Exit, Pursued by a Barrister:
What Shakespeare Tells Us About Tyranny, Liberty, and the Rule of Law
The 2026 Asa Gray Lecture
Thank you for your invitation to deliver the 2026 Asa Gray Lecture. I’m deeply honored. Given some of the speakers you’ve invited in prior years, I’m also feeling deeply unworthy.
Your invitation inspired me to learn more about Asa Gray, which alas did nothing but intensity my feelings of unworthiness. What a remarkable person. Groundbreaking botanist; friend to many of the leading figures of his day, including Charles Darwin and James Russell Lowell; and, of course, founding faculty member of the University of Michigan.
The story goes that on the occasion of Gray’s 75th birthday, Lowell sent him a little poem that read as follows:
“Just fate, prolong his life, well spent,
Whose indefatigable hours
Have been as gayly innocent,
And fragrant as his flowers.”
Now, that describes a life well lived. I’ll do my best to honor that extraordinary life in my remarks this evening.
A while back, I read an article by a seminary professor who found himself in a conversation with his airline seatmate. This happens to those of us who travel a lot. The stranger asked the professor what he did for a living, and he responded that he was a theologian. The puzzled seatmate replied: “Really? Well, what exactly do theologians do?” The professor pondered the question for a moment and then answered: “We think about everything.”
As someone who has darkened the doors of several seminaries, I agree that theologians have a strong claim to that effect, but I don’t believe it’s an exclusive one. In law school, we think about pretty much everything, too. And I’m familiar with at least one individual who seems to have spent most of his life doing so as well: His name was William Shakespeare.
At the law school, I teach traditional doctrinal courses in things like procedure, evidence, ethics, and First Amendment. But I also teach a much less traditional course on Shakespeare and the Law. And this year I’ve published a book on the subject, the title of which capitalizes on an irresistible pun: It’s called Meeting Shakespeare at the Bar.
My book is about the intersections between Shakespeare’s plays and some of the questions of politics and law that matter, or at least should matter, to all of us—regardless of party affiliation. Those include questions like: How do we know when we have a tyrant on our hands? If we think we do, then what should we do about it? Can we count on the resilience of our political and legal structures to see us through the crisis? What are the qualities of character in public officials that make tyranny possible? Is there a bulwark that stands between liberty and authoritarian rule? If so, then what is it and how do make sure it’s working?
These questions are discussed and debated in the media these days, on talk shows and in the editorial pages of newspapers and in books and on podcasts. Shakespeare’s plays remind us that they are very old questions. And his plays help us think deeply and critically about them. I heard an interview with a prominent Shakespeare director who said something with which I strongly agree: Wherever we go in our thinking, we will find William Shakespeare already there waiting for us.
Having said that, let me add a word to help set expectations. Shakespeare was much more interested in exploring the complexity of these questions than he was in providing simple and straightforward answers to them. I suspect that he doubted whether such answers to those questions exist. Many of us may have arrived at the same conclusion.
In any event, that’s how I’d like to spend our time together tonight—by bringing you on a tour of these sorts of questions in the company of my old friend, Will. I’ll talk about four of his plays: Julius Caesar, Macbeth, Measure for Measure, and Henry VI, Part 2. And we’ll see what they have to say to us about some issues that may be on our minds.In so distinguished a group as this it’s entirely plausible that some of you know these plays better than I do. But don’t worry if you’re not familiar with some or even all of them. Along the way, I’ll give you quick summaries of the relevant plotlines. They’ll necessarily be brief but also sufficient to our purposes.
Will has lots of ideas. I’m sure you’ll have some, too. So I’ll try to leave some time at the end for a little conversation.
Most or all of you are probably familiar with Julius Caesar, so let’s start there. As you’ll recall, the story is set in ancient Rome and it begins with Julius Caesar busily amassing power in ways that worry those who want to preserve the republic. The patricians Cassius and Brutus discuss their concerns, and Cassius invites Brutus to join a conspiracy to assassinate Caesar. After some initial hesitation Brutus agrees, and Caesar is bloodily slain. In the end, however, these events set the stage for Octavius to seize power and to establish an empire—the exact outcome Cassius and Brutus were trying to prevent.
