Trump’s Legal Team Is Enmeshed in a Tangle of Possible Conflicts

M. Evan Corcoran, a lawyer who accompanied former President Donald J. Trump to court this week for his arraignment on charges of trying to overturn the 2020 election, has given crucial evidence in Mr. Trump’s other federal case — the one accusing him of illegally hoarding classified documents.

Another lawyer close to Mr. Trump, Boris Epshteyn, sat for an interview with prosecutors this spring and could be one of the former president’s co-conspirators in the election tampering case.

And Mr. Epshteyn’s lawyer, Todd Blanche, is defending Mr. Trump against both the documents and election case indictments.

The legal team that Mr. Trump has assembled to represent him in the twin prosecutions by the special counsel, Jack Smith, is marked by a tangled web of potential conflicts and overlapping interests — so much so that Mr. Smith’s office has started asking questions.

While it is not uncommon for lawyers in complex matters — like large mob cases or financial inquiries — to wear many hats or to play competing roles, the Gordian knot of intertwined imperatives in the Trump investigations is particularly intricate and insular.

Some of the lawyers involved in the cases are representing both charged defendants and uncharged witnesses. At least one could eventually become a defendant, and another could end up as a witness in one case and Mr. Trump’s defender in a different one.

All of that sits atop another thorny fact: Many of the lawyers are being paid by Save America PAC, Mr. Trump’s political action committee, which has itself been under government scrutiny for months. Some of the witnesses those lawyers represent work for the Trump Organization, Mr. Trump’s company, but their legal defense has not been arranged by the company, but rather by Mr. Trump’s own legal team, a person with knowledge of the matter said.

Although clients might choose to stick with their lawyers despite a conflict, just this week, prosecutors under Mr. Smith sent up a warning flare about these issues. They asked Judge Aileen M. Cannon, who is overseeing the documents case, to conduct a hearing “regarding potential conflicts” arising from the complex client list of one lawyer, Stanley Woodward Jr.

Mr. Woodward represents Walt Nauta, Mr. Trump’s personal aide and one of his co-defendants in the documents case. Mr. Woodward has also worked for at least three witnesses in the broader inquiry who could be called to testify at trial.

One of those witnesses, Yuscil Taveras, an information technology worker at Mar-a-Lago, Mr. Trump’s private club and residence in Florida, recently provided prosecutors with potentially incriminating information about Mr. Nauta after parting ways with Mr. Woodward and getting a new lawyer.

In a motion to Judge Cannon filed on Wednesday, prosecutors said that given all of this, Mr. Woodward could have “divided loyalties” and asked the judge to inform Mr. Woodward’s clients about the “potential risks” they face.

Prosecutors appear to have similar qualms about another lawyer in the documents case, John Irving, who represents Carlos De Oliveira, Mr. Trump’s other co-defendant, according to people familiar with the matter. Mr. Irving’s client list also includes three witnesses who were interviewed by investigators and could, in theory, end up on the stand.

Mr. Woodward has signaled that he will not contest the need to hold a hearing. And he and Mr. Irving, both of whom declined to comment, disclosed the potential conflicts to their clients early on, informing them that there could come a point when they would need new lawyers, according to people familiar with the matter.

In a statement, Steven Cheung, a spokesman for Mr. Trump, argued that it would be normal for the judge to hold a hearing to consider the potential conflicts, describing it as “commonplace” in such a broad case.

“There is nothing unusual or concerning about any court confirming that President Trump and others are aware of any potential waivable conflicts issues, of which they all are certainly already aware,” he said. “Any attempt to read into this or otherwise guess about the president’s legal strategy is ridiculous and sad.”

Still, the complexities surrounding the case are extensive and have raised concerns for prosecutors.

“This is boundary breaking,” Bruce Green, who teaches legal ethics at Fordham Law School in New York, said about the totality of the issues involved. “What I’m most curious about is why these lawyers want to play so many roles. Usually, lawyers just want to be lawyers.”

The potential conflicts confronting the lawyers in Mr. Trump’s prosecutions come from a variety of sources.

Some involve situations in which the lawyers could be put in the untenable position of cross-examining a former client in the service of defending a current one. Others stem from bumping up against the guardrails put in place to keep lawyers from advocating for their clients with one hand while possibly incriminating them with the other.

Then there is the issue of the lawyers’ bills largely being paid by Mr. Trump’s political action committee. That situation, said Stephen Gillers, a legal ethics professor at New York University, was theoretically not all that unusual. Organizations often foot the bill for employees who need legal representation resulting from “the scope of their employment,” he said.

