This Man Will Likely Sue Donald Trump the Most in the Next Four Years

The civil liberties advocate believes that Donald Trump's cabinet picks "raise enormous concerns"

Anthony Romero.

Anthony Romero. Illustration by Paul Kisselev.

On the wall above Anthony Romero’s desk, the executive director of the American Civil Liberties Union has thumbtacked a tapestry of post cards of Italian Renaissance art. A nobleman poses in a teal silk suit near a portrait of Jesus, which is a few inches and images away from a maiden strumming some sort of ancient lute. Romero, a trim man in a dark gray suit with a burgundy tie and matching pocket square who can rattle off the ACLU’s greatest hits with ease—“challenging Japanese-American internment, to the right to remain silent, the right to a court-appointed attorney if you can’t afford one, the right for interracial couples to marry, the right to contraception, the right for gay couples to marrykeeps more piles of post cards in his desk drawer. It’s a welcome reminder, he explains, “There’s beauty in the world.”

You’ve joked that the ACLU are “like undertakers, we do well in times of plague.” How’s business? Well, business is going to be challenging. Even when you’re an undertaker you lament about the number of bodies that you have to treat. And I fear that the human carnage that’s in front of us, in all seriousness, will be significant.

What’s the most overlooked amendment of the Constitution that gives you solace today? The First Amendment. Without it, the other rights languish. And I think that many people take for granted that the First Amendment rights that we’ve enjoyed have only been in place for the last 100-plus years. Really, the Supreme Court didn’t really uphold the right of freedom of speech, the freedom of assembly, until the early 20th Century. Most folks don’t realize that that was a struggle, often in the courts, to establish the rights of individuals to speak freely and assemble freely. And especially when we look at what the challenges are ahead, the rights of citizens to assemble, to protest, to petition their government are going to be even more important.

What article of the Constitution would you like to rewrite? I tend to think that the Constitution and the Bill of Rights and the founding documents are all evolving. I think ultimately our understanding about living free from discrimination—we’ve come a long way, but there’s still quite a way to go. We still don’t have employment or housing protections for LGBT people in the majority of states across this country. There are still systemic discrimination that plays out that is often hard to challenge in civil rights litigation because you often can’t show the intent.

As a Latino and a gay man, can you recall a time when you’ve personally experienced the restriction of your civil rights? I was lucky that I was sheltered from much discrimination. I had two great parents. But my dad definitely encountered discrimination as a young Hispanic man. He was from Puerto Rico and moved to the Bronx. He wanted to become a waiter at the Warwick Hotel, where he had worked as a janitor, as a houseman, for many years, but he was told that his English wasn’t good enough. But his English was just fine.

And I worked there in college. And I saw that some of the other waiters in the banquet halls—by that time my father had become a banquet waiter, he had filed a union grievance and had gotten the job—but the folks who had been there before him, I knew. They were also immigrants: Greek, Russians, Poles, Germans. Their English often was as good, or as bad, as my dad’s was. And at that time there was always a very kind of a strong, kind of unstated line between the blacks and the Hispanics, who were busboys, dishwashers, bellhops—and white Europeans who were the waiters.

What did you learn bussing tables that serves you today? I bussed; I was a bellhop. I wasn’t very good. You learn to listen. That’s the most important thing. Listen to what your patrons want, listen to what your clients want, as we do today. I think the most important part of being able to be open to different perspectives from all walks of life—certainly working in a midtown hotel I was exposed to people from all over the world, and as a young boy that was kind of a life lesson that continues. I remember those interactions even to this day. Just trying to explain to European patrons that we tip in America, and how do you do that politely? That we don’t get paid quite the way the European waiters get paid and that the tips are expected to be part of the compensation scheme.

Now Trump is everyone’s president. And the oath of office is to uphold the Constitution on behalf of the rights of all here in America and that those laws that are in place have been hard-fought, hard-won, and really are the bedrock of what makes this country work.

Do you expect Donald Trump to undermine civil liberties in this country? And which of his campaign promises should particularly chill Americans? I think we need to take President-elect Trump at his word. And he has been crystal clear in his promises as a candidate and even some of the promises he’s made as president-elect. The promises he’s making on issues like immigration are very troubling. Just the questions that have to concern us, as a nation of immigrants, as a nation of civil rights laws, that we don’t treat people because of their national origin or their skin color or their foreign-born status in an un-American way. And I think many of the policies that he has outlined and continues to outline in terms of the deportation of immigrants raise very serious concerns for us. Immigrants and undocumented immigrants have rights under our Constitution.

Our Constitution is rather clear. Our Founding Fathers in some places they reserved rights to citizens—the right to vote—and other places they reserved the rights to all people: No person shall be denied life, liberty or property without due process of law and we’re all protected by those laws. And so we need to very clear that as President-elect Trump and Attorney General nominee Sen. Jeff Sessions begin to outline what are the priorities for themselves in terms of civil rights enforcement or immigration enforcement that we not trample on some of the basic rights that define us as a nation.

If you were able to speak to President-elect Trump just like you and I are chatting today, what advice would you give him? Not everyone may have voted for him, but now Trump is everyone’s president. And the oath of office is to uphold the Constitution on behalf of the rights of all here in America and that those laws that are in place have been hard-fought, hard-won, and really are the bedrock of what makes this country work.

