Ted Boutrous on the Trump Admin, the First Amendment, And Why Now Is Such an Exciting Time for Journalism

The Control Room - Conversations for Growing Companies


Weeks before the 2016 Presidential election, Gibson Dunn’s co-head of litigation (and fellow USD Law grad), Ted Boutrous, took this unusually public Twitter stance against a major party nominee. We knew then that this was no ordinary nominee, and we saw unusually public stances coming from many places. Even so, a well-respected Big Law leader making this declaration drew attention from lawyers and non-lawyers alike all over the country. I reached out to Ted in November to find time to talk. I wanted the story behind this tweet and I wanted to learn what happened behind the scenes in the weeks that followed.

But since November, more has happened than most of us could have imagined. We’ve seen rapid changes in what free speech means and how it’s treated – from the government’s outright hostility toward journalism, to upending established norms in how the government and the press co-exist, to the administration’s communication with the public, to putting into question the basic assumption that what the President says is true.

Ted is deeply involved with each of these issues. In this interview, he explains how he got where he is and what he’s thinking about now. We talk about Twitter and the First Amendment. And we explore what you can do now if you care about journalism.

[Find more from Ted on Twitter at @BoutrousTed. Listen to the interview on JD Supra or download from iTunes.]


Josh: We'll talk in a few minutes about your now famous tweet where you said you would defend anyone sued by Trump for exercising their free speech rights. I want to talk a little bit about you and your practice first. I learned of you through your First Amendment work. But you actually do an awful lot more than that. Could you lay the groundwork about what you do and who you work with?

Ted: I went to law school at the University of San Diego, and wanted to practice appellate constitutional law, I really wanted to be at the intersection of government, the Constitution, but be in private practice. 

When I joined Gibson Dunn, my law firm, we had just started an appellate group in Washington, D.C. Ted Olson, who went on to become a Solicitor-General had come back from the Justice Department back in the mid ‘80s and started an appellate constitutional law group, and I thought that sounded like exactly what I wanted to do. I was one of our first associates in that group. This was in 1987. And that practice really blossomed and in some ways exploded. 

It is much broader than even appellate litigation. It allowed me to get involved in thorny, complicated, interesting, high profile issues that cut across a whole range of topics, sometimes for corporate clients, sometimes for individuals. 

I was a staunch Democrat coming out of law school and one of my first projects was to work with Ted Olson representing President Reagan during the Iran Contra investigation. 

I was a staunch Democrat coming out of law school and one of my first projects was to work with Ted Olson representing President Reagan during the Iran Contra investigation. So it was very easy to make the switch when you’re representing a client. But it’s been a great, great practice for me, and a great opportunity. As part of that I began working on First Amendment matters.

Josh: When you say you wanted to practice appellate constitutional law, isn't that every law student?

Ted: It is. I got lucky. I took a somewhat unconventional path when I dropped out of college twice. I didn’t quite know what I wanted to do. I started out in North Dakota where I grew up, and I realized it’s too cold there. I’m getting out. So I left college there, had the bright idea of going to Arizona, which was fantastic. When I was there, I took a philosophy of law class and found that's what I wanted to do. My dad was a lawyer, so I’d always thought about it. 

I didn’t know the limitations that might be out there on exactly the issue you mentioned. A lot of people want to do that kind of work. I didn’t want to clerk because I had taken a couple of extra years to get through law school. And I thought, this is what I want to do, this is a great law firm, I’m going to go do it. It’s a bit of a testament to, don’t think that there are limits on what you can do. 

...where you come from and how you get there doesn’t limit your ultimate destination. 

I think it’s one of the things that’s great about our country, that where you come from and how you get there doesn’t limit your ultimate destination. So I got lucky. I found a firm I loved immediately. Ted Olson and I bonded very quickly and worked together for years, even though he is a conservative Republican and I’m a liberal Democrat, but somewhat non-partisan. It was sort of a series of lucky breaks and it’s been a great place for me and I love what I do. That makes a big difference too.

Josh: What was it about a philosophy of law class that did it for you?