Throughout history, many people have understood Julius Caesar as a muscular testament against tyranny and authoritarianism. In 1937, Orson Welles staged a modern dress version of the play in which he depicted Caesar as Benito Mussolini. When, in the apartheid era of the 1970s, an edition of Shakespeare’s plays was secretly circulated among the prisoners on South Africa’s Robben Island, Nelson Mandela wrote his name next to Julius Caesar. The contemporary Broadway play Good Night and Good Luck, about Edward R. Murrow’s fight against McCarthyism in the 1950s, repeatedly quotes from Julius Caesar.Like all powerful influences, this one has sometimes gone tragically awry: Enthusiastic fans of its anti-tyranny message include a man by the name of John Wilkes Booth, and we all know how that turned out.
My own view, however, is that Shakespeare wants us to understand the full complexity of the moral dilemmas that an embryonic tyrant can present to us. Indeed, the early soliloquy in which Brutus persuades himself to join the conspiracy to kill Caesar may leave us profoundly uneasy and not at all reassured. Listen to what he says:
“It must be by his death. And for my part
I know no personal cause to spurn at him,
But for the general. He would be crowned:
How that might change his nature, there’s the
question.
It is the bright day that brings forth the adder,
And that craves wary walking. Crown him that,
And then I grant we put a sting in him
That at his will he may do danger with.
Th’ abuse of greatness is when it disjoins
Remorse from power. And, to speak truth of Caesar,
I have not known when his affections swayed
More than his reason. But ’tis a common proof
That lowliness is young ambition’s ladder,
Whereto the climber-upward turns his face;
But, when he once attains the upmost round,
He then unto the ladder turns his back,
Looks in the clouds, scorning the base degrees
By which he did ascend. So Caesar may.
Then, lest he may, prevent. And since the quarrel
Will bear no color for the thing he is,
Fashion it thus: that what he is, augmented,
Would run to these and these extremities.
And therefore think him as a serpent’s egg,
Which, hatched, would, as his kind, grow
mischievous,
And kill him in the shell.”
In essence, Brutus says: “Well, I haven’t seen any evidence that Caesar wants to become a tyrant, but he’s an ambitious guy, and you know how ambitious guys are, so it’s best to nip it in the bud.” As reasons for committing cold-blooded murder go, Brutus’s may leave us unimpressed.
Brutus’s argument includes another worrisome dimension that he doesn’t seem to recognize, a paradox of sorts that I discuss in my book. Brutus joins the plot to assassinate Caesar in order to try to preserve the political and legal structure of republican Rome. But, of course, the act of assassination itself lies outside of the very political and legal structure that Brutus hopes to save. In other words, Brutus concludes that he needs to break the law to preserve the law. We hear similar arguments today during debates over the use of civil disobedience as a form of protest and dissent.
Shakespeare didn’t write a play that clearly tells us whether Brutus was right or wrong—what’s the fun in that? He instead wrote a play that rejoices in the spectacular moral ambiguity and messiness of the situation. So, here, bounce back and forth with me a little.
Maybe Brutus is wrong: Departing from the law to save the law creates a dangerous precedent, and it’s not clear who has the authority to decide it’s necessary. Or maybe Brutus is right: If our slavish obedience to the law costs us the law, then the law becomes a kind of political suicide pact; surely, the law doesn’t require us to stand by passively while a tyrant dismantles the law piece-by-piece. Or, again, maybe Brutus is wrong: In the end, both he and Cassius take their own lives; so, their departure from the law to save the law turns out to be a kind of suicide pact, too.
What’s the answer to this collection of dilemmas? Shakespeare doesn’t tell us. He wants us to struggle with the complexity of the situation right along with him.
As I said, Shakespeare is much less interested in telling than in asking. And he’s also much less interested in telling than in showing.
That brings me to the second play I want to discuss, another I’m sure all of you know, Macbeth. Full disclosure, this is my favorite of Shakespeare’s plays. And why not? It’s got everything: It’s short. It has tremendous energy. It has witches. It has some of the Bard’s best poetry.
Really, does Shakespeare—or anyone else—give us anything better than Macbeth’s words on learning of the death of his wife?
“Tomorrow and tomorrow and tomorrow
Creeps in this petty pace from day to day
To the last syllable of recorded time,
And all our yesterdays have lighted fools
The way to dusty death. Out, out, brief candle!
Life’s but a walking shadow, a poor player
That struts and frets his hour upon the stage
And then is heard no more. It is a tale
Told by an idiot, full of sound and fury,
Signifying nothing.”
I just don’t think so.
By the way, the play even comes with its own legend—that performing it brings bad luck and we should call it The Scottish Playand hope for the best. There are numerous stories of misfortunes associated with stagings of the play, some terrible, some hilarious. My favorite tells of a performance with Peter O’Toole as Macbeth where the actor playing the servant flubbed a line, saying “My wife is dead” rather than “Your wife is dead.” The exchange went like this:
Servant: My wife, my Lord, is dead.
