At the start of President Trump’s first administration, Skye Perryman joined a small legal organization, without even a website, bent on holding power to account.
Now, she runs the group — Democracy Forward — which is 53 lawyers strong and among the most formidable legal foes to Trump’s second term agenda.
Since Trump returned to the White House, Democracy Forward has filed nearly 100 legal actions against his administration, by its count, notching victories in more than a dozen cases spanning data protections from the Department of Government Efficiency (DOGE) to the release of billions of dollars in frozen funds.
In an interview with The Hill, Perryman said fighting Trump’s agenda has changed since 2017, forcing a recalibration of the legal defense against it. But Perryman believes it’s a fight worth working to win.
“I had the big task of taking what was a small startup organization with a promising proof of concept that very few people knew about and growing that into an institution that could really withstand and be a leader in the threats to our democracy,” said Perryman, Democracy Forward’s president and CEO.
“We’ve been building this organization to be able to address those challenges,” she added.
Perryman’s career started in Big Law, working for the firms Covington & Burling and WilmerHale for a decade before joining Democracy Forward’s founding litigation team in 2017, during Trump’s first term.
She left Democracy Forward after a year for another job but returned to lead the group in 2021 after the Jan. 6 Capitol attack.
Both Covington & Burling and WilmerHale are law firms that have found themselves in Trump’s crosshairs during his second term when he went after firms that employed attorneys tied to investigations against him or to his Democratic political rivals. Perryman was already with Democracy Forward when Trump took executive actions against them earlier this year.
Democracy Forward is now the most prolific private organization to take on the Trump administration in court — and all of its clients are represented pro bono, Perryman said.
The group represents plaintiffs in challenges to Trump’s federal funding freeze, immigration crackdown and DOGE’s access to federal agencies. It’s also involved in litigation against Trump’s firings of some independent agency members, the reductions in force across the federal government and efforts to dismantle several agencies, in addition to the administration’s clampdown on diversity, equity and inclusion (DEI) and other matters.
Democracy Forward has seen several prominent victories in court since Trump’s second term began.
Just a week into his presidency, Democracy Forward filed suit after the Office of Management and Budget (OMB) issued a memo directing federal agencies to temporarily pause “all activities related to obligation or disbursement of all Federal financial assistance,” creating chaos and confusion as many federal programs were paralyzed.
A federal judge temporarily blocked the memo on Jan. 28, and the next day, OMB rescinded the memo.
More recently, the group announced Tuesday that it obtained a five-page agreement between the U.S. and El Salvador in a lawsuit, revealing that the administration had barred any U.S. funds from being used to provide legal counsel to hundreds of Venezuelans sent to the Central American country’s notorious CECOT megaprison.
Democracy Forward’s focus has long been at the district court level, investigating and building out cases, because traditionally, that’s where there has been a gap in the “pro-democracy legal landscape,” Perryman said.
Once cases reached the appellate level, from appeals courts to the Supreme Court, they’d often attract pro bono representation from bigger law firms seeking to help shape the law or boost the appellate experience on their teams.
That’s changed since Trump took back the White House, with his targeting of law firms themselves. Though four firms have fought back in court, and all won at the trial level, other firms struck deals with Trump to avoid punishments.
“A new gap has emerged now that the nation’s most elite law firms — many of them — are not taking on the level of pro bono work that they used to take on, and that’s in that appellate space,” Perryman said.
“There are simply not that many appellate practitioners who are at law firms that are willing to cross the administration in this time,” she added.
Last month, the group launched its own appellate practice of about a dozen lawyers, citing the pullback from private law firms, in an attempt to start rebuilding that infrastructure.
Trump’s second presidency has shifted the playing field in other ways, from his attacks on lawyers and judges to a Justice Department less independent from the White House and more willing to dodge court orders.
To meet the moment, Democracy Forward has had to change the way it staffs cases to ensure there are enough resources and lawyers to “aggressively litigate compliance” with court orders, in addition to the underlying challenge, Perryman said.
Perryman said it’s a testament to the legal community’s greater preparedness for Trump’s second term than his first. A Democracy Forward-funded legal response center was launched on Inauguration Day to bolster Trump’s expected tranche of executive orders.
She added that, what hasn’t changed since Trump’s first term, is his administration’s “reckless disregard” for the processes and laws the government typically must abide by to implement its agenda, paving the way for challengers to prevail.
Hundreds of federal lawsuits have been filed challenging major administration actions, and they continue to mount.
Trump has attacked his legal opponents for filing “frivolous, unreasonable, and vexatious” lawsuits, directing Attorney General Pam Bondi in March to seek sanctions against attorneys and firms that engage in such action.
Perryman called that “bluster,” suggesting Trump’s challengers have a record in the courts so far that shows “the emperor doesn’t have any clothes.”
“We believe that one of the major levers of power that people have in this time is the ability to initiate litigation against their government, including against the president and his administration,” she said.
