President Donald Trump said on Friday he wanted an election-related lawsuit to be filed in Alaska. The man to do it for him was Stanley Woodward, the associate attorney general.

Holding the third highest ranking job at the Justice Department and having never appeared in federal court in Alaska before, Woodward has taken on that case’s unusual task — a fight to potentially block election certification if the incumbent Republican candidate loses — with little apparent help from other parts of his agency. (One assistant US attorney submitted and signed the filing under Woodward.) In other administrations — and even in prior months — election litigation hasn’t come from the associate attorney general’s office.

Yet the Alaska lawsuit capped a week where Woodward, a longtime DC attorney, had hustled to the forefront of the president’s personal agenda.

Earlier in the week, he spent a full day in court arguing what government witnesses could share in testimony about Trump’s plans for a golf course in Washington, DC. His argument and filings have lately echoed Trump’s frustration with some federal judges.

In recent weeks, Woodward at times has positioned himself as the Justice Department political appointee who could shield career Justice Department attorneys caught between the administration’s controversial positions and frustrated federal judges.

“It’s difficult to put my colleague in a position of contradicting the president,” he told a judge in Washington, DC, at the golf course hearing Monday, where he played clean up after a lower-level DOJ attorney struggled to square the government’s arguments with what Trump had said publicly about the case.

He was ordered to attend the hearing by Judge Ana Reyes after he was the sole signer of a court submission that responded to her yelling at a previous hearing because of the Justice Department’s handling of the case.

A longtime defense lawyer with ample trial-court experience after the January 6, 2021, Capitol riot and during the federal investigations into Donald Trump, Woodward landed in the Justice Department about a year ago, after serving as a White House attorney for Trump. Prior to Trump’s reelection, he had already been in the inner circle of lawyers around the president, personally representing Trump associates in the January 6 and classified documents criminal conspiracy investigations between 2021 and 2024. His clients have included now-FBI Director Kash Patel, and White House advisers Dan Scavino and Peter Navarro.

His work at the time gained notoriety and respect among several judges in the DC District Court for how frequently he was appearing before them.

Yet the persona has shifted this year, as Woodward has increasingly signed more extreme court filings, including ones that have mimicked Trump’s personal tone, in a case challenging the construction of the East Wing ballroom.

Woodward signed a court filing in April that said what the legal challengers were doing was “very bad for our country,” and that the plaintiffs, the National Trust for Historic Preservation, had “a beautiful name, but even their name is FAKE.”“This is a terrible, tremendously harmful case to the United States of America, and all it stands for!”Woodward also wrote to the court in the ballroom litigation.

More recently, Woodward has been especially critical of judges who have been making moves to rein in Trump administration priorities.

Woodward last weekend submitted a filing to Reyes asking for her recusal in the golf course case — a challenge to Trump’s plans to turn the course, which is accessible to the public at a modest price, to a more exclusive, championship-level venue. Woodward argued that the judge’s heated reaction to a sudden move by the administrations to cut down hundreds of trees showed a bias against the administration, and that her demeanor on the bench exhibited “histrionics.”

And on Tuesday, in unrelated cases in Minnesota, Woodward took aim at two different senior judges who are overseeing federal court cases for immigrants. The requests that senior judges Patrick Schlitz and John Tunheim recuse because of recent comments they made in the press that were critical of the administration’s immigration enforcement mirrored how Woodward approached Reyes by submitting the court filings separately from other Justice Department attorneys involved in the cases.

“The American people must be able to trust the impartiality of our Nation’s judges. Unfortunately, some judges have breached that trust … This [Justice Department] will not let that stand,” Woodward posted on the social media site X on Wednesday.

The prominent role Woodward has taken defending Trump’s wishes in court has, at times, made him the administration’s chief legal punching bag — including among critics of Justice Department leadership on the right.

Last week, the prominent far-right influencer and Trump ally Laura Loomer repeatedly attacked Woodward for his shepherding of cases over veterans’ claims and settlements following decades of water contamination in the 20th century at the US Marine Corps base Camp Lejeune.

Loomer has frequently pointed out that Woodward has past ties to Democrats as a lawyer in Washington. Attorney General Todd Blanche has publicly defended him several times.

