Former U.S. President Donald Trump gives the keynote address at the Faith & Freedom Coalition during their annual “Road To Majority Policy Conference” at the Gaylord Opryland Resort & Convention Center June 17, 2022 in Nashville, Tennessee.
Drew Angerer/Getty Images

Some executive privilege battles litigated in civil cases have dragged out for years. One, involving a House subpoena for Justice Department documents related to the Operation Fast and Furious gunrunning investigation, stretched for seven years, from 2012 to 2019.

However, the courts tend to fast-track grand jury subpoena battles because of the priority given to criminal investigations.

“The Department of Justice can get in front of a court really fast, unlike Congress,” said Eggleston, the former Obama White House counsel. “They can do that in a matter of days. They can work so much faster and they don’t really have to negotiate.”

Legal experts say the reported grand jury subpoenas to Cipollone and Philbinraise issues beyond the traditional executive privilege ones because they were, at times, giving Trump legal advice that would normally be protected by attorney-client privilege. However, in a 1998 dispute stemming from Independent Counsel Ken Starr’s probe of President Bill Clinton’s White House, the D.C. Circuit ruled that governmental attorney-client privilege had to yield to a grand jury subpoena in the context of a criminal investigation.

“The D.C. Circuit is very explicit that government attorneys do not have any greater privilege than other advisers when it comes to information they have that is relevant to a grand jury,” said Ryan Goodman, a New York University law professor and co-founder of the Just Security blog. “I think it’s highly likely that Trump will lose very quickly because … there’s case law in the D.C. Circuit contradicting any such claims.”

One former White House lawyer for Trump, Ty Cobb, said he thought some of the recent court rulings might have been mistaken to hold that a former president couldn’t assert executive privilege if the current one disagreed.

“I’m not sure that that is right,” said Cobb, who has publicly broken with Trump and called his actions related to Jan. 6 “disqualifying.”

However, Cobb acknowledged that either way, current law says criminal investigators can get even information protected by that privilege if they show “an urgent need” and “no other place to go” for it.

“If you tick those boxes, you can be questioned,” he said. The attorney noted, though, that some witnesses might choose to invoke their Fifth Amendment rights regardless of, or in addition to, any privilege Trump might assert, and the right against self-incrimination is largely treated as sacrosanct.

The initial stages of any executive privilege fight over grand jury testimony about Trump would go to Chief Judge Beryl Howell, an Obama appointee and former Senate Judiciary Committee counsel who has repeatedly voiced outrage about the Jan. 6 attack.

Beyond that, Trump’s lawyers can take the issue to the D.C. Circuit, which already snubbed him in the White House records fight, and on to the Supreme Court, which did the same.

The only outward sign of hesitation from the Justice Department on executive privilege issues is its decision last year not to bring criminal charges against Meadows and Trump’s social media guru, Dan Scavino, for defying House subpoenas based on what they said were instructions from Trump.

But the department’s recent backing for the House in Meadows’ civil suit seems to indicate that Justice Department officials are committed to their view that the stronger legal argument here is that, as a former president and because of the gravity of the Jan. 6 events, Trump cannot successfully assert the privilege to block testimony.

Indeed, some legal observers say Trump’s chances of succeeding in this sort of court battle are so remote that he might not even choose to fight it out. A privilege battle that attorney John Eastman pursued in court against a House subpoena led to a judge ruling in March that Trump likely committed a crime — obstruction of justice — by trying to interfere with the certification of electoral votes by Congress on Jan. 6, 2021.

One potential downside for Trump if he does put up a privilege fight over the grand jury demands is a repeat of what happened in the Eastman case, with a judge or multiple judges publicly declaring that he probably broke criminal law. It wouldn’t amount to a criminal charge, but would fuel public perceptions that Trump crossed the legal line in his activities trying to overturn President Joe Biden’s win at the ballot box.

“There’s a potential risk for Trump that a judge holds there’s sufficient evidence of his engaging in criminal conduct,” said Goodman, the New York University law professor, a possibility that might dissuade Trump from embarking on a quixotic legal battle to shield his advisers from testifying about their conversations with him.