Macbeth: (Pause) What about my wife?
Servant: Oh, yeah, she’s dead, too.
Macbeth: (Staring)
Servant: There’s a lot of it about.
The story is unverified, but it’s too much fun not to believe that it’s true.
Here’s a quick summary of the play. Fresh from saving Scotland from insurrection, Macbeth and his friend Banquo encounter three witches. The witches predict a brilliant future for Macbeth, culminating in him becoming king. Their prophecy is partially fulfilled when the sitting king, Duncan, rewards Macbeth with a new title.
To help Fate along, Macbeth—in conspiracy with his wife, Lady Macbeth—murders Duncan and seizes the crown. The witches tell Macbeth that no man of woman born can kill him, which Macbeth understands as an expansive guarantee of personal safety. But it turns out that Fate loves a good loophole, and Macbeth is finally slain by MacDuff, who was born through Cesarian section.
As I say, most of us know the play, and that very familiarity can obscure something that I think Shakespeare wants us to see. It’s easy to miss, because we come to the play knowing how the plot unfolds and anticipating its imminent drumbeat of murder and mayhem. But I want you to notice that, as the play begins, the people of Scotland would have been thinking about things quite differently.
Consider the circumstances from their perspective. As the play opens, Scotland has survived not one but two efforts at insurrection, both put down by the brave and valiant Macbeth. He has littered the country with the corpses of Scotland’s enemies and has restored peace. Should any further trouble arise, Macbeth will no doubt summarily dispense with it in his bloody and customary way. Everything must have felt settled, stable, safe, and secure.
But then watch what happens. In quick succession, the witches forecast Macbeth’s rise, Duncan alienates Macbeth by naming his son as successor to the throne, and Macbeth confesses to us his “black and deep desires.” Within four scenes, the rule that seemed settled, stable, safe, and secure has grown fraught and fragile.
The breakneck pace continues. By the sixth scene, Duncan has arrived at Macbeth’s castle. By the seventh scene, the Macbeths have put firmly in place their plot to murder him. By the second scene of the second act, Duncan is dead. By the end of the second act, Macbeth has taken the throne. Not everyone receives this as good news; as the rebellious nobleman Angus later declares: “Now does he feel his title / Hang loose about him, like a giant’s robe / Upon a dwarfish thief.”
A funny story circulating on social media includes a nod toward the extraordinary pace of Macbeth. Apparently, an elementary school teacher introduced her students to the play and asked them to write the imaginary diary of one of its characters. A nine-year-old boy chose King Duncan. He wrote: “Day 1: excited about visiting ma wee friend macbeth and hoping he does nae kill me in ma sleep. Day 2 (ghost king): i cannae believe he killed me.” It pretty accurately captures how swiftly things rush along here.
Through that breakneck pace, Will doesn’t so much tell us something as show us something. Many of Will’s plays, especially the histories, depict a slow and gradual dismantling of power. In Macbeth, however, Will presents us with an altogether different possibility. He shows us that social and legal order is frailer and more delicate than we tend to believe and that it can vanish in a heartbeat—literally.
Furthermore, that dramatic political transformation can come even without a revolution or a formal restructuring of the social architecture. A mere switch in personnel can suffice. In one sense, everything changed when Macbeth became king; but, in another sense, nothing changed at all: monarchy yesterday, monarchy today. Some upheavals happen like that, unfolding within the very structure that they threaten to undermine.
Now, all this may sound very dark, but as I point out in the book there’s an odd sense in which Macbethis a “feel good play,” although I may be the only person you’ll ever hear call it so. After all, in the end Macbeth is defeated. The irresistible forces of justice and righteousness that exist within the Universe hound him and Lady Macbeth to an inglorious doom.
Dr. King famously said: “The arc of the moral universe is long, but it bends toward justice.” I think Macbethreflects a similar sensibility, but with one amendment. The moral universe depicted in the Scottish Play doesn’t look like the cordial angel sitting on your shoulder. This moral universe looks like a merciless juggernaut. It has teeth. And when this play’s moral universe starts bending toward justice, well, everyone had better get on board or get out of its way.
It’s coming through.
The third play I want to discuss with you is Measure for Measure. It’s a lesser-known play that was largely ignored and rarely performed for many years. Recently, artistic directors have rediscovered it and it’s experienced a resurgence in popularity, in no small part because of its connections with the themes of the #MeToo movement.
