2008–2019 Woodward served as a
law clerk for three judges from 2008 to 2010: Judge
Vanessa Ruiz of the
D.C. Court of Appeals, and Judge Joan Zeldon and Chief Judge
Rufus G. King III of the
D.C. Superior Court. Woodward then worked for the law firm
Akin Gump Strauss Hauer & Feld LLP for 10 years, from 2010 until mid-2020. In 2018, Woodward was one of two recipients of the
D.C. Bar's Laura N. Rinaldi Pro Bono Lawyer of the Year award for
representing tenants facing eviction in the District.
2020–2025 He co-founded a law firm, Brand Woodward, Attorneys at Law, in 2020. as well as government and internal investigations and civil litigation. He has taught pre-trial litigation and employment law courses there. However, another finalist, Rupa Ranga Puttagunta, was appointed to fill the judicial seat. In September 2023,
House Judiciary Committee Chairman
Jim Jordan opened an investigation into allegations that
Jay Bratt, a senior prosecutor on
Jack Smith's team, improperly pressured Woodward by suggesting that his client
Walt Nauta's cooperation could benefit Woodward's candidacy for a federal judgeship. Bratt denied any impropriety occurred during his interactions with prosecutors. In 2023, Judge
Aileen Cannon agreed to a US Justice Department request to hold a hearing to examine potential conflicts of interest of Woodward, who represents both Trump's co-defendant Walt Nauta as well as potential witnesses in the
federal Mar-a-Lago classified documents case, and Trump’s offer to pay for the attorneys of those involved in his litigation. At the hearing, Nauta waived his right to a conflict-free attorney, and Cannon allowed Woodward to continue representing him. Notable clients of Woodward include: •
Oath Keeper Kelly Meggs — he was convicted of
seditious conspiracy for his role in the
January 6 attack on the
U.S. Capitol (Meggs was sentenced to 12 years in prison). • Ex-Trump aide
Kash Patel, whom Woodward represented in connection with Patel's
grand jury appearance related to Trump's retention of
classified documents and
national defense-related documents after his presidency. •
Federico "Freddie" Klein, a Trump administration staffer in the
State Department — he was convicted in July 2023 of violent participation in the January 6 attack (Klein was sentenced to 5 years and 10 months in prison). • Then-
House Minority Leader Kevin McCarthy and
House Minority Whip Steve Scalise — Woodward and his partner filed a brief on behalf of the Republican leaders in support of
Steve Bannon in the
criminal contempt of Congress case against Bannon (Bannon was found guilty, and sentenced to four months in prison). •
Peter Navarro, a former Trump aide — he was found guilty of criminal
contempt of Congress for defying a subpoena issued by the January 6 committee (Navarro was sentenced to 4 months in jail). •
Walt Nauta, Trump aide — he was
indicted alongside Trump on federal criminal charges in 2023 following an
investigation into Trump's retention and handling of classified documents and national defense-related documents after his presidency. Trump's
Save America PAC pays Woodward's legal fees for his representation of Nauta. •
Yuscil Taveras, Trump's director of information technology at Mar-a-Lago (named as "Trump Employee 4" in the indictment in the
prosecution of Trump on mishandling of documents). While represented by Woodward, Taveras testified to a
federal grand jury that he was unable to recall any discussions about security-camera footage at Mar-a-Lago. Taveras subsequently dropped Woodward as his attorney and cooperated with prosecutors in the investigation (including giving a
proffer session); Taveras acknowledged that his previous testimony had been false, and gave new testimony implicating Trump and Nauta.
Senior counselor to the U.S. president On January 5, 2025, President-elect
Donald Trump announced Woodward would serve as an assistant to the president and
senior counselor in his second term.
Associate attorney general In April 2025, President Trump nominated Woodward to serve as
United States Associate Attorney General. The
U.S. Senate confirmed him as part of a larger bloc of nominees on October 7, 2025. == Personal life ==