Associate Attorney General Stanley Woodward Jr., once a defense lawyer connected to President Donald Trump’s inner circle, has become the Justice Department’s go-to for the most politically sensitive court cases.
He’s a fixer, of sorts, but his appearance on the docket or a legal filing often signals a more contentious turn. The cases are high profile, close to Trump’s interests and frequently at moments when judges are thwarting the president’s will.
Katie Phang, a journalist who sued the government over the administration’s rollout of files related to notorious sex offender Jeffrey Epstein, said she came up with a nickname for the annoyance she experienced when he showed up in her case.
“I call Woodward ‘the seagull.’ You know when you’re at the beach and one swoops in and steals your french fries?” she said.
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Woodward, the DOJ’s No. 3 ranking official, a position which has historically been managerial only, appeared on a filing in her high-profile case after the government did not comply with a court-ordered deadline to produce documents, including records that mention allegations against Trump.
He also swooped in to preemptively challenge the results of the Senate race in Alaska, a move that was criticized as a Trump administration attempt at affecting the outcome of the election there. He has defended the president’s vision of a giant White House ballroom and tangled with the judge blocking work at the D.C. golf course Trump wants to overhaul.
The political appointee was the sole DOJ signer on the settlement agreement in Trump’s lawsuit against the IRS that set up a $1.8 billion fund “anti-weaponization fund” — an agreement a judge later concluded was the result of Trump and the Justice Department manipulating the judicial process for the “imprimatur of legality for an unlawful settlement.”
Last week, Woodward dropped into three separate cases to demand that judges be disqualified from matters connected to Trump priorities, part of the Trump administration’s pushback against judges they say have treated the government unfairly.
In Minnesota, Woodward signed a judicial misconduct complaint in September against two federal judges over comments they made to The New York Times related to the Trump administration’s immigration crackdown in the state.
Last week, he signed motions to kick those judges off of two immigration cases, accusing the judges of “improper political commentary” that he said raised doubts about their ability to fairly adjudicate the cases.
And in D.C., he has stepped into a challenge to Trump’s plans to renovate and expand a golf course at East Potomac Park. He’s seeking to disqualify Judge Ana Reyes, who has blocked work on the project and held a tense three-hour hearing in which she harshly criticized the government for having deceived her with its actions related to tree removal over a recent holiday weekend.
In a motion, Woodward called her behavior “nothing short of egregious” and “histrionics.”
It’s a case Trump has inserted himself into as well, with social media posts that describe the plans, criticize Reyes and declare that the course will be closed to start the project Nov. 15 regardless of the courts. “The judge has absolutely no right to hold up this very important and beautiful Project,” Trump posted.
Woodward had told Reyes at an Oct. 19 hearing that there was no plan to close the course on Nov. 15 — and then in a Wednesday filing, he said plans to close it that day are now underway.
Woodward is currently listed as a lawyer in at least 19 cases filed since Trump returned to power, according to court records, more involvement in ground-level litigation than typical for the nation’s associate attorney general, a role that has traditionally overseen all U.S. government civil litigation.
“It is, in my experience, unprecedented,” said Bill Baer, who had that job as acting associate AG for nearly a year during the Obama administration and had previously spent years reporting to that office.
Previous associate attorneys general have held weekly meetings with the divisions that handle civil rights, antitrust and environmental cases to develop strategies for defending the presidential administration’s most important issues.
During the previous administration, the job meant figuring out how to shape the defense of President Joe Biden’s student loan program and face off against corporate superpowers such as Apple and Ticketmaster. But under this administration, Woodward has added another task to his portfolio: appearing in court to personally press Trump’s will.
During a podcast in May with America First Legal, the conservative outfit started by White House deputy chief of staff Stephen Miller, Woodward said that “what gets me up in the morning is knowing President Trump understands very clearly why the Justice Department is and was in need of reform. He has tasked me with the awesome responsibility of helping us get there.”
And he noted the outsized importance of the DOJ — and his responsibilities overseeing its civil litigation — fighting over the legality of Trump’s executive orders in an attempt to secure court rulings that will hamstring the next president from simply revoking them with the stroke of a pen.
“The president keenly understands that his legacy will be shaped by the outcome of the litigation that is happening in the courts over the executive actions that he is taking,” Woodward said.
Baer called it “shocking” that an associate attorney general would insert themselves in ongoing litigation rather than direct it from afar with general strategic advice, saying that Woodward’s personal involvement hints at the administration’s difficulty in getting career prosecutors to put their names on filings.