Ted: It was a class that focused on Ronald Dworkin, probably one of the greatest legal philosophers of all time, and his method of legal philosophy and thought. The high level of analysis and how legal thought and legal issues intersected with basically every aspect of society. So public safety, product development, the Constitution, the separation of powers, technology, business. 

Everything intersects with the law, and it really gelled for me, that being a lawyer would allow me to think about the kind of things and do the kind of things that I really like to do. I’ve always been very interested in politics and I was a political science major. Being able to have both a job that pays money but also lets you participate in these broader issues in society, that’s what hooked me.

Josh: You mentioned you dropped out of college twice. Then you ended up graduating at the top of your class at USD. What clicked? Did something change?

Ted: One, I realized that, I knew what I wanted to do when I was at Arizona State. I wanted to go to law school. I decided at the last minute before law school admissions would kick in. Then I ended up going to a law school I absolutely loved. It was like heaven. I think you know it well. 

Josh: I do. Our stories are actually very similar. I took the LSAT on the last day of late registration, or signed up for it on the last day of late registration and said, I think this is what I want to do. And then ended up going to USD, from Colorado State University. Very interesting parallels here, actually.

Ted: That sounds very familiar. I ended up at this great place, where it’s a beautiful place to be, and I plunged in to law school. It was like something clicked. I was on a new path and I knew what I wanted to do. I also met my wife on the first day of law school, so that helped. That gave another mission to my life and career. 

I think you go through phases, and as part of the journey, you learn a lot and you end up finding out what you really like to do. If it turns out that it’s a profession that you can survive on, it is a nice combination.

Josh: Sure. So then you're working with Ted Olson, kind of an amazing place to fall into as that practice is growing. You're now one the preeminent people who does what you do in the country. Were there a couple of milestones as you were progressing in your career at Gibson that you felt like, you'd reached either a new level or that you'd really done something that you were proud of?

Ted: Yeah, you know, it’s interesting because my law firm is a great place because we create a lot of freedom for even the most junior associates when they walk in the door. The minute I walked in the firm, I felt like I was an independent operator but I had this great support network and great mentors and all the things you’d look for. A lot of independence. 

...my law firm is a great place because we create a lot of freedom for even the most junior associates when they walk in the door.

One of the first things that made me think I was breaking out a bit was, I wrote an op-ed piece for the Wall Street Journal on the independent counsel statute, which at the time, this was the early ‘90s, was very controversial. It was published, and it was a big moment for me. I’ve since probably written 25 of them for the Wall Street Journal. But the fact that I had partners who wanted to let me be out in front, I think is a lesson in giving your more junior colleagues responsibility and opportunity and the ability to try. When you’re just starting out, it makes a huge difference. 

My practice was starting to thrive independently once I became a partner in the mid ‘90s. Then the guy who’s now the chairman of our firm said, you really should think about coming to Los Angeles. You could build a west coast version of the appellate group and I thought that sounded great. My wife Helen and I had always thought about coming back to California. We fell in love with Washington D.C. life but we jumped at the chance to move back to California. 

When I came out to California, it was like a whole new world because you've got a lot of litigation, number one, but with the technology boom, you had vibrant commercial activity. That opened up a whole new world for me. Another launching pad for me was, you meet good clients. When Walmart had this massive class action certified against it, I had never represented Walmart. I was one of the people they talked to. They hired me back in 2004 to help them on the appeal, and I ultimately became lead counsel on the appeal. That went all the way to the Supreme Court and we were able to get that class certification overturned. And it was a landmark decision. So a series of those sorts of things. 

This goes to the mentors and lucky breaks. Bob Sack, who ultimately became a judge on the Second Circuit there in New York was one of our partners in the New York office and a legend in the First Amendment area. He asked me to help him on a First Amendment case that was actually a Senate investigation regarding who leaked the Anita Hill allegations about Clarence Thomas to the media and to our client, Tim Phelps, who was at Newsday. That was my first big First Amendment battle. We asked the Senate to recognize a reporter’s privilege basically. And they did that. It was a wild experience. That added this First Amendment journalism piece to my practice that I think created the world that I’m now in. Those are some of the milestones for me that got me where I am.

Josh: Why do you think you were asked to help on that First Amendment case?

