As Donald Trump’s second-term agenda accelerates, Democracy Forward and its fast-growing coalition of litigators are mounting an aggressive legal blockade — battling executive overreach, Supreme Court fast-tracking, and internal tensions on the left while reshaping the future of resistance lawyering.
At a discreet office suite just blocks from the White House, Skye Perryman stared into a bank of monitors as a dozen senior litigators dialed in. They were there for what has become a near-daily ritual: a strategy session to dissect the next round of emergency legal battles against the Trump administration.
As president again, Donald Trump has unleashed a sweeping wave of executive actions—from civil service purges to agency reorganizations to immigration crackdowns—at a speed that outpaces even his tumultuous first term. And Democracy Forward, the once-niche progressive legal advocacy group Perryman leads, is now positioning itself as the central operational headquarters for the legal resistance.
Midway through the meeting, the team received news they had been dreading: The administration had petitioned the Supreme Court for an emergency stay—again—this time to reverse a lower-court decision blocking the firing of the U.S. Copyright Office director. It was a reminder of the group’s two greatest adversaries: the pace of Trump’s agenda and a Supreme Court increasingly willing to greenlight it.
Welcome to the new legal battleground of Trump 2.0.
A Quiet Office Becomes the Nerve Center of Anti-Trump Litigation
 |
| Democracy Forward President and CEO Skye Perryman, right, takes part in a meeting in her office in Washington, Oct. 27, 2025. |
 |
| Democracy Forward employees are seen in the legal organization’s offices in Washington, Oct. 27, 2025. |
Democracy Forward, founded in the aftermath of Trump’s 2016 victory, has spent years building its infrastructure. But under Perryman—a Covington & Burling and WilmerHale alum who took over after Jan. 6—it has transformed into a sprawling, 150-person machine, half of them lawyers, filing hundreds of lawsuits across nearly every policy domain.
The group no longer just occupies part of a floor. It is expanding across two full floors, adding a moot court, war rooms, and enhanced security. Its address is no longer public. Armed security and traveling protection details have become routine.
The scale matches the ambition: Democracy Forward reported $18 million in contributions in 2023, but Perryman says they are pushing to raise more than $100 million this year—money needed to keep pace with an administration that is testing every boundary of presidential authority.
The Coalition: 650 Groups Unified Under “Democracy 2025”
Perhaps Perryman’s biggest accomplishment is Democracy 2025, a massive umbrella coalition of more than 650 organizations, including:
- The Brennan Center for Justice
- National Immigration Law Center
- Public Citizen
- Dozens of state and local legal advocacy groups
“The goal,” Perryman says, “is to fill a gap in the anti-Trump litigation world—to be the connective tissue.”
Not All Allies Are Comfortable With the Group’s Size
But the meteoric rise has triggered unease. Some attorneys on the left worry that Democracy Forward’s scale may dominate donor dollars, overshadow smaller advocacy groups, and narrow the diversity of legal approaches.
Historical parallels loom large: The Center for Constitutional Rights was born from disagreements with the ACLU and later became essential in fighting Bush-era detention policies.
Perryman’s response is blunt:
“Fighting an autocratic threat is not a training exercise. You cannot fight autocracy by the spoonful.”
A New Model of Lawyering: Courtroom + Media War Room
Unlike more traditional legal groups, Democracy Forward devotes equal energy to public messaging.
Each morning, Perryman joins her public affairs chief, Melissa Schwartz—a former Biden official—to map the media strategy. Perryman appears regularly on cable networks, offering sharp, lawyerly critiques of Trump’s executive overreach.
“Some organizations want to put all resources into pure lawyering,” she says. “But we’re fighting on multiple fronts—the courts, the press, and the politics.”
This hybrid model is designed for a world in which the administration files late-night emergency petitions and the Supreme Court moves cases in hours.
The Supreme Court: The Biggest Obstacle Yet
 |
| The U.S. Supreme Court building is seen in Washington, Oct. 17, 2025. |
Democracy Forward has notched wins in lower courts—blocking civil service firings, halting access to Americans’ Social Security data, and slowing agency dismantlement. But these victories often evaporate once they reach the Supreme Court’s emergency docket.
In July, the Court’s conservative supermajority allowed the Trump administration to continue dismantling parts of the Department of Education, overturning Democracy Forward’s injunction.
These shadow-docket stays rarely address the merits, but they allow irreversible actions to proceed anyway.
Attorney General Pam Bondi recently said the quiet part out loud:
“We’re not winning in a lot of district courts… When we get to the Supreme Court, the right thing happens.”
For Perryman, the challenge is structural:
“We are litigating in an environment where the administration is using the emergency docket at high volumes—and where most of the justices seem open to it.”
History, Legitimacy, and the Stakes for American Democracy
 |
| Democracy Forward President and CEO Skye Perryman poses for a portrait in the legal organization’s offices in Washington, Oct. 27, 2025. |
With the Supreme Court facing its lowest public approval ratings in decades—and 43% of Americans believing the Court is “too conservative”—Perryman argues that the institution itself faces a crisis.
“This Court must decide: Will it preserve our democratic institutions, or will it help dismantle them?”
What is clear is that corporate leaders, major law firms, and powerful institutions cannot remain neutral.
As Perryman puts it:
“No one’s going to get out of this moment intact by keeping their head down.”
The legal resistance is no longer a shadow network—it is a fully mobilized, war-room-equipped counterforce confronting an administration that is redefining presidential power. And its success or failure will shape the American constitutional order for decades.
======
-- By Michele Robinson
Jessica Perry contributed to this report
© Copyright 2025 JWT Communications. All rights reserved. This article cannot be republished, rebroadcast, rewritten, or distributed in any form without written permission.
No comments:
Post a Comment