Top Lawyer Faces Rare Losses Defending Trump’s US Attorney Picks

A longtime Justice Department attorney and former solicitor general of Florida faces an uphill battle defending how the Trump administration elevated loyalists to top US attorney posts.

Henry Whitaker, who has more than a decade of DOJ experience, suffered a loss this week when a three-judge panel for the US Court of Appeals for the Third Circuit ruled Alina Habba, a former personal attorney for President Donald Trump, is unlawfully serving as the top federal prosecutor in New Jersey.

Whitaker, now counselor to the attorney general, represented Habba in October oral arguments in the case and has also led DOJ’s defense of Lindsey Halligan, an insurance lawyer with no prior prosecutorial experience, as interim US attorney for the Eastern District of Virginia. A federal judge has since disqualified Halligan—a ruling the White House said it plans to appeal.

In both cases, Whitaker’s arguments have failed to sway federal judges, showcasing the difficulty even the most seasoned lawyers face in arguing the Trump’s administration legally installed loyalists with unorthodox backgrounds to US attorney posts, legal scholars say.

“It is a challenge to be Trump’s lawyer because there is no law usually supporting his actions and Trump cares most about the political theater,” said Michael Gerhardt, a University of North Carolina law school professor and former special counsel to the Senate Judiciary Committee.

“That is a high mountain to climb,” Gerhardt said.

Whitaker, a former deputy at DOJ’s Office of Legal Counsel, returned to the department this year with two US Supreme Court wins as Florida’s top appellate lawyer. He’s held in high esteem among former colleagues who say his background makes him more than capable of serving as the face of the administration’s defense in these cases.

DOJ spokesperson Natalie Baldassarre referred to Whitaker in a statement as a “brilliant legal scholar and litigator whose expertise on the Appointments Clause is unmatched.”

Whitaker hasn’t appeared in other challenges to US attorney appointments, including a hearing Thursday challenging the top prosecutor in the Northern District of New York.

Uniquely Qualified

While at DOJ’s legal counsel office during the first Trump administration, Whitaker was deeply involved in advising the executive branch on key legal issues, including political appointments, said Dechert LLP partner Steven Engel, who led the office.

This experience gave Whitaker “a strong understanding of many of the relevant appointment statutes,” including the Federal Vacancies Reform Act and the attorney general’s statutory authority to temporarily appoint an interim US attorney for a 120-day period, Engel said.

Before moving to OLC, Whitaker spent almost nine years in DOJ’s Civil Division.

During Joe Biden’s administration, he became Florida’s solicitor general, where he maintained his reputation as a “top-notch legal advocate,” said Jason Hilborn, a partner at Boies Schiller Flexner LLP who worked in the state office under Whitaker’s leadership.

Whitaker, a 2003 Harvard Law School graduate and former clerk for Justice Clarence Thomas, successfully defended Florida before the Supreme Court two times—the first in 2022 upholding the state’s authority to collect Medicaid reimbursements, and the second two years later defending a law regulating large internet platforms.

Bryan Gowdy, a shareholder at Creed & Gowdy, P.A. who argued opposite Whitaker in the Medicaid case, said he’s “not surprised that” Whitaker “would get tapped for this type of high-stakes litigation.”

“We both had respectable arguments,” Gowdy said of the case, in which justices sided with Florida’s right to seek reimbursements from court settlements allocated for future medical care.

Whitaker also secured a notable win in the Florida Supreme Court last year when justices ruled the state constitution’s right to privacy doesn’t protect abortion access.

Defending Trump

Whitaker is facing a novel challenge defending Habba and Halligan’s appointments, attorneys and law professors say.

The cases “raise interesting, unsettled issues,” said Miguel Estrada, a partner at Gibson, Dunn & Crutcher LLP, where Whitaker worked in the early 2000s.

Whitaker has sparred with federal judges over the unusual steps DOJ took to elevate Habba and Halligan to their roles, as well as securing controversial indictments against former FBI Director James Comey and New York Attorney General Letitia James (D).

At the Third Circuit appeals court in October, Senior Judge D. Brooks Smith questioned Whitaker on the series of steps DOJ took to install Habba. This included the firing of a court-appointed first assistant, Trump’s withdrawal of Habba’s nomination to the Senate, and Habba’s resignation as interim US attorney before her appointment as “special attorney” and acting US attorney.

“Can you come up with an example of any kind” of such a sequence of events regarding “the appointment of the United State attorney?” Smith asked.

“Well, I guess, I cannot,” Whitaker said at the time, but argued Habba’s designation was “consistent with longstanding practice” of DOJ, and that the executive branch has in “analogous contexts” exercised its authority through delegation.

Whitaker again defended DOJ’s approach on Halligan, another former personal lawyer for Trump, in federal court in Alexandria, Va., in November. He described an improper citation in Attorney General Pam Bondi’s order appointing Halligan as interim US attorney as a “paperwork error,” and maintained that the plain text of the appointments statute allows the attorney general to make multiple interim appointments.

In each case, Whitaker’s argument “simply ignores or evades” the 120-day law, said Robert Weisberg, a law professor at Stanford University.

Courts have so far agreed, with US District Judge Cameron McGowan Currie ruling last month that the government’s reading of the appointments statute would allow for interim US attorneys to serve indefinitely without Senate confirmation.

With the potential for appeals in both cases, Whitaker faces the challenge of encouraging the Fourth Circuit appeals court and the Supreme Court to overturn lower court rulings that have so far rejected the Trump administration’s contested US attorneys appointments.

“Statutes actually give any president some flexibility to temporarily fill vacant posts, but the courts here are agreeing that the Trump administration is overstepping that flexibility,” University of Michigan law professor Nina Mendelson said.