David Medina, a prominent Washington, D.C., political figure, has turned his attention to a matter of historical significance: the sexual orientation of William Shakespeare. Medina, who is openly gay and serves as the co-founder and COO of Results for America, embarked on a 20-year journey to uncover the truth about one of the world's greatest writers. His findings are documented in his book, Shakespeare’s Greatest Love, published by Disruption Books in May 2025.
Medina, who resides in McLean, VA, with his husband, Tim DeMaristris, and their dog, Puck, shared insights into his life and work. "My husband, Tim, and I have been together for 17 years. We were married on stage at the Arena Stage theater in Washington, D.C., and named our dog Puck after Shakespeare’s character," he said. "This book was a labor of love, maybe even an obsession."
The inspiration for Medina's research stemmed from reading about Shakespeare’s possible relationship with Henry Wriothesley, 3rd Earl of Southampton. After delving into biographies and historical texts, Medina became convinced that Southampton was Shakespeare’s greatest love and profoundly influenced his work.
"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," Medina explained. "Southampton was 19 when Shakespeare dedicated Venus and Adonis to him and then 20 when The Rape of Lucrece was dedicated to him. Although there is no direct evidence they were intimate, the impact Southampton had on Shakespeare’s life and literature is undeniable."
During Shakespeare's time, homosexual acts were frowned upon by the Anglican Church and illegal under English law. However, Elizabethan society often turned a blind eye to such relationships, allowing same-sex bonds to form in a "don’t ask, don’t tell" environment.
Medina's book argues that Shakespeare’s works reflect his feelings for Southampton, with his narrative poems and several plays dedicated to or inspired by the young earl. Despite the evidence, many historians and biographers have overlooked or deliberately ignored the possibility of Shakespeare’s same-sex relationships.
"There are three main reasons why this story hasn’t been told," Medina asserted. "Some believed there was insufficient evidence, others thought it wasn’t essential, and some historians likely felt that exploring this would be too controversial."
Medina hopes his book will prompt a reevaluation of Shakespeare's life and work, encouraging a broader acceptance of the Bard's sexuality in scholarly and popular narratives.
"The truth will out," Medina quoted from The Merchant of Venice. "Nonfiction writers are responsible for writing the truth as soon as possible and sharing it as broadly as possible. I would love to see this love story acknowledged and celebrated in every medium."
Reflecting on the current socio-political climate, Medina believes Shakespeare would have expressed solidarity with contemporary LGBTQ+ struggles. "Shakespeare would have incorporated what we’re 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."
Despite the challenges, Medina remains optimistic about the future. "I believe in the strength and resilience of the LGBTQ+ community," he said. "More people are joining our fight for equality every day. Those attacking us will not win. We will win. Love will win."
The conversation around historical figures like Shakespeare highlights the importance of acknowledging and celebrating diverse identities throughout history. As Medina’s work demonstrates, the past holds stories that can inspire and empower current and future generations.
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