“That’s a signal right there that career people who understand their ethical obligations to the public, their ethical obligations to the bar, are not willing to put all that at risk to support a brief that is lacking in legal merit,” he told The Washington Sun.
DOJ spokesperson Katie Kenlein, addressing questions about why an official of his rank has inserted himself into so many cases, said the department “can’t speak to why previous [associate attorneys general] were not involved.”
“Are you critiquing Stanley wanting to do his job/suggesting DOJ would be better off with someone who wasn’t so ‘involved?’ I’ll point you to his quote which still stands,” she wrote in an email.
Kenlein directed The Sun to a 2022 Politico story where Woodward was quoted as saying, “I’ll sleep when I’m dead.” That story also described Woodward as a legal nerd and “neither a bomb-thrower nor a headline-seeker.”
Woodward said in the May podcast he had “virtually no agenda” coming into the Justice Department, and pointed to his experience with the tactics of Biden-era prosecutors as something that led him to his current role.
“I frankly never saw myself working in the Department of Justice, because everything that the department stood for, especially in the last four years, was antithetical to what I believed,” he said.
Long before Woodward became a Trumpworld insider, he graduated from Catholic University of America’s law school and later returned to teach pretrial litigation and lead its alumni council. He became licensed to practice law in Washington in 2010 and eight years later earned recognition from the D.C. Bar — the same one he’d later attack — by becoming its pro bono attorney of the year for representing poor tenants who faced eviction. His growing local reputation got him recommended by the local Judicial Nominating Commission for a spot on the D.C. Superior Court bench in 2020.
His eventual dive into the legal circles of MAGA began in the months after the Jan. 6, 2021, attack on the Capitol building. Woodward represented several rioters, including the wife of an Oath Keeper and a former Trump State Department employee. In the summer of 2022, he started defending Peter Navarro, a former Trump White House official who had boasted about a failed plan to keep Trump in power dubbed “Green Bay Sweep” — and was convicted of contempt of Congress after refusing to testify about it before the House Jan. 6 Committee.
Earning the trust of the MAGA cause, he was tapped to represent Walt Nauta, Trump’s valet who was accused of helping Trump try to hide boxes of records when federal investigators were looking into classified documents located at his private Mar-a-Lago estate.
One moment in August 2022 came to define Woodward’s alignment with MAGA — and cemented his relationship with Trump, according to a source familiar with the situation. Woodward, as the attorney for Nauta, met with prosecutors who’d eventually become part of Special Counsel Jack Smith’s team.
In Woodword’s version of the story, the prosecutors expressed a desire to obtain Nauta’s cooperation against Trump, but one of them said he didn’t take Woodward to be a “Trump attorney” — and casually mentioned how Woodward was up for a judicial nomination.
Defense lawyers reported it to a D.C. federal judge as a veiled threat of political retribution. Trump’s defense lawyer circle used the incident in the Mar-a-Lago case as evidence of vindictive prosecution — and sources cited it to The Washington Sun in late 2024 as a key element in the incoming Trump administration’s quest for retribution.
“It showed his loyalty,” said a source familiar with the episode.
Woodward said on the podcast that Trump was prosecuted under a novel theory that had never been tested, and 300 Jan. 6 participants were prosecuted under a theory that the Supreme Court two years later concluded was wrong.
“I feel like we were aggressively prosecuting on novel theories, and that just makes my blood boil,” Woodward said. “But the president asked me to come, and as you all know, when the president asks, you don’t say no. Although I did twice, and the third time, it was clear what the ultimatum was, and so here we are.”
He spent the first months of the new administration as a White House lawyer before getting Trump’s nomination to be the No. 3 at the DOJ.
Woodward digitally signed a Justice Department motion back in April defending Trump’s planned White House ballroom that was widely noticed for a style more closely resembling a Trump Truth Social post than a legal filing.
“‘The National Trust for Historic Preservation’ is a beautiful name,” it said. “But even their name is FAKE because when they add the words ‘in the United States’ to the National Trust for Historic Preservation, it makes it sound like a Governmental Agency, which it is not.”
It mocked the trust, saying “they suffer from Trump Derangement Syndrome.” And the use of all caps continued later: “Congress has never dictated or tampered with the zoning, permitting, or architectural aspects of any Project, especially one being given FREE OF CHARGE AS A GIFT TO THE COUNTRY!”
