mike J]

Learned so much about Shakespeares true love. Must read for all Shakespeare fans!

[Pankti]

Give me more stories about historical figures being gay

[Guillermo Tapia]

Truly enjoyed reading about Shakespeare’s true love and what inspired him.

[Ellie Hope]

some of the most egregious misuses of the word "undeniably" I've ever read

[Garry Potter]

A fascinating read. Great insight into Shakespeare, his poetry, and relationship with Southampton.

[Chris Tilden]

For anyone interested in the life of William Shakespeare, this tidy little read (100 pages) is a must. I am not in any way well read in regard to Shakespeare's biography, so I enjoyed getting to hear some of the background of one of England's greatest writers. I don't think it is a "spoiler" to say that the primary theme of this book is the importance of the relationship between Shakespeare and aristocrat Henry Wriothesley, one of Shakespeare's patrons. The author believes that there was a close (and romantic/sexual) relationship between the two men, something the author feels has been almost completely overlooked by other scholars. While I enjoyed the book, one thing I found a bit irritating was the tone of this book, which seems somewhat hostile to other scholars and, honestly, a bit egotistical. In the introduction, the author states that, "In the following pages, which are grounded in historical and literary evidence hidden in plain sight but ignored, minimized, and attached throughout history, tell the true, uncensored story..." The epilogue closes the book, stating, "The preceding pages have presented the true, uncensored story of how Henry Wriothesley, 3rd Earl of Southhampton, became Williams Shakespeare's greatest love..." Ah, truth. I'm always a bit skeptical of anyone who feels only they have the unvarnished truth. This would not have bothered me so much in this book, if it wasn't so painfully obvious how much the author wants you to believe his claims, sometimes using circumstantial evidence. For example, at one point the author states that Wriothesley "likely commissioned Shakespeare's bust in the chancel of the Holy Trinity Church." Likely. Not definitively. I'm not saying this to try to discredit or argue with the points made by the author. The book appears well-researched and the author may have a valid claim. I also couldn't help but wonder if the author has read Jodi Picoult's latest work, "By Any Other Name," and what he thinks of it. Ms. Picoult's book is based on the premise that the reason for there is so much passionate language and "language of love" in Shakespeare's work because it was written not by Shakespeare but by a woman, under his name. I found that to be an intriguing premise as well. But I digress. This is definitely a worthwhile read for anyone interested in the Bard. You can get through it in a few hours and learn a few things about Shakespeare, some of which, I imagine, is actually the TRUTH. Enjoy...