Two lawyers for Donald Trump could become witnesses or targets in the obstruction investigation connected to the criminal probe of the former president’s unauthorized retention of highly-sensitive government documents at his Mar-a-Lago resort in Florida, according to legal experts.

Photograph: Steve Helber/AP
Photograph: Steve Helber/AP© Provided by The Guardian

The lawyers – Christina Bobb and Evan Corcoran – face becoming ensnared in the investigation because they liaised with the justice department during the government’s months-long effort to retrieve boxes of presidential records and classified documents from Trump’s Florida home.

Related: Trump Mar-a-Lago home searched over ‘likely’ efforts to hide files, DoJ says

At issue is an interaction that took place on 3 June in which, according to a court filing submitted by the justice department in a separate but related case on Tuesday, the two lawyers made representations that they had complied with a grand jury subpoena that subsequently proved to be false.

That day, the justice department’s chief of counterintelligence, Jay Bratt, and three FBI agents travelled to Mar-a-Lago to collect the documents that had been subpoenaed, the filing said, and Bobb and Corcoran turned over a taped, Redweld envelope of classified materials.

But before Bratt departed, Bobb produced and signed a letter certifying that all and any documents responsive to the subpoena were being turned over, while Corcoran indicated that the records the government had sought were confined to one storage room, the filing said.

The trouble for the two Trump lawyers is that the justice department then developed evidence through multiple sources that additional presidential and classified documents remained at Mar-a-Lago – which proved to be the case when the FBI searched the property two months later.

According to the search warrant and court filings, the justice department is investigating among other crimes whether there was potential obstruction of justice with respect to how Trump and his lawyers have seemingly been resistant to return documents belonging to the government.

An itemized list of property seized in the execution of a search warrant by the FBI at Mar-a-Lago, signed upon receipt by Christina Bobb. Photograph: Jim Bourg/Reuters
An itemized list of property seized in the execution of a search warrant by the FBI at Mar-a-Lago, signed upon receipt by Christina Bobb. Photograph: Jim Bourg/Reuters© Provided by The Guardian

The justice department’s account of the 3 June episode – what it has described as a “likely” effort to conceal presidential and classified documents sought by the government – raises the prospect that both Bobb and Corcoran could become witnesses in the obstruction investigation.

But the case, and how the justice department might approach the issue, remains complex.

The question for federal prosecutors becomes whether the two Trump lawyers willfully misled the justice department so that Trump could keep the documents, or whether the lawyers made the representations because they themselves were misled by Trump.

To establish the exact circumstances surrounding Bobb’s confidence in signing the certification, and Corcoran’s confidence in his statements, legal experts said, the justice department would probably have to move to subpoena both of the lawyers for communications and testimony.

Such a step would immediately run into an issue about attorney-client privilege, since the kind of information the justice department would be trying to extract for a potential obstruction case targeting Trump would be protected communications between Trump and his lawyers.

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The privilege exists to protect the rights of defendants who might have committed an offense, since they need to be able to speak candidly with their lawyers about what happened without the fear that prosecutors could use their discussions against them at a trial.

The protection can be removed through the so-called crime-fraud exception. But even if there were a crime-fraud exception in Trump’s case, his lawyers could still invoke their fifth amendment right against self-incrimination if they had knowingly misled the government on his behalf.

Ultimately, the issue for the justice department is whether the attorney general, Merrick Garland, gives his approval to move ahead with an extraordinary prosecution for obstruction against the former president, and whether Garland does so against his lawyers.

If Garland chooses to take that step, federal prosecutors would probably move to find ways to compel Bobb and Corcoran’s testimony to reveal whether Trump obstructed the return of presidential records and classified materials, the legal experts suggested.

If Garland decides against pursuing an obstruction indictment, then, even though justice department investigators might seek testimony from Bobb and Corcoran anyway, they are unlikely to secure meaningful information unless it also litigates the privilege issues in court.

People close to the former president’s top lawyers broadly did not appear to believe either Bobb or Corcoran would be compelled to testify against Trump and remove themselves from the legal team. And as of Wednesday, neither had retained their own counsel, one of the people said.