Ted: It’s interesting. It was focused in Washington, which is where I was at the time. I was one of the junior to mid level associates. Ted Olson was going to get involved as well. We're very good at collaborating across practice groups and offices, so Bob called Ted and Ted suggested I help, and Bob and I became very close colleagues and worked together over and over again on really significant, interesting, major First Amendment battles for the Wall Street Journal, the New York Times, all the networks. When you look back, I think I had a series of lucky breaks, being at the right place at the right time, and also being at a place where you have collaboration and everyone looking around to find who can play a role that will make the team the strongest. Those things really benefitted me.

...it drives me crazy when President Trump says these false things about journalism and about journalists, because I think it’s a crucial part of our democracy and our society.

Josh: So you're talking here your first case in defending journalism. And as you mentioned, that's become a pretty significant part of your practice. I saw an interview that you gave a few years ago where you actually said if you weren't a lawyer you would have been a journalist. Do you still believe that and if so, why?

Ted: I do. I’m a big consumer of news and journalism. It’s one of the reasons I wanted to go to Washington out of law school. It’s one of the things that I really thrive on. I have a lot of respect for what journalists do. That’s why it drives me crazy when President Trump says these false things about journalism and about journalists, because I think it’s a crucial part of our democracy and our society. 

I love journalism, and representing journalists, I got to see up close and personal what they do, what’s important to what they do. And I like to write, and sometimes people forget that as lawyers, you do a lot of writing. A journalist once said to me, lawyers are probably the highest paid writers in the world. There may be some screenwriters and the like and novelists that outpace us. But it’s a luxury as a lawyer to be able to write and I like to write. 

Journalists, one way or another, whatever type of journalism they practice, they have to write and synthesize information and determine what’s important, and it has a lot in common with what lawyers do. Ask, interrogate people, look for evidence, put it all together, make the case if you’re an investigative journalist. There are a lot of things in common, and working closely with news organizations and journalists made me think even more highly of what they do and that that would be something that I’d want to do.

...probably the best journalists in the world exist right now

Josh: What do you make of sort of the current state of journalism?

Ted: I think that it’s a really exciting time for journalism and that probably the best journalists in the world exist right now, that have ever been on the face of the earth. 

Josh: Anyone you want to mention?

Ted: I don’t want to single anyone out because I’d be leaving someone out. But if you look at the reporting that has been done during this campaign, if you look at the story that David Sanger did in the New York Times on North Korea a couple of weeks ago, the New Yorker piece on Russia that was a couple of weeks ago. It is such strong journalism. It’s powerful work. 

As a lawyer, I would see journalists from practicing. When I'm not representing a journalist, I would see journalists from the other side covering me. I got to know Linda Deutsch who is now retired from the Associated Press. Watching her in action, she’s probably the greatest trial reporter. She covered the Manson trial, the OJ Simpson trial, that’s where I got to know her when I was representing journalists there. To see how she could observe and then write it down with accuracy and making it interesting and exciting, and doing it instantaneously, right there, here’s what happened, and to capture what people said, I think we’ve got journalists that are doing tremendous work. 

...it's a great time for journalism and the fact that we are in this atmosphere where we have, everyday, about a year’s worth of news with President Trump and his administration, I think it’s going to keep going.

There are some that are not, and that’s one of the things that we confront here, the blending together of organizations that on their face purport to be journalistic enterprises who are not following the conventions of journalism. It can get a little bit complicated. But if you really look at the organizations, and it’s not just what we’ll call traditional media; you’ve got Buzzfeed and others just doing tremendous work, like Politico. The list goes on and on. So I think it’s really a great time for journalism and the fact that we are in this atmosphere where we have, everyday, about a year’s worth of news with President Trump and his administration, I think it’s going to keep going.

Josh: I think it's pretty amazing to see what's been going on. You mentioned the blending of organizations that purport to be journalistic and that aren't. And we've seen over the last several months lots of different story lines around the difficulty that exists and may continue to exist, and understanding what's true, right? How do you see that from where you sit on the inside of some of these conversations?

