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.An unlikely rise in Trump’s orbitWoodward 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.A narrow escapeLaura 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.His portfolio includes oversight of the Justice Department’s civil-rights cases. Last year, he overruled other department officials who wanted a steeper sentence for a former Louisville police officer involved in the botched raid that resulted in the death of Breonna Taylor, according to people familiar with the matter.Woodward directed the lawyers instead to recommend one day in prison, arguing that because the shots fired by the officer weren’t the ones that struck Taylor, a lengthy sentence was unwarranted.

A judge rejected the bid and sentenced the former officer to 33 months.In Chicago last month, he took charge of a dismissed criminal case against U.S. Immigration and Customs Enforcement protesters that spurred allegations of misconduct against the prosecutors who filed it.

He rejected the court’s authority to appoint a special prosecutor to look into the prosecutors’ conduct.Courts have questioned why Woodward is inserting himself into cases and taking combative positions. Some of his most controversial legal submissions were signed by few, if any, other department lawyers, especially ones who are career attorneys.Bill Baer, a senior Justice Department official during the Obama administration, says it shows career lawyers “don’t see this as a merit-based decision making process whenever Stanley Woodward is this involved.”In an interview, Woodward said he intervenes in tough cases to show career attorneys “that I’ve got their backs.”Upending antitrust enforcementWoodward also has steered a Justice Department retreat in how it polices companies for anticompetitive behavior.Woodward, who oversees the antitrust division, has told DOJ lawyers he wants to avoid taking cases to trial and has driven settlements of high-profile lawsuits, including one that sought to break up the entertainment giant Live Nation.Early during his tenure, he threatened to fire several staff attorneys who opposed dismissing a lawsuit that challenged a merger in the travel industry, according to people familiar with the matter.

He later dropped the demand.Antitrust lawyers say the basis for Woodward’s recently ordered probe of television networks is thin, because their decision to pause pool coverage—a protest of the president’s removal CNN from a planned assignment—had no effect on consumer prices or other forms of competition.Woodward said he doesn’t expect every lawyer to agree with his view of the matter.“But what if I’m right?” he said. “Let a judge decide that.”Write to Dave Michaels at dave.michaels@wsj.com, Sadie Gurman at sadie.gurman@wsj.com and C. Ryan Barber at ryan.barber@wsj.com