Here’s what happens in the play. The Duke of Vienna has a problem, and it’s one of his own making. Vienna has plenty of laws against things like fornication and prostitution, but the Duke has allowed them to go unenforced for a long time. As a result, Vienna has fallen into a state of moral decay.
The Duke comes up with a plan: He will pretend to leave Vienna; he will appoint his severe and puritanical deputy Angelo to clean things up; and he will disguise himself as a friar and stick around so he can see how things go. As I say in my book, the Duke has lots of ideas, and most of them are quite bad. This plan is certainly among the bad ones and things start to go wrong with it almost immediately.
Angelo begins an aggressive crackdown, strictly enforcing those long-neglected laws. Among other things, he charges one Claudio with fornication for engaging in extramarital sex with his betrothed, Juliet, even though they are on the very cusp of marriage. The charge has potentially dire consequences, because the prescribed penalty for the offense is death.
Claudio’s sister, the virtuous Isabella, puts aside her plans to enter a religious order to try to help her brother. She goes to Angelo and pleads for mercy. Angelo will have none of it; her brother must die. But in the course of their conversations Angelo begins to lust after Isabella. And so he gives her an ultimatum: Sleep with me, or your brother will be tortured and executed.
The scenes between Angelo and Isabella are almost uncomfortably modern in their sensibility. For example, when Isabella threatens to report Angelo’s efforts at sexual extortion, he dismisses her with these chilling words: “Who will believe thee, Isabel?” It’s the kind of statement we hear from sexual predators even today, men comfortable in the belief that the patriarchy will protect them, as it all too often does. In the play, Angelo finally gets his comeuppance, but we know that in real life it doesn’t always work out that way.
We can fairly describe Angelo as a tyrant. And I want to focus on a particular aspect of Angelo’s character that I think tells us something about how tyrants come into power and how they hold onto it. It’s not an element of character that Angelo has. It’s an element of character that he lacks.
To me, one of the most striking things about this play is that over and over again Shakespeare gives Angelo the opportunity to confess his errors, to repent, and to go in a different direction. He gets numerous “off ramps” from his villainy. But Angelo ignores each and every one of those opportunities.
He openly and freely lies about pretty much everything. He stubbornly persists in his terrible and malicious course of conduct regardless of the damage it does. And he keeps at it until the circumstances finally corner him and trap him beyond any escape.
At least in part, Angelo can do all of these things because he lacks the capacity for shame. Someone capable of shame would amend their conduct when confronted with the truth, with their hypocrisy, with the pain and suffering they are inflicting on others. It takes a thoroughly shameless person—like Angelo—to persist in this conduct without any hint of embarrassment, hesitation, remorse, or regret.
It reminds me of a historical moment on June 9, 1954. Senator Joseph McCarthy was conducting his anti-Communist witch-hunt hearings and imposing his own form of tyranny on America. Joseph Welch, a Boston attorney who had been retained to represent the United States Army in the proceedings, became outraged when McCarthy suggested that a young lawyer in Welch’s law firm had ties to Communism.
Welch stole the show, and probably single-handedly put an end to McCarthy’s movement and career, when he stood up and declared: “Until this moment, Senator, I think I never really gauged your cruelty or your recklessness. Let us not assassinate this lad further, Senator. You have done enough. Have you no sense of decency, at long last? Have you no sense of decency?” It was another way of saying: “Have you no shame? None at all? Is there finally nothing—nothing—that you won’t do or say?”
In our contemporary society, shame and shaming often get a bad rap, and for good reasons. We worry that those who are in charge can use shame to oppress those who aren’t. We envision Puritans forcing Hester Prynne to wear the scarlet letter “A” on her clothing to alert the world to the disgrace of her adultery.
In September of this year, Jay Caspian Kang published an article in the New Yorkerentitled: “The Death of Shame is Tearing us Apart.” In an early paragraph, he makes this statement and asks this question:
“Shame is one of the ways that groups of people mediate their norms without state intervention. This, of course, is not always a good thing. But any community without shame must have moral consensus, or else it risks splintering into the chaos of personal interpretation and individual will. How much of today’s societal collapse and atomization can be attributed to the blatant disregard for shame?”
I think Will would say: “Quite a lot of it.”
In the character of Angelo, Shakespeare shows us what happens when we put power in the hands of a man incapable of shame. It makes for an ugly lesson. And things turn out alright in the play only because that’s what it is—a performance, and a comedy at that, so it must end happily.
Interestingly, though, Shakespeare scholars debate just how happily this play actually ends: Yes, Angelo is exposed and is condemned to death; but then he is pardoned and ordered to marry his onetime fiancée, Mariana, who he had abandoned when she lost her dowry. It doesn’t seem like much of a punishment, except perhaps for Mariana.
