Court Action Underscores Peril for Trump in Documents Investigation

The behind-the-scenes legal fight over obtaining evidence from a lawyer who represented former President Donald J. Trump in the investigation into his handling of classified documents has brought into sharper view where the Justice Department might be headed with the case.

According to the wisps of information that have seeped out of sealed court filings and closed-door hearings, prosecutors believe they have compelling evidence that Mr. Trump obstructed the government’s efforts to reclaim the sensitive records and may have even misled his own lawyers.

This theory of the case has not changed much since federal agents obtained a search warrant in August based on three possible crimes, obstruction being one of them. The search turned up hundreds of sensitive government records being kept at Mar-a-Lago, Mr. Trump’s heavily trafficked compound in Florida, after his lawyers had earlier assured the Justice Department that all such documents had been returned.

Still, the more recent developments stemming from efforts to force testimony and other evidence from the lawyer, M. Evan Corcoran, in Federal District Court in Washington, indicate that prosecutors have continued to build a case and that the inquiry remains a serious threat to Mr. Trump.

On Wednesday, a federal appeals court weighed in on the matter, ruling that Mr. Corcoran had to give the government what is likely to be dozens of documents related to his work for Mr. Trump as well as return to a grand jury on Friday to answer questions he had previously sought to avoid with assertions of attorney-client privilege.

The appellate ruling effectively let stand the decision of a lower-court judge, Beryl A. Howell, who gave a blunt assessment of the case last week. In a sealed order issued on Friday upholding the crime-fraud exception to attorney-client privilege, Judge Howell noted that prosecutors in the office of the special counsel, Jack Smith, had made “a prima facie showing that the former president committed criminal violations,” according to people familiar with the decision.

The crime-fraud exception allows prosecutors to pierce attorney-client privilege when they have reason to believe that a client — in this case the former president — used legal advice or legal services in furthering a crime.

Most notably, in a lengthy memorandum of law that accompanied the ruling, Judge Howell, according to two people briefed on the matter, laid out damning assertions made by prosecutors that Mr. Trump knowingly deceived the government and caused Mr. Corcoran to misstate to prosecutors where the documents were being held at Mar-a-Lago.

The existence of Judge Howell’s order and memorandum was first reported by ABC News. Shortly after the ABC report appeared, Mr. Trump’s campaign attacked it as “Fake News” and “ILLEGALLY LEAKED.”

“There is no factual or legal basis or substance to any case against President Trump,” Steven Cheung, a spokesman for Mr. Trump, said of Judge Howell’s ruling. “The deranged Democrats and their comrades in the mainstream media are corrupting the legal process and weaponizing the justice system in order to manipulate public opinion because they are clearly losing the political battle.”

Mr. Smith’s office is likely still far from making any charging decisions. And the arguments that prosecutors presented to Judge Howell about possible crimes committed by Mr. Trump have not faced the scrutiny they would in a venue like a trial, where the burden of proof is much higher.

Still, the accumulation of details emerging from the proceedings suggests that Mr. Smith and his team are drilling down on every scrap of evidence they can find in assembling an argument that Mr. Trump may have impeded a federal investigation. For their part, some of Mr. Trump’s aides have stated plainly if privately that the government — and, in their minds, Judge Howell — see him as “a criminal.”

All this has taken place in spite of predictions from Mr. Trump’s allies that the documents investigation would quietly blow away after President Biden was also found to have kept classified materials after his term as vice president. A special counsel, Robert K. Hur, is investigating Mr. Biden’s handling of the documents.

Mr. Corcoran, who testified before the grand jury earlier this year, is set to appear before the grand jury again on Friday in compliance with rulings from both Judge Howell and the appeals court. According to two people familiar with the events, he is not intending to invoke his Fifth Amendment right against self-incrimination when he testifies, underscoring that he is not the target of the special counsel’s scrutiny.

In their initial motion to compel Mr. Corcoran’s testimony, prosecutors also sought to invoke the crime-fraud exception to get testimony from a second lawyer, Jennifer Little, who is based in Atlanta. Ms. Little represents Mr. Trump in the Fulton County, Ga., district attorney’s investigation into his efforts to overturn his loss in that state in the 2020 election.

Prosecutors are interested in Ms. Little because she was one of the few criminal defense lawyers working directly with Mr. Trump when the Mar-a-Lago matter heated up at the Justice Department, according to two people briefed on the matter. She counseled Mr. Trump to be cooperative, the people said, and left the case soon after Mr. Corcoran was brought on by Mr. Trump.

Judge Howell ordered Ms. Little to testify before the grand jury in her recent ruling, the people briefed on the matter said. They added that Judge Howell said Ms. Little did not have to turn over a document she had sought to withhold from prosecutors.

Ms. Little and her lawyer did not respond to messages seeking comment.

The extraordinary back-and-forth in the past several weeks between Mr. Trump’s lawyers, Mr. Corcoran and his lawyers, and Mr. Smith’s prosecutors — not to mention with multiple witnesses who are also Mr. Trump’s lawyers, as well as all of their lawyers — has turned the federal courthouse in Washington into a bustling hive of Trump-related inquiries.

The latest example came on Thursday when lawyers for Mr. Trump — including Mr. Corcoran — appeared before a new chief judge, James E. Boasberg, with lawyers for former Vice President Mike Pence. They were there to discuss some issues related to Mr. Pence’s testimony before a grand jury investigating Mr. Trump’s efforts to overturn the 2020 election, an inquiry also being overseen by Mr. Smith, the special counsel.

Late last month, prosecutors under Mr. Smith filed court papers seeking to stop Mr. Pence and Mr. Trump from asserting claims of executive privilege to limit the scope of Mr. Pence’s testimony. Representatives for Mr. Pence have said the former vice president would also seek to pare back his testimony by invoking the “speech or debate” clause of the Constitution, which is intended to protect the separation of powers.

Judge Boasberg, after hearing arguments on both subjects, said he would issue a decision later, according to a person familiar with the matter.