Less than 24 hours after President Donald Trump signed an executive order to significantly restrict birthright citizenship last week, nearly two dozen state attorneys general filed lawsuits seeking to block the order. Two days after that, a federal judge in Seattle issued a two-week pause on the measure as the court considers a more extensive hold on the policy.

This week, another federal judge temporarily blocked the administration’s attempt to freeze federal assistance and loans. This came after another joint lawsuit with 22 state attorneys general and the District of Columbia challenged the move.

This swift legal action from some of the country’s top law enforcement officials was months in the making, former Oregon Attorney General Ellen Rosenblum told The 19th.

“We saw this coming, even though we hoped it wouldn’t. We started preparing as the Democratic AGs almost two years ago for the potential eventuality,” Rosenblum said in an interview days after Trump’s inauguration. “I believe that there’s no group better prepared to push back where appropriate.”

Rosenblum entered office as Oregon’s first woman attorney general in 2012 and served during three presidential administrations before stepping away in December 2024. In her position, she oversaw an office of more than 350 lawyers who challenged the first Trump administration hundreds of times on things from executive orders to federal rule changes. 

She was part of a group of Democratic attorneys general who sued the administration over its travel ban on several majority-Muslim countries and its attempt to end the Deferred Action for Childhood Arrivals (DACA) program that protects certain undocumented people brought to the United States as children.

Rosenblum explained that before suing, a state attorney general’s office staff must evaluate whether a specific policy will be harmful to people in her state, assemble a legal team that consults with other state attorney general offices to decide what cases to sign onto and divide responsibilities as well as determine which courts would be the most appropriate to file a legal complaint. As the team builds its case, it also gathers personal testimony from people who have been directly affected by the policies.

Rosenblum noted that last week’s challenges to Trump’s birthright citizenship order — brought by her successor in Oregon and more than 20 other state attorneys general — were filed in two states, Massachusetts and Washington state.

“Sometimes it makes sense to have multiple actions sort of paralleling each other,” Rosenblum said. “What you do as lawyers is you take a look at what potential claims can be brought, and then you decide which ones are going to be most likely to be successful. You don’t necessarily want to throw all the mud on the ball. You want to pick and choose.”

A lot has changed since Trump first sat in the Oval Office eight years ago, she added.

“We didn’t know what he was going to do, and we didn’t really know a whole lot about how to push back,” Rosenblum said of Trump’s first term. 

At the time, Trump lost a number of legal challenges because of executive actions that were rushed, “frivolous” and “over the top,” according to Rosenblum. A federal district court judge said in 2018 that the Trump team’s reason for seeking to end the DACA program was “virtually unexplained” in its legal arguments. 

Ahead of Trump’s inauguration, legal advocates indicated that Trump’s staffers have likely learned lessons and will sharpen their executive orders and directives with fewer mistakes this time around.

“We knew that they had better lawyers. We knew that they learned some lessons. I think now they’re smarter about it, they’re going to be more careful,” Rosenblum said. Still, there will inevitably be some mistakes, she continued, pointing to Trump’s first round of executive orders. Some “look like they’ve just been thrown together on a napkin,” Rosenblum said, while others “they’ve been working on for a long time.”

The landscape of federal courts is also different today from 2017. Trump’s judicial appointments not only led to the most conservative Supreme Court in decades, but he also shifted key appellate courts like the 9th Circuit to the right. Rosenblum is concerned about what this means for the future of cases that center on issues affecting historically marginalized groups like women, people of color and transgender people.

Well before Trump even won the 2024 presidential election, Democratic attorney general offices were planning. They did not know exactly what the wording of potential executive orders and other directives from Trump would say, but the attorneys did what they could to be more nimble on key areas like immigration. Their offices drafted memos, sample legal complaints and legal documents that could be used as templates when the time came to file a lawsuit, Rosenblum said.

After Trump won the election and reality set in, Democratic state attorneys general met in Philadelphia a few weeks later. There was extreme disappointment and reflection over the results, Rosenblum said, but the group was also determined to take on the work ahead. Some of Trump’s toughest legal critics issued statements about the results of the election, expressing their intention to fight for the rights of people in their states.

Massachusetts Attorney General Andrea Campbell wrote at the time that she is “clear-eyed that President-elect Trump has told us exactly what he intends to do as president, and that we need to believe him and to be ready for the challenges ahead.” 

New York Attorney General Letitia James echoed those sentiments in November. “My office has been preparing for a potential second Trump Administration, and I am ready to do everything in my power to ensure our state and nation do not go backwards,” she wrote. “During his first term, we stood up for the rule of law and defended against abuses of power and federal efforts to harm New Yorkers.” Since James took office in 2019, she and Trump have publicly clashed, particularly after her office sued Trump and the Trump Organization for financial fraud. Last year Trump said James has a “big, nasty, and ugly mouth” and called her “low IQ.”

To legal advocates, both state attorneys general and beyond, Rosenblum advised that it will be important to stay resilient, to partner up where appropriate, and to not let internal conflict get in the way of the larger mission of the work.

“I would not be surprised to see more actions being brought by attorneys general within the next few days, certainly weeks. And again, it’s a work in progress. It’s very fluid,” she said. “But the bottom line is, I know that the Democratic attorneys general are ready.