Ted: It is something I’ve thought about a lot because we have a president who says things that everybody knows is false and are false. The tweet about President Obama supposedly wiring Trump Tower. Everybody knows that’s false. And yet he claims it’s true. His apparatus claims it’s true. He has a media platform of his own. He said last night I think with Tucker Carlson that, he thinks without Twitter he might not have gotten elected and it really is his megaphone. So you’ve got that piece of it. 

Then you have the fact that he relied on this blend of information for coming up with his tweet that included a story in Breitbart which falls in my view into the category of organizations that act like they’re news organizations but they really aren’t. They are information producers. I’m not saying they shouldn’t do what they do, but it’s not what I think of as journalism. And they’re relying on a Mark Levine radio diatribe and all that is sort of mixed together and they’re spewing out information that’s not true and they’re jumping to conclusions. 

...one of the things that is used as a mechanism to exert power over the people is to confuse the facts and to say up is down and down is up. 

I think that’s one of the dangers that we face right now and there’s been a lot of writing and discussion about how in authoritarian regimes and totalitarian regimes, one of the things that is used as a mechanism to exert power over the people is to confuse the facts and to say up is down and down is up. That’s why journalism is so important right now, that true reporting, sticking with the facts, digging for the facts, don’t stop focusing on a topic just because there’s another topic that’s come along, I think is so important. Because that’s what gets lost when we talk about the First Amendment: one of the main purposes of the First Amendment is to make sure that citizens have the information they need to make sensible decisions about how to govern themselves. If you use that premise, that is a crucial mechanism that we need the journalist community to help us achieve. I think that getting to the truth has never been more important than it is right now and journalism is essential to that. And lawyers as well. I always come back to the relationship between what lawyers do and what journalists do. They are two of very few professions that are embedded in some way into our constitutional structure and are part of what we think of as the fabric of our democratic system.

Josh: So you mentioned the fabric of our democratic system and you also mentioned Twitter.

Ted: Ha. Yes.

Josh: Let's talk about Twitter in the context of the discourse. How did you phrase it? People who make intelligent decisions around how they are governed. You've been a Twitter power user for a long time, long before this election cycle. How does something like this fit into the broader conversation of the exchange of ideas that we think about broadly with the First Amendment?

Ted: I think of Twitter in several ways. First, I really started using Twitter as part of an information delivery system and for some of my clients, where they were involved in big cases and the folks on the other side were using Twitter and all sorts of other mechanisms to get their message out. I’m a big believer where it is appropriate to engage with journalists and to speak to the public about a case where there are public policy issues in particular, but especially if your opponent is coming at you and using Twitter and Facebook and other platforms to make their case and to try to win and defeat you both publicly and in the case. That’s how I started on Twitter. 

Then my eyes were opened in terms of the information delivery system that it is and as you know, journalists in particular thrive on Twitter, use it a lot and in terms of getting basic news about what’s happening in the world, you can create your own universe, but if you just focus on major journalists and news organizations of all different types, it’s heaven in terms of getting information. So that’s two prongs. 

Then you have the falsity and the downside of unlimited free speech. You have people saying awful things on Twitter, false things on Twitter. You have the President of the United States and then the presidential candidate before that, same guy, Donald Trump, saying false things, threatening people, going after individual citizens, accusing his predecessor of what would be the crime of the century. Those are some of the downsides. But another premise of the First Amendment is, the truth will out. That if you keep battling back and forth for information, the truth will survive. And you can fight falsity with truth. I don’t think that that’s changed. It’s just more of a free for all. 

...one of the main purposes of the First Amendment is to make sure that citizens have the information they need to make sensible decisions about how to govern themselves.

We need to keep all those features in mind when we think about Twitter. On the tweet heard around the world as you called it, at least from a lawyer’s perspective, then-candidate Trump at Gettysburg had used that platform to denounce the many women who had made accusations of sexual misconduct against him. Then he declared that he was going to sue them all once the election was over. That struck me as such an outrageous thing for a candidate to do, to threaten, to intimidate citizens from speaking out during a presidential election, it never happened before. 

I popped down to Twitter and said I'd represent anybody pro bono, who Trump sued for exercising their First Amendment rights and the response was amazing. I had legendary law professors like Laurence Tribe saying I’ll help, and people all over the country, lawyers saying, we'll help if you need us. It was just amazing. And that could never have happened without a platform like Twitter. We organized a little team and some of us started working together on various matters now, and so it actually had this amazing effect. Platforms like that have many amazing, positive features.

