Meet the legal nerd who MAGA bigwigs are turning to for help

Stanley Woodward wasn’t supposed to be here, at the epicenter of the most contentious legal matters facing Trump world.

But now he’s everywhere.

On Oct. 19, the veteran attorney was in court representing Oath Keeper Kelly Meggs, one of several people charged with seditious conspiracy for actions at the Capitol on Jan. 6, 2021. That night, just before midnight, he filed a brief on behalf of Dan Scavino, the longtime aide to Donald Trump fighting a subpoena from the Jan. 6 select committee. The next day, Woodward escorted ex-Trump aide Kash Patel to a grand jury appearance related to Trump’s retention of sensitive records at his Mar-a-Lago estate.

Woodward’s eye-opening client list goes on. He represents Trump aide Walt Nauta, another figure of interest to prosecutors investigating the Mar-a-Lago documents, and Ryan Samsel, a prominent Jan. 6 rioter accused of igniting the Jan. 6 breach. He and his law partner — Tip O’Neill-era House counsel Stan Brand — filed a brief on behalf of GOP Leader Kevin McCarthy during the contempt of Congress proceedings against Steve Bannon. And he’s currently representing Peter Navarro, whose criminal trial for defying a Jan. 6 committee subpoena is slated to begin in early 2023.

“I’ll sleep when I’m dead,” Woodward said wryly when a reporter commented on his crushing workload as he entered the courthouse on that Oct. 19 morning.

A few days later, Woodward almost fulfilled his prophecy, when a car collided with the scooter he was driving, sending him to George Washington University hospital. While there, he underwent shoulder surgery. While in recovery, he was wheeled to the delivery room to witness the birth of his fourth child, who is now a month old.

Among a crew known for their big personalities and in-your-face political postures, the mild-mannered Woodward may be the most prolific Trump-world warrior you’ve never heard of. That’s exactly how he prefers it.

Tall, bespectacled and bearded, Woodward stands out in a courtroom packed with clean-cut attorneys and paralegals. In the courtroom, he speaks with the certitude of a lawyer who has done his homework. During breaks, he flits around with the harried demeanor of a man with a daunting roster of high-maintenance clients.

Those who know Woodward say Trumpian figures are drawn to him precisely because he’s what many lawyers who end up in Trump circles are not. He’s neither a bomb-thrower nor a headline-seeker. He’s a law nerd in a world of political operatives. And it’s the separation he has from the Trump loyalty-at-any-cost mentality that’s made him in demand among MAGA figures embroiled in the legal morass that followed Trump since Jan. 6.

“The usual suspects of Trump world are tired and discredited,” one Woodward associate said. “People are lucky to have him. He’s not operating with blinders on.”

Between October 2021 and Sept. 30, 2022, Trump’s Save America PAC shelled out $120,000 to Brand Woodward Law. Prosecutors have raised questions about public news reports suggesting that several Oath Keepers, including Kelly and Connie Meggs, have had legal expenses paid by a group led by Sidney Powell, a former Trump attorney. Woodward and his co-counsel Juli Haller — a Powell ally — declined to publicly indicate whether they had accepted funds from Powell’s group but said they were in compliance with all rules pertaining to potential attorney-client conflicts.

Woodward’s actual politics are a bit of a black box. But what is known suggests someone not exactly of the MAGA mold. He works with Brand, himself a product of the Democratic-run House of the 1980s, and has eschewed overt political commentary. Woodward’s wife, Kristin McGough, is an accomplished criminal defense attorney and counsel to the Washington Lawyers' Committee for Civil Rights and Urban Affairs, which is focused on reducing racial disparities in the criminal justice system.

Woodward’s still-young career has been bookended by national and international crises. After graduating from Catholic University’s Columbus School of Law in 2008 and clerking for three judges in the Washington, D.C., court system, he joined the big law firm Akin Gump in the throes of the mortgage crisis that tanked the U.S. economy. Brand said the conflicts and strictures of big law firms grated on both of them.

Woodward primarily worked on complex civil litigation — from matters stemming from the financial crisis to the Foreign Corrupt Practices Act. He would remain at Akin Gump until mid-2020 when, as Covid lockdowns gripped the world, he decided to take a chance on Brand, who had been cajoling him to start their own practice focused on congressional and white-collar investigations.

“The world has changed, seemingly overnight,” Woodward wrote in a social media post announcing his decision to leave Akin Gump. “What I know is that at home, with my three young boys, I am resolved to join the fray. … Am I afraid? Yes. But with Stan, I hope to make a difference.”

Prior to his foray into Trump world and Jan. 6 defendants, Brand was known as one of the most aggressive defenders of congressional prerogatives on behalf of Tip O’Neill’s House of Representatives. His expertise in congressional investigations made him in high demand after he left Congress. Scavino became a client of Brand’s prior to his departure from Akin Gump and remained with him after he joined forces with Woodward.

Today, Brand prefers to operate as the architect of legal strategies while his mentees execute those strategies in court. His tutelage has boosted the careers of several prominent attorneys who became high-profile figures during the Trump years. They include Abbe Lowell, who represented Jared Kushner during the Mueller investigation, and Stephen Ryan, who represented ex-Trump lawyer Michael Cohen. He says Woodward may be his best find of the bunch.

“This guy has extraordinary capacity to juggle balls and to understand in depth the legal concepts and issues, and pick them up very quickly,” said Brand.

