Lawyer Limelight: Jonathan Sherman
Photo by Eli Meir Kaplan

The only thing more interesting than being Jonathan Sherman is perhaps to be one of his clients. The Boies, Schiller & Flexner partner is Floyd Abrams meets David Boies with a side order of Hunter S. Thompson.

His passion for the law bubbles forth with astonishing ferocity, in particular about the First Amendment. His first years in practice were with Abrams, the legendary First Amendment titan of Cahill Gordon & Reindel. As a third-year associate, Sherman began to champion cameras in the courtroom as author of the brief that opened the courtroom doors to the O.J. Simpson murder trial.

But that’s not all. A voracious age of all news, all entertainment, all the time poured through those doors as well, sifted and sorted by a new media that turned on its head a publisher’s power to decide what to print. In its place came a world in which anyone could publish with no verification and little practical liability.

And in steps Sherman. He exalts the writings of Supreme Court Justice Louis Brandeis, even as he sees in them ways to protect the livelihoods of a famous editor and a best-selling author. (Sherman is also a renowned commercial and securities litigator for clients including Herbalife and Terra Firma, but that’s the subject for another day.)

Today, we’re here to talk about the art of the kill.

Lawdragon: Why did you become a First Amendment lawyer?

Jonathan Sherman: I didn’t become one. A “First Amendment lawyer” will categorically refuse to represent a plaintiff against the media in a defamation dispute, or to compel a reporter’s sources.

And drawing that line doesn’t make sense to me.  Consider Justice Brandeis.  In 1927 he issued the ur-text for all modern First Amendment law - his famous concurrence in Whitney v. California.  “Courage,” he wrote, is “the secret to liberty” - the fundamental means to “make men free to develop their faculties.”

But the Whitney concurrence wasn’t the first time he’d made that point; it was a central theme of his legal career.  In 1913, he wrote in Harper’s Weekly “[s]unlight is said to be the best of disinfectants.”  The metaphor has become American free speech gospel.  But it served an argument that should unnerve our modern First Amendment Citizens United mindset.  Brandeis’ “disinfectant” was government-compelled corporate speech—“real disclosure,” “not something which the investor could waive” - requiring financial institutions and their clients to show how they used what Brandeis called “other people’s money.”

LD: Can you explain that a little more?

JS: In Whitney, Brandeis wrote that Americans were, “self reliant,” “free and fearless,” and “recognized the risks to which all human institutions are subject.”  No one need fear today’s “evil counsels” because they may be tomorrow’s proposals to reduce those very risks.  Thus antitrust laws bar oligopolies from suffocating “the inventions of unknown men.” And securities laws - enacted 20 years after the Harper’s Weekly essay, at the pit of the Depression - require banks and public companies to be transparent to make it less likely that they will divert the money “unknown men” and women intend to use to build better mousetraps

Every lawyer’s job is to help clients assess the risks of imagining new truths and building better mousetraps.   I became that kind of First Amendment lawyer.  I help clients take and deal with risky choices, even unsexy ones, such as opposing the media or a source when it intends to publish or publishes information that punishes my client for taking risks.

LD: But it can be sexy. You’ve successfully fought to open the doors to O.J.’s murder trial, to televise the civil trial of gun manufacturers sued by the families of those killed with their weapons, and counseled CBS when the Federal Communications Commission sued over Janet Jackson’s ‘slip’ at Super Bowl 2004.

JS: High-profile cases are awesome.  But they are cases; they are always about managing risk.  Few debate that the press and social media serve a central function to protect democracy; that isn’t my point nor does it permit the media to inflict injury risk free.  So I don’t enjoy helping it, for example, use hidden cameras to seduce a fallible human being into appearing to lie when the latter has no power to explain or fight back.  What is sexy is helping those folks reclaim their reputations, or avoid damage in the first place - by serving the First Amendment.