Josh: Let's actually talk a little bit about what's going through your mind when you decided to tweet that. You were reading an article or you saw a clip and you pull out your iPhone and you banged that out real fast and throw it out to the world and then 50,000 people or something respond to you, or what happens there?

Ted: It was interesting. I think that was October 22nd, a couple of weeks earlier, when President or candidate Trump threatened to sue the New York Times, Melania Trump had threatened to sue People Magazine, they were saying they were going to sue New York Times for publishing that state tax return information and for libel. I thought, this is crazy. And the Palm Beach Post had come out with its first piece. 

I think someone prompted me and said, these smaller news organizations people, they’re not going to be able to afford defenses. So I said, hey, I'd represent them pro bono. That got a very strong response on Twitter, especially because we lawyers don’t get the Donald Trump or George Takai treatment from Twitter. When I was actually watching Trump’s speech live at Gettysburg, I thought, this is crazy. I talked to my wife and we were just marveling at it. Then someone retweeted my original tweet and said, gee, this might be a good time for people to know that your vow still stands. I then conferred with my wife Helen before pushing the button and said, I repeat, I will represent anybody who is sued or threatened by Trump for exercising their First Amendment rights, and sent it off and it just exploded. 

I went to sleep, it was a stream of activity, and then the things that happened overnight were, in terms of retweets, replies, it was wild to see. I’ve represented people who were part of that group that he was threatening that day and related to those issues. I felt that had an effect. It also helped create this network of lawyers who are standing by on First Amendment issues, immigration issues, constitutional issues that are no doubt are going to keep arising. So it was quite an interesting experience.

We have a firm where being politically active and having a pro bono practice is encouraged...

Josh: I think it's interesting and it's wise that you asked your wife. I notice you didn't say you actually asked anyone at the firm. But I guess maybe you don't need to.

Ted: Well, I’m now senior enough, I'm on a management committee. I had a pretty wide leeway. But I did check in and make sure folks knew about it. We have a firm where being politically active and having a pro bono practice is encouraged; this was a little more unusual. So I did go back and explain and give everybody a heads up. But I think First Amendment issues are a truly non-partisan issue. The First Amendment is neutral, and that’s why I thought, in a campaign, come on, you can’t use the power of your position to try to intimidate citizens, voters from speaking and participating in a political battle. So I felt I was on very safe ground. But as a lawyer you've put your finger on some of the risks that we as lawyers have on Twitter too. Especially with client matters, you do need to keep all those issues in mind.

Josh: You mentioned a couple of other things there. Specifically, that this group has been building a coalition, I think some of it's been pretty public, Laurence Tribe you mentioned, has been very vocal, and some others. Is there some collective activity going on behind the scenes where you’re all are talking to each other?

Ted: Well, it’s been I think very healthy for the legal profession just like I think Donald Trump has been healthy for journalism in a strange way because lawyers at big law firms and professors and lawyers at small law firms, plaintiffs lawyers, defense lawyers who agree on legal principles and policy principles are communicating about these issues around the country. 

For example on the immigration side, I’m working with Professor Tribe and Professor Chemerinsky from California here on the first DACA case, the immigration case that we’re handling. That grew out of communications we had back in the campaign. And you've seen law firms in the immigration band, battle, we filed the brief in the Darweesh case there in the Second Circuit. There were terrific briefs filed in Hawaii and in the other cases. You've seen the legal profession step up in a big way here. 

Different people have different views on policies. I agree with a lot of Republican policies, particularly business-oriented policies, but this president has been very clear that he's pushing the envelope on constitutional issues, on legal questions. The travel ban, they're peddling to the middle. On the immigration front, as you know, for businesses, the tech industry in particular, but many other businesses think that we are the leaders from an economic standpoint because we welcome people from other countries. It's who we are as a country. It's a galvanizing thing from a legal perspective and we're seeing it. 