But there are limits to the skills Woodward possesses and deploys in service of some of the most polarizing figures to face criminal and legal consequences following the Jan. 6 attack on the Capitol. Good lawyering can only get a client so far.

Meggs, on Tuesday, became one of the first Americans convicted of seditious conspiracy in more than a decade. And after the verdict came in, a dejected Woodward declined to speak to reporters. “The fight goes on,” he said, an indication of a likely appeal for Meggs, who faces decades in jail.

Woodward also represents Samsel, who charged at police barricades on the early afternoon of Jan. 6, a moment many believe was the trigger point of the entire Capitol breach. He also represents Freddie Klein, a Trump-appointed State Department official who spent hours amid the mob at the most notorious hot spot of Jan. 6 violence, the Lower West Terrace tunnel.

Navarro, meanwhile, stands accused of defying a congressional subpoena from the Jan. 6 committee, which sought to interview him about his effort to derail the transfer of power by working with GOP lawmakers to challenge Joe Biden’s electors. And Scavino, who avoided a contempt of Congress charge despite declining to appear before the Jan. 6 committee, was a prominent surrogate for Trump’s false claims about the 2020 election results and was present for many conversations with Trump in the weeks before Jan. 6.

But whether Woodward feels a moral conflict about the clients he has chosen and the cases he’s arguing is beside the point, Brand said in an interview.

“The fact that it’s Trump is happenstantial. No one I’m aware of has asked us what our political bona fides are,” said Brand. “What they care about is, how do we practice defense? There’s no litmus test for us.”

Brand noted that throughout history, attorneys associated with one party or another have taken high-profile clients who might cut against their politics. Edward Bennett Williams, the treasurer of the DNC in the 1970s, represented mobsters. William Hundley, an ally of Robert Kennedy, went on to represent Watergate clients.

“That’s the slice of life in Washington that has always existed,” Brand noted.

Ryan described Woodward’s success as a relatively simple formula: Strong and persuasive writing, a genuinely likable persona and a willingness to take on polarizing clients, particularly after the Jan. 6 attack on the Capitol.

“After 1/6, there was a lot of, I think, reluctance in the white-collar bar to take some of these people,” Ryan said. “I know of lawyers who normally are fearless about taking someone who’s unpopular. I think there was a stigma after 1/6 on some of these people.”

While Trump and his allies are often known to attack the very justice system that will determine their fate, Woodward forged amicable relationships with judges and the prosecutors he litigates against, as has been on display at various moments during the Oath Keepers trial.

A few days after his late-October scooter accident, Woodward returned to the courthouse, right arm in a sling, to resume Meggs’ seditious conspiracy defense. His return was greeted by DOJ and defense attorneys, as well as U.S. District Court Judge Amit Mehta, with a warm round of applause. On Nov. 14, when Mehta and another Oath Keeper defense attorney debated whether to introduce evidence about his client’s use of the potent pain medication Opana, someone jokingly chimed in, “Mr. Woodward can testify.”

“I would characterize him as an amazingly intelligent man with a deep grasp of the rules of evidence,” said Lee Bright, a Texas-based defense lawyer for Oath Keepers founder Stewart Rhodes. “That, compounded by a commanding presence in the courtroom, results in his being a formidable attorney to have as your advocate.”

Woodward knows he’s playing a tricky hand in some of these cases. Jan. 6 defendants have been almost universally convicted by Washington, D.C., juries, and while jurors are vetted and selected for their pledges to be impartial, defense attorneys have repeatedly raised worries that D.C.’s antipathy for Trump could create an even greater obstacle to an acquittal. Woodward sought to blunt those issues as he appealed to jurors for an acquittal.

“I won’t ask you to agree with Mr. Meggs’ political beliefs, his preference for the president of the United States,” Woodward told the Oath Keepers jury during Nov. 3 arguments. “I will ask you to read, to hear the evidence in this case, the messages, and to decide whether the evidence was a plan, a scheme — something nefarious — or whether, as others have observed, they represent hyperbole, political rhetoric.”

Ultimately, the jury disagreed.

It’s not just his quantity of high-profile clients that has drawn murmurs among fellow lawyers and the reporters who cover the many matters Woodward is involved in. He’s also been tasked with litigating some of the most complex challenges facing Trump world, including Trump’s ability — or lack thereof — to assert executive privilege as an ex-president.

Woodward spent a recent Friday sparring with Mehta over whether a private conversation between Trump and Navarro — with no witnesses but the two men — can be enough to prove Trump attempted to assert the privilege.

Woodward noted that Navarro would be unlikely to testify about the conversation, since doing so would waive his Fifth Amendment rights against self-incrimination. Mehta noted that there was one other person Woodward could call to vouch for Navarro’s version of the conversation.

“I don’t want to do that,” Woodward replied, describing Trump as a witness “who I don’t want to be involved in the process.”

Woodward’s allies say it’s not lost on him that his work on these matters, though, could reverberate across history — that a man in a sling who spends his limited spare time constructing Lego sets with his kids could shape the contours of presidential power.

It’s a remarkable place for Woodward to be. And one others didn’t imagine for him. Ryan noted that Woodward has been in contention for a D.C. Superior Court judgeship, selected in November 2020 by the district’s Judicial Nominating Commission as a finalist for a presidential nomination to fill a vacancy. But given the trajectory of his career and his decision to take on a raft of polarizing clients, he said it’s unclear whether that path will materialize again.

“These things do mark you,” Ryan said. “Life is never the same after you do these kinds of things.”