Pat Cipollone saw a lot as Trump's White House counsel. He could have a hard time shielding information from a federal grand jury.

• Pat Cipollone received a subpoena to testify before a grand jury in the January 6 investigation.
• Cipollone invoked executive privilege in previous testimony before the House January 6 panel.
• Prosecutors could have an easier time getting information from the Trump White House counsel.

Inside a nondescript conference room, former Trump White House counsel Pat Cipollone delivered unsparing assessments last month of the former president and his allies' desperate attempts to overturn the 2020 election.

But, seated beside his lawyer, Cipollone would only go so far in his closed-door testimony before the House committee investigating the January 6, 2021, attack on the Capitol. When asked about direct discussions with Trump, he invoked executive privilege to keep those communications confidential.

Now faced with a grand jury subpoena, Cipollone is expected to have a more difficult time shielding those discussions behind privilege.

The grand jury subpoena to Cipollone marked just the latest sign that the Justice Department is closing in on Trump and his inner circle as it investigates efforts to reverse the former president's loss to Joe Biden. With Cipollone, the grand jury has demanded testimony from Trump's top White House lawyer who was privy — and opposed — to machinations to prevent the peaceful handoff of power.

Cipollone appeared to invoke executive privilege without significant pushback from the House January 6 committee. But legal experts said federal prosecutors can more easily pierce that privilege in the pursuit of new details about Trump's conversations and conduct around January 6.

"Usually the privilege involves the legislative branch seeking information from the executive. Here, it's the executive branch, in the form of DOJ, seeking its own information," said Randall Eliason, a George Washington University law professor and former top public corruption prosecutor in the US attorney's office handling January 6 cases. "The current president has not asserted privilege. Plus, it's a limited privilege, and can't be invoked to hide information about a possible criminal offense."

Indeed, more than two decades ago, a federal appeals court in Washington, DC, noted that executive privilege "can be overcome upon a proper showing of need for the evidence in criminal trials and in grand jury proceedings."

In 1998, the US Court of Appeals for the DC Circuit addressed a White House lawyer's claims of executive privilege and so-called "government attorney-client" privilege as a basis for refusing grand jury inquiries about his conversations with then-President Bill Clinton. At the time, Clinton was facing an investigation into whether he committed perjury and obstruction of justice in connection with a sexual harassment lawsuit, in which he was a defendant.

In the case, involving deputy White House counsel Bruce Lindsey, the DC Circuit delivered a forceful call for government lawyers to reveal any evidence of criminal wrongdoing.

"When an executive branch attorney is called before a federal grand jury to give evidence about alleged crimes within the executive branch, reason and experience, duty, and tradition dictate that the attorney shall provide that evidence," the DC Circuit ruled. "With respect to investigations of federal criminal offenses, and especially offenses committed by those in government, government attorneys stand in a far different position from members of the private bar. Their duty is not to defend clients against criminal charges and it is not to protect wrongdoers from public exposure."

Neil Eggleston, who argued the Lindsey case on behalf of the Clinton White House, predicted last month that Cipollone would receive a grand jury subpoena. Writing on the blog Just Security, Eggleston outlined the "many good and overlapping reasons" why other top Trump administration lawyers — including former Attorney General William Barr and other Justice Department officials — concluded they could detail their dealings with the former president.

"In the grand jury context, it is only more apparent that any assertion of privilege would collapse: the relevant legal privileges belong to the very branch of the federal government that would be conducting the investigation, and a balancing analysis would overwhelmingly favor DOJ's need for testimony over any countervailing consideration," wrote Eggleston, who served as White House counsel at the end of the Obama administration.

"This conclusion is bolstered," he continued, by the DC Circuit's ruling in the Lindsey case.

That ruling is likely to come into play as the Justice Department reportedly prepares a court fight to force former White House officials to testify about Trump's conversations and conduct around January 6. According to CNN, which first reported the Justice Department's preparations, prosecutors are expecting Trump to raise executive privilege claims to shield information from the federal grand jury as it increasingly scrutinizes the former president's inner circle.

In recent appearances before the grand jury, two former Vice President Mike Pence's top aides — Marc Short and Greg Jacob — declined to answer questions about their direct interactions with Trump, CNN reported. Ahead of their testimony, their defense lawyers and prosecutors outlined questions they would avoid to skirt potential privilege issues, with the possibility of returning to those areas of inquiry at a later date.

At its latest public hearings, the House January 6 committee played footage of its recorded interview with Cipollone, who praised Pence for refusing to bow to pressure from Trump to unilaterally block the certification of Biden's victory. Cipollone suggested in his testimony that Pence should receive the Presidential Medal of Freedom and called January 6 a "terrible day for this country."

In his testimony, Cipollone also recounted how he batted away some of Trump's most bizarre ideas for holding onto power. For instance, he recalled his concerns about a plan to have the military seize voting machines, even after several top administration officials told Trump that his claims of widespread election fraud were baseless. And he remembered being "vehemently opposed" to Trump's consideration of Sidney Powell, a conservative lawyer known for her embrace of conspiracy theories, to lead a special counsel investigation into election fraud. 

"You don't get too much closer to Trump than the White House counsel," Eliason told Insider. "If you're talking about signs they're moving up the ladder, the Pence aides were one sign, and this is a more significant one. He has the potential to provide some really valuable information that would be very damaging to the president."