Arguing for cameras in the courts in 2014 is no different.  I see it as the most demanding and revealing test we have of the “profound national commitment to the principle that debate on public issues should be uninhibited, robust, and wide open,” as the Supreme Court said fifty years ago in New York Times v. Sullivan.  More so than continuing the Citizens United campaign-finance debate by amending the Constitution.  We don’t need for another constitutional amendment, any more than we did in 1989 when the Supreme Court - relying on a vote by Justice Scalia - held that criminalizing flag burning violated the First Amendment.  Enough with the obsessive constitutional iconography.

The “Bill of Rights,” the Supreme Court said in 1941 was not “intended as a collection of popular slogans.”  We don’t need an amendment to save our children’s futures or to tell us who we are.  We need to re-read Brandeis as frequently as writers re-read Strunk & White.  If we do that, each of us will look into the mirror and just get on with governing and with it make things better for the days we are gone and our kids run the show.

LD: What’s the practical implication you see from that philosophy?

JS: If anyone reading this cares in the slightest that New York Times reporter James Risen is about to go to jail for refusing to disclose the confidential source(s) on which he relied to report about a botched CIA plan to slow Iran’s nuclear capabilities, then they should care a lot about cameras in the courts.  They should follow what the federal judiciary – run by federal appeals judges, especially the Supreme Court  - says about cameras in the courts.  They should stop complaining that one of the last things the Supreme Court did last term was to give a preferred position to a theory of freedom of religious worship taken straight out of the First Amendment and intended to protect Quakers from being tortured for their beliefs to give Quaker Oats and Quaker State the right not to comply with federal social welfare policy.

A half century ago in Sullivan, the Court did something similar - albeit to save the civil rights movement.  It held that the First Amendment immunized the Times from a defamation lawsuit brought by a southern “safety commissioner” as part of a strategy to cripple protesters with damages awards then handed out by Southern juries like poison Hershey’s kisses.  The Court adopted the theory of Brandeis’ Whitney concurrence: every American is a Sovereign.  Not metaphorically.  Literally.  Americans cannot be punished for criticizing the government because they, not the government, are the State.  L’etat c’est moi.   Et nous.

Until the 1994 OJ Simpson trial, those who ran the federal judiciary were at the vanguard of a constitutional revolution that fused technological upheaval with a national discussion about the paradox that America’s racial past is at odds with its founding ideals.  They did so by trying to be true to the idea of truth.  By using trials – the process of identifying truth – to think outside the paradox.  The People - and only they - were the ones to decide to deliver their news about their government to themselves.  Even before Sullivan, as the civil rights era unfolded at mid-century, the Court had repeatedly held it was up to citizens to inform themselves about government.  Whether they did so in poor taste, humiliating the judiciary, saying nasty stuff about juries, or wearing a leather jacket with the “f” word in a courthouse was up to them.

This was settled law well before Sullivan.  The last thing government was permitted to do was limit or manage debate about or criticism of the government acting with their permission.  The last place government could do it was in a courtroom.  Jury trials date back to before the Magna Carta, next year to celebrate its 800th birthday. They are about truth.  Have you ever looked at the jury during a trial?  Its sole function is to watch and listen and then decide who’s credible.  Juries are democracy’s great levelers.  Even racist ones.  They are such great bullshit detectors - the meaning of a plaintiff’s sweat, her lawyer’s sarcasm - that we require them to upend their lives even though we pay them less than the minimum wage.

LD: Magna Carta to OJ. That’s quite a historic sweep.

JS: That’s right. And by the Eisenhower Administration, the Supreme Court had overturned a string of contempt citations imposed on the press for making fun of judges.  “A trial is a public event,” the Court said in one of them, “[w]hat transpires in the court room is public property.”  In the years after Sullivan, federal appeals courts extended the “watch and learn about trials” principle to acknowledge the public’s right to monitor virtually every corner of judicial proceedings, from preliminary hearings involving minor victims of sexual assaults to jury selection.

By the Reagan Administration, the Court had held that a state’s decision to televise a criminal trial did not alone violate the defendants’ Sixth Amendment fair trial rights.   By 1990, Steve Brill had figured out a way to try to make money off of serious federal civil trials, and convinced the federal courts to undertake what became - by the time it ended on December 31,1994 - a wildly successful two-plus year pilot program permitting cameras in federal courts.

Then everything stopped.  And our racial past popped back out of its box.