Still, Mr. Gillers said, problems can arise when the entity paying the fees chooses or steers a lawyer toward a client and that lawyer has competing loyalties when it comes to the payer and the client’s best interests.

Many potential objections to conflicts in these cases could be waived by the clients or otherwise mitigated by the courts, Mr. Green said. But he cautioned that judges often lean toward avoiding conflicts at all costs — up to and including disqualifying lawyers who face them — because the consequences of allowing them to continue could result in the dismissal of the case.

One of the most awkward situations in a Trump-related case came on Thursday when the former president was accompanied to his arraignment on election interference charges by Mr. Corcoran, a lawyer who had worked with him before on both that matter and the documents case.

Mr. Corcoran’s presence in the courtroom was somewhat unexpected because five months ago a federal judge had ordered him to provide Mr. Smith with the extensive audio notes he made about his work for Mr. Trump. The recorded notes were handed over after the judge determined that Mr. Trump had likely misled Mr. Corcoran and tried to use his legal services to commit a crime — an exception to the attorney-client privilege that would normally protect such recordings.

The audio notes, in which Mr. Corcoran described assisting Mr. Trump to comply with a subpoena that demanded all of the classified materials in his possession, played a central role in the indictment that was filed in June accusing Mr. Trump of illegally retaining more 30 sensitive documents after leaving office.

The notes laid out in detail how Mr. Trump pressured Mr. Corcoran to prevent investigators from reclaiming classified material, according to the indictment, suggesting that he “hide or destroy documents called for by the grand jury subpoena.”

Prosecutors are likely to call Mr. Corcoran as a witness at Mr. Trump’s documents trial in Florida, even as he might continue to assist the former president’s defense team on the election case in Washington, people with knowledge of the matter have said. Mr. Smith’s prosecutors have inquired about Mr. Corcoran’s role in the election case, but have not yet signaled that they plan to object to it.

Although he was in court on Thursday, Mr. Corcoran has not formally appeared on Mr. Trump’s behalf in the case. And if there were a conflict, Mr. Trump could choose to waive potential objections to it. It is unclear why Mr. Trump, who prizes loyalty, would continue to want Mr. Corcoran’s assistance.

But it could be part of a long-shot challenge to the so-called crime-fraud exception that permitted the notes to handed over in the documents case.

“There is a rule called the advocate-witness rule that forbids lawyers from occupying both roles, and Trump may believe it will be easier to keep Corcoran off the stand and to exclude his grand jury testimony if he remains on the trial team,” Mr. Gillers said.

A different twist emerged on Tuesday when the election case indictment was handed up in Washington. The charges mentioned six co-conspirators who helped Mr. Trump to execute his plans. One of them — Co-Conspirator 6 — was described as a “political consultant” who assisted Mr. Trump in what has become known as the “fake electors” scheme.

While prosecutors have not identified Co-Conspirator 6, an email obtained by The New York Times suggests that it could be Mr. Epshteyn, a lawyer and strategic adviser to Mr. Trump who was paid for political consulting in 2020 and who has served throughout the recent investigations as one of his top advisers and his in-house counsel. The email’s contents and its recipient — Mr. Trump’s former lawyer, Rudolph W. Giuliani, who is Co-Conspirator 1 in the indictment — match that of an email described in the indictment as sent by Co-conspirator 6.

It would be an uncomfortable development, to say the least, if Mr. Epshteyn, who often travels with the former president and accompanied him to his arraignment on Thursday, was also an unnamed, unindicted participant in the case.

There is also the fact that Mr. Ephsteyn’s lawyer, Mr. Blanche, is a lawyer for Mr. Trump and is representing the former president not only in the two cases brought by Mr. Smith, but also in a case brought by the Manhattan district attorney. In that case, Mr. Trump has been accused of 34 felonies stemming from a hush payment to a porn actress in the run-up to the 2016 election.

Mr. Ephsteyn hired Mr. Blanche last year before any of the cases against Mr. Trump had been filed. Mr. Blanche declined to comment.

Photo credits: Jonathan Ernst/Reuters (M. Evan Corcoran); Alex Brandon/Election 2024 Pence, via Associated Press (Donald J. Trump); Amr Alfiky/Reuters (Todd Blanche); Jim Lo Scalzo/EPA, via Shutterstock (Boris Epshteyn); Lynne Sladky/Associated Press (Stanley Woodward Jr.); Doug Mills/The New York Times (Walt Nauta).