I am spending so much more time talking to my colleagues at different firms, at public interest groups, at law schools. It's very exciting and energizing. I feel good about the country because of the way people are responding. We can all disagree with policies, we can disagree with the approach that the administration takes, or agree with it, but there's a place for lawyers that I think we haven't seen in the democratic process at this level right now that is really remarkable.

Josh: Does it feel different to you be a lawyer now than three, four, five months ago?

Ted: It does. You've put your finger on it. I think it took my own consciousness to another level, where my own practice as it was before, it's always had different elements and my cases ranged widely, go from defending against the class action, arguing an appeal, arguing a case on a big punitive damage order or something like that, and then First Amendment issues and the like. 

It's a legal awakening and another level of consciousness of how important the rule of law is...

But it's a legal awakening and another level of consciousness of how important the rule of law is, how important lawyers taking responsibility for protecting the rule of law is in our system. I do feel differently and it's a positive thing, although there are ups and downs when one looks at what is happening in the world. I think your question is a good one because the answer is absolutely yes, I feel differently as a lawyer, and feel I and everyone else has even more responsibility to play a role in ensuring that our system functions properly.

Josh: Two more questions. One, everyone should feel responsible to make sure our system's functioning properly. What can people actually do right now? Lawyers and non-lawyers, maybe let's split it up. What would you tell people if they are concerned about, even if we just leave it at First Amendment issues and things that you said maybe shouldn't even be partisan, the functioning of the democracy. What are things that you feel people should be doing or could be doing right now?

Ted: I think there are several things. One, participating in the process in an orderly way. The protests that you've seen, the women's march, other protests, that's democracy. I think getting involved with issues, it sounds a bit trite, but it's absolutely true. It makes a huge difference. I think on both sides of the aisle, standing up for principle. You look at the Republicans, you can tell they're uncomfortable with some of the things that President Trump is doing and saying. And some of them are pushing back a bit. But be they Democrat or Republican, stick to principles, stick to what you believe in and protect and get involved in things where you can protect those values. 

On the First Amendment front, supporting the Reporter's Committee for Freedom of the Press, organizations like that. I've been on the board of the International Women's Media Foundation for many years, that seeks to protect women journalists around the world. Usually we were focusing more on foreign countries, because they didn't have the First Amendment protections. But now you see that we need protection of journalists in the United States in a way that we didn't before. I think you've seen a renaissance for the ACLU, Public Council, other organizations like that, where people are saying, wow, those groups really can make a difference. I think supporting those groups, putting pressure on your elected representatives, these town hall meetings. All of a sudden people realize, wait, I could go to a town hall meeting even if the person in office is someone I didn't vote for. I get to go talk to that person. It doesn't have to be angry. It can be a dialogue. So I see there's an awakening around the country and on both sides, across the political spectrum. That's a real positive thing. We have President Trump to thank for that, and we'll see how it all plays out.

Josh: You said that the First Amendment isn't partisan. You said there are some folks that are uncomfortable with some of the things that are being said and the way that information's being conveyed right now from the administration. Are you concerned that the First Amendment may become partisan or that people will not defend it in the way that maybe you believe it should be defended, in this environment?

I am concerned that the approach that President Trump and his team is taking is meant to devalue and undermine and damage the First Amendment and free and open dialogue in the country

Ted: I am concerned that the approach that President Trump and his team is taking is meant to devalue and undermine and damage the First Amendment and free and open dialogue in the country. To say that journalism and journalists are the enemy of the people, for example, that is wrong. That is flatly contrary to our constitutional principles. 

I'm not concerned that the journalists and others who fight for First Amendment freedom and who engage in journalistic activity and speech in a way that's meant to participate in the democratic process are going to hold back. That's one of the things I feel very strongly about. 

You see in other countries that, Russia for example, which appears to be a template in some ways for our current administration, killing journalists, squelching journalism, is a means towards more power. I don't think that's going to work in the United States. I don't mean to suggest that the killing part was even contemplated. But I do think that this delegitimization of journalism, this denigration of the whole process, this ridiculous fake news label that the president and others are using. That's meant to change how we look at the First Amendment. The good news is, I don't think it's going to work and I think journalists are being inspired to do an even better job, that is going to be essential over the next few years.


Download the interview from iTunes.

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