And so it goes. The shameless have an uncanny gift for slipping through the otherwise firm and stubborn grip of Justice. This brings me to our last play, one that many of you may not know: Henry VI, Part Two. It’s among Shakespeare’s earliest works and it’s a history play, the genre in which young Will first made his mark. It reflects his inexperience as a playwright: it includes so many characters that we can lose track of them; it lurches about from one scene to another; and it’s very long. But it also shows signs of his budding genius.
Here’s a very brief synopsis. King Henry VI sits on the throne of England, but just barely. He’s a weak ruler, which creates a vacuum of power that all of the treacherous nobles surrounding him would like to fill. In sum, the play tells the story of their efforts to take the crown and his efforts to keep it. It’s a story that Shakespeare will ultimately tell over the course of several plays.
For our purposes, the most important moment in this play comes in the camp of a rebel by the name of Jack Cade. Cade is a primitive populist who leads a ragtag band of soldiers against the king in an attempt to usurp him. His followers include a number of colorful characters, such as a violent brute called Dick the Butcher. During a meeting at which the rebels plan their strategy, Dick offers up this famous suggestion: “The first thing we do, let’s kill all the lawyers.”
It was a laugh line then and it’s a laugh line now and at some point in their career every attorney has probably been gifted a coffee mug or t-shirt emblazoned with those words. But, make no mistake about it, Dick’s suggestion is a deeply sinister one and he means it to be taken seriously. Dick recognizes that what stands between a just society and tyranny is the law and that the best way to dispose of the law is to dispose of those who know how to use it.
Still, the dramatic splashiness of the “kill all the lawyers” line has caused it to eclipse a larger truth. Jack Cade and Dick the Butcher aren’t just out to kill all the lawyers. They’re out to kill anyone who is literate, anyone who has the power of language at their disposal, anyone who has the capacity to think and to express their thoughts in words. Indeed, the first person killed by Jack Cade is not a lawyer but a clerk—the Clerk of Chatham—whose only offense is that he can read and write and do basic math.
I emphasize this point because we lawyers tend to take Dick the Butcher’s statement as a kind of backhanded compliment—we, and we alone, stand between a just society and tyranny. One of Shakespeare’s most famous stage directions comes in his play The Winter’s Tale: “Exit, pursued by a bear.” It’s as if our society’s only hope against tyranny comes when law forces the tyrant to flee the political theater: “Exit, pursued by a barrister,” if you will.
But Shakespeare understood that it is the educated class more broadly that provides our greatest bulwark against tyranny. Nothing threatens a would-be dictator like a rational, well-informed, clear-thinking, and articulate human being. Nothing undermines a wannabe despot like a person of conscience who has the capacity to reason and the courage to say what they believe. You know the kind of person I mean. You’re sitting next to them.
In the end, Jack Cade’s revolution fails. Indeed, his own men turn on him. But Shakespeare was a realist, and so the play signals that there is turbulence yet to come and challenges yet to navigate. “First thing we do,” Shakespeare seems to say to us, “let’s kill all the illusions.”
The teaching of my seminar and writing of my book have given me the opportunity to marinate in Shakespeare’s thinking for several years now. I have found it a balm for the soul in troubled times. And he has taught me many things: That the ascent of authoritarianism can entangle us in problems of great moral complexity; that our political and legal structures may be more fragile and less stable than we thought they were; that one of the most dangerous qualities in a political leader is the absence of a capacity for shame; that the great bulwarks against tyranny include not just law but language itself, language as used by every human being who has the courage, the conscience, and the commitment to tap into its awesome power.
Why read Shakespeare in a time like this? Because Shakespeare’s problems are our problems. His dilemmas are our dilemmas. When in The TempestFerdinand cries out “Hell is empty, and all the devils are here!” we may know how he feels.
The great twentieth-century novelist Vladmir Nabokov was once asked to identify his favorite contemporary author. He replied: Shakespeare. The questioner persisted: I said contemporaryauthor. Nabokov again replied: Shakespeare. I couldn’t agree more.
Well, I want to wrap things up so we have some time for discussion and questions. So, let me thank you again for the invitation to be here, and for joining me and my grand old friend Will on our brief tour of this bumpy political and legal terrain. I hope it has stirred within you the whole gamut of reactions: considered agreement; friendly dissent; a basket or two of thoughts; a basket or ten of questions. If it did any of these things, then I think we have respected the inquisitive spirit of my grand new friend, Asa Gray.