The Justice Department is asking a federal judge to force the top two lawyers from Donald Trump’s White House counsel’s office to testify about their conversations with the former President, as it tries to break through the privilege firewall Trump has used to avoid scrutiny of his actions on January 6, 2021, according to three people familiar with the investigation. The move to compel additional testimony from former White House counsel Pat Cipollone and deputy White House counsel Patrick Philbin just last week is part of a set of secret court proceedings. Trump has been fighting to keep former advisers from testifying before a criminal grand jury about certain conversations, citing executive and attorney-client privileges to keep information confidential or slow down criminal investigators. But the Justice Department successfully secured answers from top vice presidential advisers Greg Jacob and Marc Short over the past three weeks in significant court victories that could make it more likely the criminal investigation reaches further into Trump’s inner circle. Jacob’s testimony on October 6, which has not been previously reported, is the first identifiable time when the confidentiality Trump had tried to maintain around the West Wing after the 2020 election has been pierced in the criminal probe following a court battle. A week after Jacob spoke to the grand jury again, Short had his own grand jury appearance date, CNN reported. All four men previously declined to answer some questions about advice and interactions with Trump when they testified in recent months in the secret criminal probe. Trump lost the court battles related to Jacob and Short before the chief judge of the trial-level US District Court in Washington, DC, last month. Attorneys for the men whom the DOJ is seeking to compel have declined to comment for this story or haven’t responded to requests. Cipollone and Philbin didn’t respond to requests for comment. A spokesman for the Justice Department also declined to comment. All four men have been willing to be as cooperative as the law demands, leaving Trump’s team to handle the fight over certain details in the investigation, the sources say. The litigation around Cipollone and Philbin’s testimony may be important for investigators in the long run, given how close the pair was to the Trump leading up to and during the Capitol riot. Prosecutors are likely to aim for the grand jury to hear about their direct conversations with the then-President. The disputes – conducted under seal in court because they involve grand jury activity – may also spawn several more court fights that will be crucial for prosecutors as they work to bring criminal charges related to Trump’s post-election efforts. Witnesses the federal grand jury has subpoenaed, such as former White House officials Mark Meadows, Eric Herschmann, Dan Scavino, Stephen Miller and campaign adviser Boris Epshteyn, also could decline to describe their conversations with Trump or advice being given to him after the election, several sources familiar with the investigation say. Trump and his allies have used claims of confidentiality – both executive privilege and attorney-client privilege - with mixed results in multiple legal quagmires that surround the former President. Those include the January 6 federal criminal investigation, the Mar-a-Lago documents federal criminal investigation, Georgia’s Fulton County investigation of election meddling, and the House select committee probe of January 6 as well. Some of the privilege arguments Trump has raised have never been settled in federal court, and some of the fights could lead to the Supreme Court. Trump spokesman Taylor Budowich slammed the “weaponized” Justice Department in a statement and referred to the probes surrounding the former President as “witch hunts.” Court fight so far According to the sources, the Justice Department won a trial-level judge’s order at the end of September that said Jacob and Short must testify in response to certain questions over which Trump’s team had tried to claim presidential and attorney-client confidentiality. The sealed court case, stemming from the grand jury’s work, had been before the chief judge of the DC District Court, Beryl Howell. Howell refused to put on hold Jacob and Short’s testimony while Trump’s team appealed, a source said. The Trump team, meanwhile, took several days to respond to their loss before Howell in court. The Justice Department set a quick-turnaround subpoena date for Jacob, leaving him to head into the grand jury under subpoena on October 6, according to several sources. The DC Circuit Court of Appeals is still considering legal arguments from Trump’s defense lawyers and the Justice Department over his ability to make executive and attorney-client privilege claims. How that is resolved – either by the appeals court or even the Supreme Court, if Trump pursues it that far – could have significant consequences for the January 6 criminal investigation, and for multiple witnesses who may be refusing to share some of what they know because of Trump’s privilege claims. Among a large group of former top Trump officials, Jacob has been one of the most searing voices condemning the then-President’s actions after the election, especially regarding the pressure he and his election attorney, John Eastman, tried to place on then-Vice President Mike Pence to block the congressional certification of the presidential vote. Jacob has been a harsh critic of Eastman, who is also of interest to prosecutors, dating back to when Eastman tried to convince Pence’s office the vice president alone could override the vote. He told Eastman at the time the right-wing attorney was a “serpent in the ear” of the President, and wrote while Trump supporters stormed the Capitol on January 6, 2021, “thanks to your bulls**t, we are now under siege.” Jacob added to a parade of star witnesses at public House select committee hearings this summer, speaking candidly about his disgust with what he witnessed inside the White House complex from his high-ranking position administration. “There is almost no idea more un-American than the notion that any one person would choose the American President, and then unbroken historical practice for 230 years, that the vice president did not have such an authority,” Jacob testified in July. But what Jacob and Short knew of Trump’s conversations, they wouldn’t disclose to the House nor to the grand jury until this month. In a taped House select committee deposition, Cipollone answered many questions about what happened inside the West Wing on January 6 but declined to describe communications between him and Trump. Cipollone’s and Philbin’s roles as White House lawyers raise complicated legal questions about whether Trump can claim confidentiality over the legal advice they gave him, as well as whether a former president can assert executive privilege to hold off criminal investigators. President Joe Biden has repeatedly declined to assert executive privilege around January 6 information, essentially leaving the fight for Trump to wage opposite the Justice Department. While the courts will look at each situation individually, history isn’t on Trump’s side. Federal prosecutors investigating former Presidents Bill Clinton and Richard Nixon were able to overcome attorney-client privilege assertions for White House counsel as well as executive privilege assertions so the grand jury could hear closely guarded information.