San Francisco Has Beat Trump Executive Orders Before. It’s Ready to Fight Back Now.

When a vast coalition of progressives challenged the Trump administration’s major executive actions eight years ago, the office of San Francisco’s city attorney stood out among the crowd for punching far above its weight. It was the first to sue Donald Trump over his withdrawal of federal funds from sanctuary cities, ultimately winning the case on appeal.

This time around, City Attorney David Chiu is bracing for a flood of Day One executive orders — many of which he plans to immediately challenge in court. He’s even tasked one of his deputies to lead the effort: Mollie Lee, a former American Civil Liberties Union lawyer who was senior counsel for the Kamala Harris campaign.

“All of us are gearing up for what we anticipate will be an attack on our cities and counties,” he told NOTUS in an interview Friday. “Offices like mine will react as quickly as we need to.”

Trump is expected to target undocumented immigrants by stepping up deportations and further erode measures that protect gay and transgender individuals. Chiu said he’s preparing for all of it.

Chiu said one particular concern is Trump’s vow to attack birthright citizenship, which is enshrined in the 14th Amendment to the U.S. Constitution and states that “all persons born or naturalized in the United States, and subject to the jurisdiction thereof, are citizens of the United States.” In May 2023, the Trump presidential campaign released a video in which Trump said he would sign a “Day One” executive order to undermine the amendment that’s been in place since 1868. In the video, Trump complained that “the United States is among the only countries in the world that says even if neither parent is a citizen or even lawfully in the country, their future children are automatic citizens the moment the parents trespass onto our soil.”

Chiu, who was born in Cincinnati to Taiwanese parents, told NOTUS, “This is personal for me.”

“I am the eldest child of immigrants. I believe in the promise that anyone from any corner of the world can build a life here. This is settled law grounded in the 14th Amendment and endorsed by the Supreme Court in the 1800s,” he said, noting that the very case that finalized the matter stemmed from United States v. Wong Kim Ark, a Chinese American man born in San Francisco.

Chiu said any attempt to strip people of citizenship “would be devastating for our economy, for families, for the social fabric of our city, our state and our country.”

Any legal resistance in San Francisco will be backed by a newly created Civil Prosecutors Coalition, which is less than a year old and includes city and county attorney offices in Los Angeles, Oakland, Santa Clara, San Diego and San Jose.

Tony LoPresti, county counsel in Santa Clara, told NOTUS that “a huge number” of the 110 lawyers in his office will be monitoring Trump’s first moments in office and sketching out legal challenges that will get funneled to the 15-person team “devoted to social justice and impact litigation policy.”

“We filed seven lawsuits last time to defend the county’s ability to take care of its residents, and we’re going to be ready to file those lawsuits again,” LoPresti said.

Trump’s anticipated crackdown on migrants is at the forefront of LoPresti’s mind, particularly any executive orders that aim to limit government assistance to those the Trump administration considers unqualified to receive it.

“We’re aware that the administration plans to be aggressive around immigration policy,” he said. “We have the second largest public health care system in the state, just purchased a fourth hospital and serve our most vulnerable, poorest population. Any challenges to our ability to carry out health care services would be top of mind for us.”

Small city and county offices aren’t alone. Democratic attorneys general across the country are already teaming up, as Bloomberg reported on Friday, noting how more than a dozen are currently trying to throw their support behind a Biden administration measure that ensures immigrants who entered the country as kids can still get access to Obamacare — one that’s being challenged in North Dakota federal court.

Special interest groups are also preparing to enter the fray. The Lambda Legal Defense and Education Fund, which advocates for gay and transgender communities, was able to hold back several of the first Trump administration’s policies — including its “Death to Asylum” rule that would gut protections for people fleeing persecution and torture. There are still 12 countries where same-sex sexual contact is still punishable by death, according to the Death Penalty Information Center. Lambda said it’s prepared to quickly spin up its legal challenges once more.

“Based on past patterns, it’s a safe bet that similar attacks could be on the horizon,” Jose Abrigo, Lambda Legal’s senior attorney, told NOTUS by email. “Rest assured, attacks on our communities will not go unanswered.”

However, it could be up to smaller government offices that are already dealing with mundane municipal affairs — like Chiu’s in San Francisco — to challenge certain legal issues that touch on the use of taxpayer funds and incursions into local jurisdictions.

On the phone Friday, Chiu’s tone shifted when he spoke about Trump’s vow to turn the nation’s military on the U.S. civilian population and use it to bolster federal law enforcement.

“We’re on the lookout for attempts at mass deportations and the new use of different arms of the federal government, including the military, to enforce immigration law,” Chiu said. “We’re all highly concerned about what could happen.”

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Jose Pagliery is a reporter at NOTUS.