Blanche worked alongside Woodward on legal defenses around Trump in 2023 and 2024, where the now-attorney general represented Trump personally and Woodward represented a co-defendant —Trump’s aide Walt Nauta — in the classified documents case.

“You are dead wrong about Stanley,” Blanche wrote to Loomer Tuesday on his official X account. “He is a patriot who is fighting for POTUS and the American people every day … Find a different obsession other than going after one of DOJ’s best fighters.”A Justice Department spokesperson said the department and Woodward’s work on Camp Lejeune settlements and efforts to protect veterans are “in lock step” with the Pentagon and the White House.

Woodward didn’t comment for this story Amid the attorney general’s defending Woodward from attacks from the conservatives, Woodward has continued to attempt to maintain his place in the DC legal community, which largely leans liberal.

This spring, he attended the retreat for the lawyers and judges of the DC federal courts, called the Circuit Conference, in Williamsburg, Virginia. His attendance surprised many of the lawyers there.

People who attended social events with Woodward in the evenings told CNN they witnessed him trying to chat with former Biden administration Associate Attorney General Vanita Gupta. But he also took flack in person from Matt Olsen, a former top national security attorney in Democratic administrations, who indicated to Woodward he thought he was a disgrace to his job. Both Olsen and Gupta declined to comment.

A Justice Department spokesperson responded to questions about those interactions by saying “being called a disgrace by a top deep state lawyer,” meaning Olsen, “should be viewed as a badge of honor” and that Woodward “of course can have respectful conversation with the former associate attorney general,” meaning Gupta.

The traditional role of the associate attorney general has been to oversee civil litigation handled by Justice Department headquarters in Washington, as well as cases related to the environment and natural resources, government approval of corporate mergers and tax-related matters.

“The associate position is one where the individual can have a pretty large say in how they execute the authority. There’s obviously a lot of civil litigation attorneys under the associate’s supervisory chain,” said Ed O’Callaghan, who served as a top Justice Department official during the first Trump administration.

“What I see him doing is saying, I am the top political appointee below the attorney general itself to argue the policies of the administration.”O’Callaghan noted that some associate attorneys general in the past have argued in court at their choosing, as Woodward is doing now, including Kevin O’Connor in the George W. Bush administration, who regularly appeared in federal appellate court arguments. “It’s not easy to do,” O’Callaghan added.

During Woodward’s daylong appearance in Reyes’ courtroom Monday, he was surrounded by no less than eight other Justice Department lawyers and officials in court.

He jumped in several times when Reyes was grilling a greener, career-level Justice Department attorney about the administration’s handling of the case.

“Someone is going to have to take responsibility for what is said in court,” Reyes said later in the all-day hearing on Monday after a Justice Department lawyer was unable or unwilling to answer Reyes’ questions.

Woodward jumped up and walked toward the front of the courtroom, ignoring the requirement to speak into a microphone.

“That’s why I’m here! He knows the law. Yell at me, not him,” he told Reyes.

The associate attorney general also took the lead objecting to questions posed to officials from the administration as they were asked to testify about conversations they may have had with government lawyers, or with the president himself.

At one point in the hearing, Woodward had objected so many times — citing executive privilege, confidentiality around government deliberations, or attorney-client communications — that he barely stood up from his chair to interject, staring at the counsel’s table in front of him as he listened.

“I’m sorry, your Honor,” Woodward said, apologizing for interrupting, hunched over and still looking down.

“Ok, you’re getting good at this,” Reyes said, referring to his success in shielding witnesses from answering, and without looking at him, she sustained his objection. The judge moved on to the next question.

At another point in the hearing, Woodward scrambled to object to questions lawyer Abbe Lowell was asking Department of Interior official Gregory Wischer, who visited the East Potomac golf course property with Trump and others in June.

Woodward noted he knew the case law around executive privilege because of his work on White House adviser Peter Navarro’s criminal contempt of Congress case in 2023, as he and Reyes discussed whether he would get a letter from the White House formally asserting privilege in the golf course litigation. “I don’t speak to the president directly,” Woodward told the judge.

A Justice Department spokesperson later clarified that Woodward does meet and speak to Trump, just not regarding official executive privilege assertions.