And I think increasingly troubling has been the series of announcements that President-elect Trump has made in terms of who is going to populate his cabinet. Certainly the records of someone like Jeff Sessions or CIA director nominee Mike Pompeo or Tom Pryce, nominee for Health and Human Services, raise enormous concerns on issues like immigration and civil rights and reproductive rights. It’s a time when we need to understand that what makes America great, using his words, is that we’re a nation of laws.

Do you plan to protest Trump’s inauguration in Washington on January 21? No.

Some critics argue that the ACLU has changed its mission under your tenure. That it was more of an umpire and less about promoting progressive cases. And I was wondering if—would Skokie be something you think you would do today? Sure, we did something very similar with the Westboro Baptist Church. Part of what we must do is defend the rights of everyone, even people we don’t like. Even people we disagree with. And I think it’s essential for this organization, as it always has, to take those moments when the rights of disenfranchised, marginal, even pariah groups are imperiled. And it concerns us as much when they try to shut down a protest of Trump supporters as they do a protest of Black Lives Matter.

Has the ACLU used focus groups to decide what cases to challenge? Never. We use focus groups only to figure out how to talk about the cases we do. But we take our cases because we think they’re the right ones.

President-elect Donald Trump's choice for the Director of the Central Intelligence Agency has alarmed privacy advocates, including the ACLU.
Rep. Mike Pompeo, recently nominated for the top job at the CIA, is seen as a rising star on the Intelligence Committee, but the fourth-term representative also wants to roll back reforms on domestic surveillance programs.
The 58-year-old Republican from Kansas has also butted heads with Muslim-American groups.
The American Civil Liberties Union has already publicly bashed Pompeo for concerns related to civil liberties, privacy, and the due process of law.

When you discussed President Obama’s disappointing record on civil liberties at the Carnegie Council, you fretted, “There isn’t a voting constituency attached to these issues.” Why isn’t there a voting block that cares so much about a free society that they’re willing to vote that way? There isn’t an identified voting block or constituency group for things like drones or military commissions or Guantanamo. The functioning of our democracy, a system of checks and balances, whether the system is fair, whether it works properly, whether there’s proper oversight of the executive branch, seem to be a little more detached in terms of how people think about rights compared to abortion rights or immigrants’ rights or LGBT rights, where there are very specific populations that are directly affected by those policy debates. And so I think one of the biggest problems in the national security context is that no one wakes up and says, “God, what we just did on national security has a direct impact on my life or my rights until it’s too late.”

Have civil libertarians been too complacent about to threats to speech on college campuses? For example, Winthrop University in South Carolina just threatened a student protester for creating an art installation in trees about lynching to draw attention to the fact that a building on campus honors Benjamin Tillman, a pretty brutal governor of the state during Reconstruction. Has your organization been as vocal as it needs to be? Or has it ceded that battle to The Foundation for Individual Rights in Education (FIRE)? No. I’m deeply troubled by what’s playing out on college campuses and universities. I think that both in terms of what’s happening to conservative voices in universities, that are incredibly important for students to be exposed to different points of view. I mean, that’s part of what a college education is all about, especially a liberal arts education. And the idea that we need to be worrying about trigger warnings or microaggressions for adults enrolled in colleges and universities is highly troubling. It’s also true that some of the right-of-center universities have not been protective places for freedom of speech. I think FIRE has somewhat been missing in action when it comes to the work they need to do in conservative universities.

Could you give an example? How does Baylor deal with LGBT groups? How does Jerry Falwell’s Liberty University deal with the rights of women or transgender students? There are problems across the board; it’s not just Oberlin and Berkeley that have problematic policies.

What’s your proudest decision while serving in this job and your most regrettable moment? I’m proudest of the work that we did in the aftermath of 9/11. I was on the job a week, and all hell breaks loose. And it could’ve been a time when we pulled our punches and decided not to be as vigorous or as hard-hitting.

And there were sometimes things that I tripped up over, especially in my early tenure. For instance, there was an effort by the federal government to require all charities of the Combined Federal Campaign [a program to facilitate workplace giving by government employees] to attest that they wouldn’t knowingly hire a terrorist. And I signed that certification. That was a mistake. I signed it at the time because I thought, “Well, I’m not going to hire anyone that I know is a known terrorist. We’ll do our normal screening process. This organization doesn’t hire known terrorists to be on staff.”

But I realized after the fact that many folks felt like I was giving up the ghost. That I was going to subject the screening of our employees to inappropriate screening on terrorist watch lists, which we were never going to do, had never done, had no plans on doing, but I understood that sometimes it’s important to be consistent in all aspects of what we do. Ultimately, we withdrew from that Combined Federal Campaign Program. Now we’re back in it because they changed the rules of engagement. I think what’s remarkable about this organization is that it’s really the secular church for many in America. This is a place where they come and get solace, where they feel part of a bigger calling.

That makes you pope. The gay pope, the openly gay pope? That is both incredibly rewarding, and it’s an enormous privilege, and it’s also an enormous challenge because for many people this is the organization they look to for a fuller articulation of what they want to see right in the world. They want to see change.

This interview has been edited and condensed.

Disclosure: Donald Trump is the father-in-law of Jared Kushner, the publisher of Observer Media.