Kenlein, the DOJ spokesperson, did not answer a question about whether Woodward had written the legal briefs on his own or was taking dictation from Trump. However, she defended his recent filings taking on district court judges.
“Judges are routinely persecuting lawyers who take positions contrary to their views. Woodward has consistently been willing to stand up on behalf of line prosecutors who represent the American people,” she said in an email.
Woodward has a tendency to show up when a case reaches an inflection point, according to several people involved in those cases, who say he appears either when the understaffed and overwhelmed DOJ mishandles a case or when a politically sensitive issue is at stake.
“He shows up like a bad penny,” Phang said.
In Phang’s Epstein-related case, Woodward formally appeared the day after U.S. District Judge Emmet Sullivan ordered the DOJ to comply with Congress’ new law and produce documents, such as FBI agents’ handwritten interview notes, foreign-language materials and records that mention allegations against Trump.
The DOJ hadn’t bothered to file an answer in court — blowing the initial deadline by 90 days and submitting one only after Phang’s lawyers asked the judge to compel the government to do so. When the government finally did, the document bore the names of Woodward and Andrew Block, a senior counsel at the associate attorney general’s office.
And it came with Trumpian flair, calling Trump “the leader of the most transparent Presidential Administration in the history of this great Nation,” and describing DOJ’s effort to release the Epstein files as a “Herculean task.”
Woodward swooped into a Massachusetts fight over offshore wind turbines in January, just four days before arguments over whether Vineyard Wind could challenge the Trump administration’s decision to block — on national security grounds — a $4.5 billion project that was 95% complete and had been producing power for over a year.
Trump has long been an enemy of tall turbines and renewable energy, and the halt came from his executive order targeting the industry. Woodward appeared for a scheduling conference ahead of the arguments, and his name was on a recent status update indicating that the national security “review remains ongoing.” That same month, he appeared in another lawsuit over a halted wind energy project in New York.
In September, Woodward entered the fray in an ongoing lawsuit over the Trump administration’s new dietary guidelines. Mark Kennedy, an attorney with the Physicians Committee for Responsible Medicine, said in an interview that the new guidelines are “central to this new MAHA concept” — and that a government loss in court would be a huge setback for the White House.
“This would throw all that away,” Kennedy said.
And Woodward signed the DOJ’s lawsuit in May attempting to block the D.C. Court of Appeals from disciplining Jeffrey Clark, a high-ranking DOJ official in the first Trump administration who played a role in the president’s attempts to overturn the 2020 election by drafting a proposal to have the DOJ issue a letter to swing states citing supposed irregularities to pressure them to appoint alternative electors.
The knives came out last week, when MAGA influencer Laura Loomer accused Woodward of mishandling a case involving government settlements for U.S. military service members who claim they were exposed to contaminated drinking water at Marine Corps Base Camp Lejeune. She called him a “Democrat Associate Attorney General who is low balling sick US Marines who have been diagnosed with cancer.”
Several Trump-aligned conservatives rose to Woodward’s defense. Blanche himself posted a reply, calling Woodward “one of DOJ’s best fighters” and a “patriot who is fighting for POTUS and the American people every day.”
The attorney general also noted who at DOJ makes the decisions about Camp Lejeune settlements, “consulting with and keeping the White House counsel’s office.” Later that night, Trump himself weighed in on the litigation strategy at a campaign rally in North Carolina — and tied it directly to politics.
“If we win the House and the Senate, I am directing the Department of Justice to settle all remaining legitimate claims as soon as possible, and get it off the books and get it finished,” the president said. “So if we don’t win, there’s no money. If we do win, you’re getting it.”
On Tuesday, DOJ said it “had approved 3,780 more settlements for $860 million more than the previous administration. We are in lock step with the White House and Department of War on protecting our veterans.”
One former top DOJ official, speaking to The Washington Sun, expressed incredulity that Woodward could have time for run-of-the-mill lawyering. The cracks might be starting to show.
In the Alaska lawsuit, a federal judge is fast-tracking the case and has already expressed skepticism over the timing of the suit, which came “after Alaskans had already begun casting their ballots.”
On Tuesday, a state lawyer representing Alaska in the case, racing to meet the court’s deadline, noted that the listed DOJ attorney in the case had referred her to Woodward.
“When I called Mr. Woodward, I got his voicemail and left a message,” attorney Margaret Paton Walsh wrote. “I have not heard back from him at the time of filing.”
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