LD: I assume you’re now referring to OJ.

JS: One hundred million Americans learned about and mentally metabolized the crime by watching Simpson and a friend weave through Southern California traffic in a white Ford Bronco.  We watched for hours in eerie quiet, no more certain about whether Simpson would commit suicide than what would happen to race relations.  Later that year, Judge Lance Ito unknowingly altered the course of American constitutional history by ruling that cameras could cover a trial that had already become the first 24/7 reality news show.  On October 3, 1995, thirty-one years after Sullivan, Americans watched at a split screen snapshot of the Simpson verdict, and one that reflected a deep racial divide.

Nineteen years have blinked by.  The internet appeared.   Americans get and discuss their news, movies, books and music in small devices the size of their wallets or handkerchief pockets, which may well be soon be replaced by glasses and contact lenses.  The federal judiciary has so firmly embraced Sullivan that it celebrated its golden anniversary by banning Congress from imposing aggregate limits on campaign contributions - a stunning change from the First Amendment lines as they were drawn circa 1994.  The principle at the heart of that case, we are told, is the Sullivan slogan: The government cannot make choices about what the People say about government when governing itself is at stake, and the federal judiciary exists to prevent government from doing so.

How then is it possible in a nation like this that James Risen is about to go to jail for writing a Pulitzer Prize winning book about CIA incompetence about Iranian nuclear ambitions?  Why do the members of the Supreme Court remain “unbudged in their tracks” - like the Zax made famous by Dr. Seuss - opposed to the People’s technology even as Moore’s law marches us toward quantum computing and nanotechnology?  Can the O.J. Simpson fable really explain why federal appeals courts judges resist “access” to government?  Does it truly come down to a pro-First Amendment court that can’t stand that the People to whom it reports enjoy watching Robert Kardashian’s kids argue with Bruce Jenner?

LD: You seem to feel, with some cause, that the courts are wildly out of touch on the issue of cameras in the courts.

JS: I’ve been trying to understand this mindset for years; I’m still not there.  But I had occasion to re-read Brandeis for work this year.  As I did, it struck me as the closest to theological certainty I’ve ever seen in any branch of government.  The same judges who’ve protected the right to “see, hear and observe” the judiciary have stared back through me at hearings requesting audio-visual access, asking no questions in much the same way that they have resolutely refused to protect a reporter’s newsgathering process.

But this isn’t 15th century Rome, and judges’ certainty that technology leads to evil cannot, as a matter of the physics of intellectual history, be the same as the Pope’s about the printing press.  Federal judges owe their jobs to technology and information.  You can trace a direct line from the Reformation through the scientific revolution to the Enlightenment and directly to the central meaning of the First Amendment.  It mystifies me that a Guttenberg Bible sits in the lobby of the Library of Congress right next door to the Supreme Court; that federal appeals court judges routinely defer to the People’s credibility judgments as a basis to protect Sixth Amendment rights; and that the First Amendment right to attend and report about court proceeding is modeled on the jury system itself.  Yet simultaneously the Court refuses virtually every opportunity to permit the People to “report what transpires” at trials, or in the areas of government of most interest, with the same technology they’ve used for more than a century guided by the freedom of speech cases that this very Court consistently decides.

Every time a jury enters or leaves a courtroom, the judge stands up.  The jury system is the only actual instance I can think of when the People directly do the governing.  I suspect most Americans don’t know that entire courtrooms bow for juries, and I’d bet that fewer would evade jury duty - and understand better their place in the Constitution - if federal courts let cameras enter.  Federal judges need not be afraid that the system will collapse if they allow cameras into courts, or simply if they permit federal trial judges to make their own decisions in each case.   They shouldn’t fear that if they protect reporters with a “qualified right of access,” the world will end.

“Men feared witches and burnt women” is how Brandeis captured the tyranny of theological certainty at colonial trials before the Constitution.  “It is the function of speech to free men from the bondage of irrational fears.”

LD: How have you seen your practice change with new media? With the exception of Edward Snowden, you don’t see many battles over what can be published, since it seems like everything is.

