At the beginning of President Trump’s first term, Sky Perryman became part of a small legal organization that had a website focused on managing important legal issues.
Now, she leads Democracy Forward, a robust group comprising 53 lawyers, which has become a formidable legal challenge to Trump’s agenda for his second term.
Since Trump’s return to the presidency, Democracy Forward has filed almost 100 legal actions against his administration, securing victories in over a dozen cases, including those related to government data protections and the release of funds that had been frozen.
Perryman shared in an interview that Trump’s approach to his agenda has shifted since 2017, necessitating a re-evaluation of his legal strategies. Still, she believes the fight is worth the effort.
“I started by documenting small, nascent organizations that, while not widely known, have the potential to become key players in defending our democracy. It’s alarming how few people realize their growth,” said Perryman, who serves as the president and CEO of Democracy Forward.
“We’ve been diligently building our organization to tackle these challenges,” she added.
Perryman’s career took root at a major law firm before spending a decade at Covington & Burling and Wilmer Hale. She joined the litigation team at Democracy Forward during Trump’s first term in 2017.
After briefly stepping away for another role, she returned to lead the group in 2021 following the January 6 Capitol attack.
Both Covington & Burling and Wilmer Hale found themselves in Trump’s sights during his second term because they employed lawyers who were connected to either him or his political rivals. Perryman had already been active with Democracy Forward when Trump initiated actions against them earlier this year.
Democracy Forward is now recognized as the most active private organization challenging the Trump administration in court, providing pro bono representation to all its clients, according to Perryman.
The organization advocates for plaintiffs against Trump’s federal funding freezes, immigration policies, and access issues concerning federal agencies. Moreover, it is involved in lawsuits that address the administration’s restrictions on diversity, equity, and inclusion (DEI), among other matters.
Since Trump began his second term, Democracy Forward has celebrated several noteworthy court victories.
A week after he took office, the group filed a lawsuit following a memo from the Office of Management and Budget (OMB) that froze all federal financial assistance obligations, leading to widespread confusion and halting numerous federal programs.
A federal judge temporarily blocked the memo on January 28, only for OMB to retract it the next day.
Recently, the organization highlighted a legal contract that revealed the administration was blocking U.S. funds intended to offer legal assistance to hundreds of Venezuelans detained in a notorious Central American prison.
Democracy Forward’s emphasis has long been on investigating and building cases at the district court level, addressing what Perryman describes as a gap in the “legal environment of democracy.”
When cases escalate to the Court of Appeals or the Supreme Court, they often attract major law firms looking to shape legal precedents.
This dynamic changed significantly with Trump’s second presidential term, propelling major law firms into the spotlight. Four firms actively pushed back against Trump’s actions in court, achieving numerous wins, while others negotiated settlements to evade repercussions.
“Currently, many of the country’s top law firms are not engaging in the pro bono activities they once pursued. It highlights a new vacuum,” she noted.
“It’s tough to find appeal practitioners at firms who are willing to engage at this level, especially given the current administration,” she added.
Last month, Democracy Forward initiated its own appeals division with about 12 lawyers, responding to the reduction in support from private law firms and aiming to rebuild that infrastructure.
Trump’s second term has shifted the landscape within the Justice Department, which now appears closely intertwined with the White House’s agenda, complicating matters for legal practitioners and advocates.
To adapt to this reality, Democracy Forward had to change how it approached cases to ensure there were adequate resources and lawyers available to actively litigate.
Perryman believes that the legal community is now better prepared for the challenges of Trump’s second term than it was during his first. The organization established a Legal Response Center on inauguration day to brace for Trump’s anticipated executive actions.
However, one constant remains: the administration’s apparent “reckless neglect” of legal processes and regulations.
Hundreds of federal lawsuits have emerged, challenging significant administrative actions, and more continue to be filed.
Trump has countered by filing what many describe as “frivolous” lawsuits against his legal challengers. Recently, Attorney General Pam Bondi called for sanctions against lawyers and firms involved in these actions.
Perryman interprets this as mere “bluster,” suggesting that Trump’s challengers have consistently demonstrated in court that he is lacking substance. “One of the most powerful tools people have right now is the ability to sue the government, including the president and his administration,” she stated.
