How a Former Democrat Became Trump’s Bulldog at the Justice Department

WASHINGTON—When a signature cause for the Trump administration is on the ropes and judges are asking tough questions, Stanley Woodward puts himself in the fight. Woodward, 43 years old, says he is hard-charging because the Justice Department has a limited amount of time to carry out Trump’s plans.

“Another two years and 77 days,” he said in a recent interview.Woodward, the Justice Department’s third-ranking official, in recent weeks signed a lawsuit that sought to block certification of the Alaska Senate election results if the Republican candidate lost and ordered an antitrust investigation of television networks that had agreed to suspend their pooled coverage of President Trump.

He has also confronted judges in multiple recent cases, arguing they are biased against the president. Earlier this year, he was the official who signed the administration’s settlement with Trump that created a nearly $1.8 billion “anti-weaponization” fund that is now defunct.

Woodward’s willingness to put his name behind controversial legal actions had led some officials to joke behind his back that his initials really stand for Sign Whatever, according to people familiar with the matter. His approach has gone beyond endorsing the department’s positions.

In a low-key but unyielding manner, he has dueled with judges who expressed concern that Trump is exceeding his powers. “Yell at me, not him,” Woodward told a judge last month, referring to a colleague who faced a grilling over Trump’s plans to remake a historic public golf course.

Woodward, 43 years old, says he is hard-charging because the Justice Department has a limited amount of time to carry out Trump’s plans. “Another two years and 77 days,” he said in a recent interview. His role could grow further as Trump is signaling a combative second half of his term, including on Saturday when the president called on the Justice Department to investigate congressional Democrats who are planning oversight of his administration.

“All those critics who want to stand on the sidelines and tell me that I’m a dummy, what I say to them is, then get in the arena,” Woodward said. Woodward grew up near Philadelphia before attending American University and law school at Catholic University in Washington, D.C., and was a registered Democrat during the years after he graduated.

He spent a decade at law firm Akin Gump working on a variety of business and environmental cases, a tenure that lasted through much of Trump’s first administration. The D.C. Bar Association named him pro bono lawyer of the year in 2018, for efforts such as representing low-income housing tenants facing eviction.

He left Akin after his colleagues declined to make him a partner. In 2020, he and fellow Akin attorney Stan Brand started their own small firm. They represented Trump loyalists facing legal scrutiny, including Kash Patel, now the director of the Federal Bureau of Investigation.

Woodward cemented his MAGA credentials during special counsel Jack Smith’s case alleging that Trump illegally retained classified documents at his Mar-a-Lago home. The lawyer represented Trump’s personal aide, Walt Nauta, who was charged in the case.

He takes credit for arguing that Smith wasn’t lawfully appointed, a position accepted by U.S. District Judge Aileen Cannon, who dismissed the case. In his Justice Department office, Woodward keeps a large framed photograph showing him walking with Trump and Nauta outside the White House Rose Garden.

Laura Loomer, a Trump-aligned influencer who attacks government employees she deems unfit to execute the president’s agenda, has said Woodward should be fired. Trump almost did so in April. This spring, around the time Trump fired Pam Bondi as attorney general, he weighed replacing Woodward with Harmeet Dhillon, the head of the civil rights division who reported to Woodward and sought the promotion, people close to her said.

Woodward persuaded the White House to keep him in place, and his star has risen ever since. Dhillon announced last week that she was leaving. Woodward declined to comment on the episode. Woodward has steered resources toward Trump’s immigration priorities, including filing lawsuits against universities, states and cities over tuition benefits for undocumented immigrants and challenging local laws that ban federal agents from wearing masks that conceal their identities.