JS: That’s certainly how it’s worked for me.  Today, anyone can publish anything.  Everyone competes with ideas; everyone’s ideas are commodities; the marketplace of ideas metaphor closely resembles the capital markets reality.  So my practice increasingly focuses more on helping individuals and institutions address the integrity of what’s written about them or even the value of their securities.  But what stays the same is the process of finding the truth in any context by managing risk. That’s the common thread of all I do - or that anyone at my firm or any good lawyer does.

In the past year, I’ve helped a range of visible people – an editor, billionaires, public and private companies, a musician, a writer – challenge things that were being written about them that could have been highly damaging or which were written and caused damage.  And it happens in real time.  It’s extremely fast work and involves the threat of serious harm to clients’ reputations.

LD: How do you advise someone who’s facing publication of a bad story?

JS:  At bottom, I tell them that they must – and should - work within the boundaries set by First Amendment case law.   In the last four or five days, I’ve been working with a well-known author who’s facing publication of a false story that, if published, could severely harm the credibility he’s worked for years to achieve.  I try to intuit the core themes of the likely story and advise on the best way to persuade the publisher that the story is false, or just not interesting.

That is not an easy job.

Most nights, after the work is done, I take an hour or two to dictate into my iPhone or MacBook Air, print it, and revise to collect my thoughts for the next day.  As I do so, I find myself re-examining, each night, how First Amendment law is served by - and influences – litigation and public image risk-management strategies and tactics.  That helps us build the record, approach the publisher, and make the next move.  In my 15 years at Boies Schiller, nothing’s been hammered home more intensively than our obligation even before a client signs an engagement letter to imagine its core themes at trial, what its risks are, and what our opponent likely will say in response to those themes and risks.

This morning I was re-reading what I dictated last night about this writer’s problem, imagining when the publisher could ‘go with’ the negative piece, how the timing decision could change the content of what it publishes, and thus whether the publisher could replace the piece with something else, just as newsworthy.  No reporter ever won - and kept - a Pulitzer for publishing a false news report, let alone one they knew was false.

Like many of these kinds of clients, I’ve just met him.  I don’t know him except what I’ve read as a fan of his writing.  The risk is not simply that people will whisper, “he isn’t who we thought he was,” or “he’s a jerk”.  The risk is about protecting the identity he created: for him as for many, his reputation is deeply connected to his creative process and thus who he is and thus his ability to earn a living.

So I try to create uncertainty for the publisher - and any adversary - and control for the client. What tone should we use for the words that communicate our position?  Should they sound like a lawyer’s, or will the adversary be less likely to listen if they do?  Perhaps we mimic the client’s voice for authenticity; if we do, how then to generate a lawyer’s authority?  Many times, in fact, I never surface but use a client’s representative to combine its position and my voice.  That is sexy.  It confuses adversaries because they don’t expect it.  And the confusion creates more risk for them and less for our client.  As the practice grows, I can imagine exponentially increasing uncertainty when an adversary wonders “Uh-oh. Is this the person speaking?  Or those Boies Schiller lawyers who do stuff by not disclosing themselves?”

Good lawyers take control for their clients.  They transfer uncertainty to the other guy, and give their clients peace.  And that’s as good a test as any for an engagement’s success: have we made it easier for our client to sleep at night without offering her an Ambien?  Does she go to sleep without fearing that he’ll wake up to something terrible?

LD: So to protect your First Amendment clients and their reputations, you approach each matter much like your commercial litigation matters?

JS:  Yes.  It might be the particular author I’m working with today, a CEO, even a large institution with a public-image issue - anyone with the risk that they might be sued, or may well want to sue.  They all come to me or my partners concerned that a powerful piece of information will hurt them, or has already done so.

To manage that, I start every matter by dictating the five core truths I would tell a jury were I the client’s adversary - and in cases of threatened articles, what I imagine the worst version of a story itself could say.  I do the same thing imagining my summation for the client.  I do it any chance I get, with my laptop waiting for a plane, with my iPhone driving back from CVS.

