The Progressive Legal Group That Keeps Taking On Trump In The Courts – And Winning

WASHINGTON ― More than 5,000 people got their jobs back at the U.S. Department of Agriculture this month after a government employee oversight board concluded they had been illegally fired by Elon Musk’s Department of Government Efficiency.

The decision by that panel, the Merit Systems Protection Board, came after it restored the jobs of six other federal employees who had been similarly fired by DOGE.

Meanwhile, this month, a federal judge blocked DOGE from firing the president of a small federal agency, the U.S. African Development Foundation, in a lawsuit that provides the clearest details yet on how DOGE operates and how it may be routinely breaking the law.

All of these legal challenges came from the same group, a well-funded progressive legal organization, Democracy Forward.

At a time when the flood of litigation against President Donald Trump’s early actions is nearly impossible to keep up with ― his administration has already been hit with more than 130 legal challenges in the span of two months ― Democracy Forward has emerged as a leading legal organization that’s been slowing, if not stopping, some of Trump’s recklessness through the courts.

The group doesn’t just stand out for the number of lawsuits it’s been filing, which include more than 28 legal actions and 67 investigations since Trump was sworn in. Democracy Forward has shown it can move quickly to step in amid Trump’s chaotic, and often illegal, efforts to dismantle entire agencies, freeze federal spending, and fire thousands of federal employees. It has intervened on behalf of individual people, unions, nonprofit groups, health care professionals, educators, veterans groups and religious groups.

And importantly, it’s been winning.

On Saturday, Democracy Forward and the American Civil Liberties Union challenged Trump’s expansion of war time powers to deport immigrants using the centuries-old Alien Enemies Act. Within hours, a federal judge issued a temporary restraining order preventing Trump from removing some people through this act ― and later that day, broadened the scope of his order to cover all immigrants in danger of removal under the act.

In another case brought by Democracy Forward, a federal judge last week reaffirmed the court’s nationwide preliminary injunction (i.e., a temporary court order to preserve the status quo) that halted Trump’s efforts to arbitrarily terminate federal grants relating to diversity, equity and inclusion, and accessibility programs. The judge reaffirmed that not only can Trump not do that, but that this temporary halt applies to all agencies in the executive branch.

The group also secured the first and only nationwide order preventing Trump from imposing a sweeping freeze on trillions of dollars in federal spending, blocked a Trump administration policy enabling immigration enforcement officers to indiscriminately raid houses of worship, and this week prompted a federal judge to slam the Trump administration’s defense of DOGE and grant a request by labor and economic organizations to get more details about the Elon Musk-led entity unlawfully accessing sensitive data at federal agencies.

The evidence the Trump administration put forward to avoid more transparency into DOGE’s operations “is not the panacea they hoped it would be,” this judge concluded.

A big reason this organization has been so adept at countering Trump in court is because it spent the last 18 months gaming out legal strategies for responding to countless policy plans laid out in Project 2025, the far-right policy blueprint that the Heritage Foundation put together in preparation for a second Trump presidency.

Democracy Forward staff indexed the entire 900-page policy playbook, broke it down into different categories, put it in a spreadsheet and meticulously laid out what legal actions they should prepare to take based on how the Trump administration was likely to proceed with various policies, whether it be through executive orders, statutes or regulations.

They also coordinated with more than 450 civil society groups and state attorneys general to prepare for different scenarios where certain groups would be impacted by Project 2025 policies, and figured out when they should team up to defend the rule of law.

Trump tried to distance himself from Project 2025 on the campaign trail because lots of its plans are extreme and unpopular. But the policy guidebook was put together by former Trump administration officials and staunch allies, so it’s not surprising to see the president now moving aggressively to enact some of its proposals, like purging tens of thousands of federal workers for political reasons or abolishing the Department of Education.

In fact, late Thursday, Trump signed an executive order to dismantle the education department. Minutes later, Democracy Forward announced it would see him in court.

“Trump’s playbook is a known playbook,” Skye Perryman, Democracy Forward’s president and CEO, told HuffPost in an interview. “The Heritage Foundation wrote it down: Project 2025. We never believed it was a talking point or hyperbole. It is the greatest threat to democracy since the Civil War.”

Democracy Forward also prepared for a second Trump presidency by gathering materials from his first administration to review what legal actions and litigation he previously pursued, whether they be related to his executive orders, immigration cases, impoundment or challenges to executive orders issued by former President Joe Biden.

The president has done some unexpected things in his second term, like tapping Musk to oversee DOGE and letting him gain access to millions of Americans’ personal data. But Perryman said her organization was primed to respond to something chaotic, and in the case of DOGE, they sued on day one.

“This is like basic stuff,” she said.

“They do not play within the rules. There is opportunity in their lawlessness,” Perryman said. “They make a lot of legal foibles.”

Democracy Forward currently represents the American Federation of Teachers in two lawsuits, one that aims to halt DOGE’s seizure of millions of people’s sensitive data from the Social Security Administration, and another challenging a new Department of Education policy threatening to withhold federal money from schools teaching accurate history about slavery and diversity.

AFT, which has more than 1.8 million members, had been preparing to fight Trump’s executive order to dissolve the Department of Education when the department unexpectedly announced a new policy of stripping federal funds from schools that support diversity, equity and inclusion initiatives, said Daniel McNeil, general counsel at AFT. So the teachers’ group asked Democracy Forward if they wanted to team up to fight that, too.

“They already had something ready to go,” McNeil said. “It took working through the entire weekend to get it done, but they weren’t fazed at all by the fact that something else happened.”

AFT is working with other legal groups suing the Trump administration, he said, and they’re also doing good work. What’s unique about Democracy Forward’s model, though, is that they have their own attorneys doing the litigating versus hiring outside firms, and they have experts on staff, like someone who previously worked in the general counsel’s office at the Department of Education. They’ve also just been anticipating specific legal fights, he said.

