The Passion of Anthony Romero

This past spring, Anthony Romero, the director of the American Civil Liberties Union, gave a TED Talk at a conference in Vancouver. It had been a few months since Trump was elected, and Romero was there to provide some hope to the audience that things could change. So he turned to one of his passions: Italian Renaissance painters. On a massive screen behind him he projected Ambrogio Lorenzetti's "The Allegory of Good and Bad Government," a series of frescos that depict what can happen when those who rule are held accountable to the masses, and what can happen when they become tyrants.

Romero zoomed in on Lorenzetti's representation of a tyrant. After a laugh line, when he pointed out that the tyrant's hair looks like it takes an inordinate amount of time to coif, he got deadly serious.

"Justice now lies helpless at his feet, shackled," Romero said. "Her scales have been severed. Justice is the key antagonist to the tyrant, and she's been taken out."

In these dark political times, Romero says he likes studying old paintings because they provide context. They show that we have been battling against tyrants, and hoping for good government, for hundreds of years.

Back at the ACLU headquarters in New York, where Romero occupies a corner office overlooking the Statue of Liberty, he's studded the walls with hundreds of Renaissance-painting postcards. More come toppling out of a desk drawer he opens.

We discuss the other reasons he likes the paintings. Well, for one, the works are often homoerotic, and Romero is, in his words, "totally, 100% gay. Ten on the gay scale." But more important, Romero seems to appreciate how the painters play with power. He hands me an Agnolo Bronzino painting, a simple depiction of a young aristocrat. The image is almost boring, but the man's codpiece is massive, and so the painting almost becomes parody.

"He's doing it to twist them," Romero says. "To show how ridiculous these self-important people are."

The ACLU is known for its work on free speech, on gay and civil rights, but if it had an overarching mission under Romero, who has been there since 2001, it would be in line with these paintings: to expose and challenge the powerful, even as Romero works with them day in and day out--to prove that no one, not even a president, and not even people Romero likes personally, is above reproach.

It's both a philosophical strategy and a practical one: The organization has to play this role because of its size, operating more as a thorn in the side of the powerful than a sufficient bulwark against their tyranny. Even though the ACLU has quadrupled since the election, growing from 400,000 members to 1.6 million, it's still only made up of about 300 lawyers. Romero estimates Trump has about 19,000 lawyers working for him between the Department of Justice, the FBI, the Department of Labor, and every other agency now under his control. It's David vs. Goliath, but in this case Goliath loses a lot more.

Romero came on as executive director just a few days before 9/11, and he learned early on that he had to choose his battles. He has three criteria for taking on any legal battle: Is the issue important? Can the ACLU come up with a strategy for winning? And would the ACLU add anything unique to the battle--i.e., are there already good organizations working on it?

Campaign finance reform? Important, but Romero says he can't really figure out how the ACLU would help at this point. Ending employment discrimination based on sexual orientation and gender identity? The ACLU state offices contribute resources when they can, but the Human Rights Campaign already has lawyers on the issue. Same with Planned Parenthood and abortion rights, which have their legal advocates. The ACLU will lend its voice, but it doesn't have the capacity to add much more.

But choosing battles has gotten harder under Trump.

"When you look at all these issues--immigrants' rights, reproductive rights, civil rights, LGBT rights--you're talking about massive changes to the nation's laws and policies that will have a direct impact on how millions of Americans live their lives," Romero says. "A big part of our effort is going to be just holding off the worst of these abuses."

I asked James Esseks, the head of the organization's LGBT and HIV project, who arrived at the organization shortly before Romero, if there are any moments that stand out in Romero's leadership--any outbursts of emotion, any yelling at a Trump supporter during a meeting. No, Esseks replied. He's a tactician, and an effective one. "He has his hands in a lot of different issues, and he gets things done," Esseks said. "For the organization and for the country."

Romero's reserve--some might describe it as coldness (beyond the Renaissance postcards, there's barely anything in his office--just a few wilting plants)--might come from a position of recognizing his privilege.

He grew up in the Bronx, the child of Puerto Rican immigrants. He's been called a fag too many times to count, and still gets called one sometimes. But his job and his life are good, and so when he gets called a fag nowadays, he either says "fuck you" or just keeps
on walking.

The real heroes, according to Romero, are the people the ACLU represents, like Gavin Grimm, the transgender teen who sued his Virginia school district for barring him and others from using the appropriate bathroom for their gender, and Edie Windsor, the woman at the center of the Supreme Court's decision to overturn the Defense of Marriage Act.

"They are putting themselves on the line and staking their own reputation, dealing with public scrutiny and the vitriol that will come with that to make a change," he says. "That's incredible."

Romero's tenure at the ACLU hasn't been without controversy. Most recently the organization felt some backlash when it undertook a PR campaign to defend transphobic and anti-immigrant firebrands Milo Yiannopoulos and Ann Coulter, both of whom had their planned speaking engagements at UC Berkeley canceled after protests. Sure, Yiannopoulos and Coulter are not heroes like Grimm and Windsor, Romero says. And yes, canceling a talk at a university is not an infringement on free speech in a legal sense. But, for Romero, it's not all about morally clear legal wins.

"I'm not as worried about America becoming a place of censorship as I am about America becoming a place where we begin to accept restrictions on or self-impose limitations on freedom of speech," he says. "I want to make sure speech remains as messy and as loud as possible."

His defense of Yiannopoulos calls to mind the Bronzino postcard he keeps in his desk drawer. Romero is saying that those in power, even the ones he agrees with--the administrators at Berkeley, the liberals who detest Yiannopoulos and Coulter--still need to be reminded of their fallibility.