Have you read Dan Ariely’s “The (Honest) Truth About Dishonesty?” I downloaded it onto my phone and read part of it in an Uber the other day coming back from a haircut because someone had mentioned it.  I’m traveling to Mongolia soon for work.   I’ve never been there.  But based on my reading and other diligence, I’ll be unknown and virtually unknowable.  How does an unknown lawyer take control?  How does he persuade a resident the other side of his Universe to give him the information he needs to establish that control?  How does he do it when he is the one from the other side of the resident’s Universe?

As I read the Ariely book, I found myself minimizing the Kindle reader and dictating into the Notes App.  My experience has been that most people, rich and poor, are not bad or good.  But they are scared.  And so they make mistakes by miscommunicating.  We all do.  We unintentionally shade the truth, or we lie, or we simply don’t disclose what we need to disclose in order to minimize uncertainty, even to the lawyer who owes us fiduciary duties precisely to help them achieve that goal.  We assume right off the bat that telling the truth makes it more, not less, likely that bad things will happen.  It feels like an economically rational decision; you believe you’ve gained control of a story about you that you like.  And it often works.  That’s why people lie.  It makes them feel confident and free.

But the second they lie - or fail to say things they should say to avoid the appearance that they lied - they have in fact given up control.   They’ve multiplied uncertainty.  And if they get away with it, they do it again and again.

And they do get caught.  The math is pretty easy.  You cannot reduce risk that the truth will hurt you by applying a multiplier to a lie.  If you keep doing that math, your truth quotient drops exponentially.  You started scared; before you know it you are lying; soon you are a liar.

LD: How has that played out, in your experience?

JS: It is the real First Amendment story in modern America.  Journalists and memoirists of all people - the first drafters of history, the Judith Millers and James Freys whose credibility rests on building and maintaining a reputation for truth-telling and creativity - are at greatest risk of being shut down.  Class-action lawyers will now sue for consumers to recover profits of work by journalists accused of being dishonest.  Writers seek out subjects they can characterize at low cost as liars (when those subjects have lied, and when they have not); they trap them; they work with lawyers to write stories marketed to destroy the first movers – from whose mind and heart the whole story first exploded into our cultural experience.  And most of the time, but not always, those second-generation writers believe their stories to be true.  Accounts of fallen heros who lied or simply appear defensive to maintain their identities generate profits twice: for the hero whose prior work zooms up the Amazon charts and the follow-up writers whose profits follow on right behind.

And who is mediating it all?  Lawyers and their advisors.  The first mover gets sued for deceiving consumers.  The lawyer tries to impose a constructive trust on of his Ponzied profits. The court case becomes a third story - with or without cameras.  Instead of managing the litigation risk upfront when they learn someone is investigating them – and there is always litigation risk wherever there is any risk - the first-generation storytellers whose creativity gave them the justifiable belief they could do the impossible make a mistake.  They themselves try to take control.

But first-generation writers (or inventors or businesses) are not experts in managing uncertainty about their own stories, let alone evaluating the litigation risk they pose, let alone predict how a court or jury would interpret them.  I have watched David Boies and Jonathan Schiller up close for 15 years. It is not a coincidence that the high-profile clients with the best bet-the-company outcomes are the ones who listen while those two talk.

LD: What else can your clients do to protect themselves?

JS:  Never stop working hard to make your ideas reality; tell the truth a much as possible no matter how risky it seems; and call my firm when you are afraid to tell the truth, or when you’ve lied or even when someone insignificant says you have lied, even if you haven’t - because we can manage your risk and save you a lot of money and suffering and keep you visible and in the picture.  Yes:  we charge money.  We have to eat, too.  We want success, too.  But very, very rarely do we charge anything close to the amount you will lose by being your own litigator.   If you do choose that path, however, always remember the following default suggestion: start a charitable foundation.

I’m serious.

First, you can turn your ideas into something magical.  The First Amendment gives you that right.  Floyd Abrams made that happen when he won the Pentagon Papers case.  You run the country and have the absolute right to be a “free and fearless” person.

Second, you should try to tell the truth; miscommunicating, to say nothing of lying, creates uncontrollable risk.  Try to be what you imagine Warren Buffet or George Clooney are, not what Lance Armstrong or Ken Lay ended up becoming.  At some point, your idea for a better mousetrap may well become a global behemoth.