“Of all the groups that were warning about Project 2025, they were systematically planning for the legal fight in the event that Trump were elected,” said McNeil. “For months in advance, they were thinking in a way that was like, ‘How do we challenge an executive order that does X? Who is the right party to challenge if Y happens?’ I think that’s what makes them different.”

Democracy Forward first launched in 2017, in response to what it described as the first Trump administration’s “unprecedented” threats to democracy and the rule of law. By 2019, it had sued his administration more than 100 times and chalked up several wins, including forcing the administration to collect pay data from employers based on race, gender and ethnicity, and forcing the FDA to regulate e-cigarettes.

Both Democracy Forward and its nonprofit counterpart, Democracy Forward Foundation, are chaired by Marc Elias, who served as general counsel for Hillary Clinton’s 2016 presidential campaign. The nonprofit is funded entirely by individual donors and philanthropic institutions. Its major donors include the Sandler Foundation, which gave $16 million from 2018 to 2023, and the Susan Thompson Buffett Foundation, which gave $5.6 million from 2021 to 2023.

Democracy Forward was operating with a budget of about $12.4 million in 2023, the most recent year its tax filings are available.

The organization has been hiring up for Trump’s second term. Last month, it brought on more litigators, public affairs specialists and operations personnel ― several of whom are seasoned former federal staffers from agencies that Democracy Forward will likely be seeing in court amid its lawsuits against the Trump administration, including the Justice Department, the Department of Health and Human Services, and the Interior Department.

One of its newest hires, Joel McElvain, was the acting deputy general counsel at HHS, where he was responsible for legal advice on all matters relating to Medicare and Medicaid statutes and the Affordable Care Act. Another recent hire, Michael Waldman, was special counsel at the Department of Veterans Affairs, where he advised the secretary on oversight matters and managed the department’s responses to congressional inquiries.

Shawn Phetteplace of Main Street Alliance, a network of roughly 30,000 small business owners that support left-of-center policies, has worked with Democracy Forward for years and is currently represented by them in three cases against the Trump administration. One case relates to the Office of Management and Budget’s freeze on billions of dollars on Jan. 27 in congressional approved federal grants being disbursed.

This funding freeze resulted in multiple small business owners having their money cut off, to the point where they weren’t sure if they could continue to operate, said Phetteplace. Within hours of OMB announcing its new directive, Democracy Forward requested a temporary restraining order in federal court. A judge granted that order on Feb. 3, and by Feb. 25, the judge granted a preliminary injunction, blocking the nationwide freeze from taking effect, for now.

“They keep winning,” Phetteplace said of Democracy Forward. “For our members, this isn’t theoretical. This is whether or not they stay in business.”

He chalks up some of the group’s success to the public-facing push it makes on the cases it’s fighting. He gave the example of Main Street Alliance members reaching out to the group to talk about how their businesses were hurt by Trump’s policies, and then how litigation has helped them. Democracy Forward has been incorporating those stories into its public statements as it moves forward with various lawsuits.

“They understand that it is really important to shape the public narrative around the issue and educate the public about the stakes,” he said. “That helps them make a stronger case.”

To be sure, Democracy Forward has faced setbacks in stemming Trump’s chaos, and that’s due to at least some of its victories being temporary. Last month, it filed emergency litigation in response to Trump’s plans to unilaterally defund the Consumer Financial Protection Bureau, a financial watchdog agency. Their quick legal action resulted in the administration backing off its plans, instead agreeing to wait until a related case was heard in court.

A federal judge has since heard that case ― and this week denied the plaintiffs’ request to halt the administration’s plans for CFPB.

Temporary wins are still wins. When a judge issues a temporary restraining order or a preliminary injunction, it immediately blocks an action and buys time. Preliminary injunctions in particular can drag on for a long time. Democracy Forward and other groups have already demonstrated that collectively taking these legal steps has a real effect on slowing Trump’s unlawful, everywhere-all-at-once approach to dismantling the federal government.

Democracy Forward chalked up another temporary, but significant, victory in one of its cases late on Thursday: A federal judge blocked DOGE workers from accessing Social Security systems, calling the Musk-led efforts at this agency a “fishing expedition.”

“This is a major win for working people and retirees across the country,” said Lee Saunders, president of the American Federation of State, County, and Municipal Employees, one of the plaintiffs in the case. “This decision will not only force them to delete any data they have currently saved, but it will also block them from further sharing, accessing or disclosing our Social Security information.”

Some Trump allies are mad at the success that Democracy Forward and other groups have found in the courts, particularly in cases where judges have issued nationwide injunctions halting some of the president’s actions. In a nonsensical show of fealty to Trump, Sen. Josh Hawley (R-Mo.) on Thursday vowed to introduce legislation to prevent U.S. district court judges from issuing nationwide injunctions ― something that is, in fact, their jobs.

“That is not a power that I think district courts have,” Hawley, a Yale Law School alum who knows better, claimed on The Charlie Kirk Show, a far-right podcast. “Either the Supreme Court needs to intervene and make clear there’s only one court that can issue rules for the whole country … and/or, if they won’t do that, Congress needs to legislate and make clear that district courts do not have the ability to issue these kinds of injunctions.”

For her part, Perryman said one reason it’s important to slow things down in the courts is because it creates transparency on what Trump is actually doing. Doing so gives Americans a better understanding of the illegality of his actions, she said, and forces his administration to keep answering for what it’s doing.

“Understand that chaos is part of the strategy,” she said.

“Every day in litigation, what we see in this administration is they back off,” Perryman added. “Because really, the purpose is to see what they can do quickly. They don’t hold great conviction. There is opportunity in that.”