The Reluctant Prince: Why Harold Washington’s Story Still Matters
There’s something deeply compelling about a leader who never sought the crown but ended up wearing it anyway. That’s the essence of Prince Hal, a new play by J. Nicole Brooks coming to Chicago’s Lookingglass Theatre in 2027. Personally, I think this isn’t just a story about Chicago’s first Black mayor—it’s a reflection on the accidental heroes history often forgets. Harold Washington, a man who became mayor almost in spite of himself, is the kind of figure who challenges our assumptions about power, ambition, and what it means to lead.
A Shakespearean Twist in the Windy City
What makes this particularly fascinating is the play’s framing of Washington as a modern-day Prince Hal, the reluctant heir from Shakespeare’s Henry IV. Brooks isn’t just borrowing a name; she’s drawing a parallel between Washington’s rise and the arc of a man who steps into greatness not because he craves it, but because circumstances—and the people around him—demand it. A detail that I find especially interesting is the setting: a West Loop tavern where Washington finds his base of support among everyday Chicagoans. This isn’t just a plot device; it’s a reminder that leadership often emerges from the most unexpected places.
In my opinion, this Shakespearean riff is more than a clever literary nod. It’s a way to elevate Washington’s story, to say that his journey wasn’t just political—it was almost mythical. What many people don’t realize is how much Washington’s tenure as mayor (1983–1987) reshaped Chicago’s identity. He wasn’t just breaking racial barriers; he was redefining what it meant to govern a city as complex and divided as Chicago.
The Trilogy That’s Bigger Than Its Parts
Prince Hal is the second installment in Lookingglass’s planned trilogy about Chicago mayors, following Brooks’s Her Honor, Jane Byrne. If you take a step back and think about it, this trilogy isn’t just a series of biographical sketches—it’s a love letter to the city itself. Mayors, after all, are the architects of a city’s soul. Washington, Byrne, and whoever comes next in the trilogy are more than historical figures; they’re lenses through which we understand Chicago’s evolution.
One thing that immediately stands out is the timing of this production. Slated for 2027, it’s a reminder that Washington’s legacy isn’t just history—it’s still being written. His story resonates in today’s political climate, where questions of representation, equity, and the role of everyday people in politics are more urgent than ever.
Beyond the Stage: Lookingglass’s Bold Choices
Lookingglass’s decision to produce Prince Hal is part of a broader pattern of bold, thought-provoking theater. Mary Zimmerman’s upcoming adaptation of The Yearling—a Pulitzer Prize-winning novel about a boy and his deer in post-Civil War Florida—feels like a left turn, but it’s classic Lookingglass. What this really suggests is that the theater isn’t afraid to take risks, to pair the deeply personal with the universally human.
What’s also noteworthy is the theater’s fall hiatus, during which the space will host the commercial production of Kowalski, starring Johnny Galecki. From my perspective, this is a smart move. It keeps the theater relevant while allowing it to recharge creatively. It’s a reminder that even institutions need to breathe, to experiment, and to take risks.
Why This Matters—And Why It’s Personal
If there’s one takeaway from Prince Hal and Lookingglass’s broader season, it’s this: stories matter. They shape how we see ourselves and our world. Harold Washington’s story isn’t just about Chicago; it’s about the reluctant leaders among us, the people who step up not because they want to, but because they have to.
This raises a deeper question: What does it mean to be a leader in a time of division? Washington’s tenure was marked by fierce opposition, yet he managed to unite parts of the city that had never been united before. In a world where polarization feels inevitable, his story is a reminder that leadership isn’t about dominance—it’s about connection.
Personally, I’m excited to see how Brooks brings Washington to life. Theater has a way of humanizing history, of making the past feel present. And in a city like Chicago, where the past is always knocking on the door of the present, that’s more important than ever.
Final Thoughts
As someone who’s spent years analyzing culture and politics, I’ve come to believe that the stories we tell reveal more about us than the stories themselves. Prince Hal isn’t just a play about Harold Washington—it’s a mirror held up to Chicago, to America, and to anyone who’s ever wondered if they’re up to the task of leading.
What this really suggests is that greatness isn’t always about ambition. Sometimes, it’s about showing up, listening, and letting the people around you lift you up. That’s the lesson of Harold Washington, and it’s the lesson of Prince Hal. It’s a story that’s as relevant today as it was in 1983—and it’s one I can’t wait to see unfold on stage.