Third, you are deluding yourself if you think you are safe simply because you’ve succeeded.  Everyone else is the Sovereign, too. Whether she’s a journalist, a competitor, or a short seller, she will rely on whatever information you’ve left her to use as you became a behemoth.  If she doesn’t lie - or if she has no reason to doubt that you lied – the First Amendment gives her a very good chance of taking away from you the thing you created and building something of her own for her own readers or investors.

Finally, every minute you are focused on taking control is a minute not devoted to making your ideas reality.  So call a lawyer – early – who has a good reputation for managing risk and uncertainty, who can talk and listen simultaneously.  Lawyers are fiduciaries.  That is one of the reasons we must be licensed, and the thing that justifies keeping your communications with us secret.  Good ones use their imagination to envision less risky futures for their clients.  If you give them enough information and listen to what they say, they really can get you out of a jam.

LD: Do you really advocate giving your money away?

JS: Absolutely. If all else fails, give your money away.  I often tell clients and even adversaries the tale of Bill Gates.  Here was a fellow so courageous that he dropped out of Harvard to invent a way of operating a device to sit on your desk like a typewriter but which was as smart as a giant computer.  He was so imaginative, in fact, that sometime around becoming a global behemoth, he realized his operating system would be replaced by the internet; no more need for a desk so no need for a PC and no need for a PC operating system.  Instead of using his knowledge and imagination to build a better mousetrap to navigate the internet, he spent his time controlling his risk, thereby devoting a lot less time to building a great way to sift through the web, but forcing the purchasers of his operating system – 95 percent of all PC operating systems - to use it.

His competitors cried foul because they thought that excluding other browsers from access to Gates’ operating system violated the antitrust laws by making it unfairly expensive to compete. The First Amendment, again, gave way to a statute that punished Gates from using information – actual computer code and marketing instructions.  Someone called my law firm’s  and its founder, David Boies, who worked for the Department of Justice to stop Gates’ antitrust violations

At a videotaped deposition lasting four or so days, Boies made Gates look like a liar because nothing he said was credible.  The founder of the “e-revolution” with a reputation for being an e-genius took hours to agree with David about whether he had sent an e-mail with his name in the “From” field.  He took more hours to answer what he meant in that e-mail by the word “competition” – in an antitrust lawsuit!

Boies showed parts of the tape at the Microsoft trial.  Gates looked so evasive and silly that the judge presiding over it laughed out loud in federal court.  Because the trial took place in a federal courtroom post-O.J., there were no cameras there, but the judge’s laughter was reported by every media outlet from the New York Times to the most obscure bloggers.  And because the First Amendment did require that Gates’ videotaped deposition at some point become public, you can minimize this article right now, go to another window on your phone, and see and hear why Gates’ company ended up stopping the practices that had violated the Sherman Act.

Supreme Court Justices take note: no one watches all four days of Gates’ deposition.  Just the snippets.  Uploaded by citizens to You Tube, some with voiceover commentary, and visual aids.  Not unlike the snippets David Boies played at trial.

In the decades between the moment Gates realized his invention - his idea - would become irrelevant and all of the time he devoted to violating the Sherman Act and resolving those claims, two babies were born on opposite sides of the planet, grew up to spend four full years at the Universities of Michigan and Maryland, met at Stanford and founded a company called Google.  They became billionaires after Google’s IPO, marketed on an idea that, I suspect, came to Gates before either Sergei Brin or Larry Page ever picked up a calculator.

So Gates did a smart thing.  He shrugged his shoulders and became a philanthropist and buddies with Warren Buffet.  Bill Clinton did something similar, putting the question of existence back in the cigar box.   So, too, Michael Milken.  Somewhere along the line, someone advised each that in order to reclaim their identities, they had to appear to be good people, and that the most risk-averse way each could ensure he so appeared was, in fact, to do good.  And although those choices altered their reputations - their identities, their unfolding stories - each choice helped one helluva lot of other less fortunate people.  But only because they gave up some control, and, I’m pretty certain, let experts manage their risk.