Donald Trump has the nickname “Teflon Don” for a reason: Somehow, attempts to pin him down for a crime never seem to stick. One of the reasons is that Trump is very savvy about keeping himself at arm’s length from the evidence tying him to the criminal activity, often using his lawyers as a shield. That’s why the recent ruling by U.S. District Judge Beryl Howell, upheld by the U.S. Circuit Court of Appeals for Washington, D.C., ordering Trump’s lawyer Evan Corcoran to both testify Friday and turn over documents about communications with Trump is a major breakthrough for the Justice Department. Special counsel Jack Smith’s ability to pierce the attorney-client privilege may finally provide direct evidence tying Trump to obstruction of justice.
A few go-to tactics often emerge in cases involving Trump. One is his use of lawyers to do his dirty work.
A few go-to tactics often emerge in cases involving Trump. One is his use of lawyers to do his dirty work. In the probe underway in Manhattan, for example, prosecutors are looking at the hush money payments made by Trump’s former lawyer and fixer, Michael Cohen, to Stormy Daniels on the eve of the 2016 election. To charge Trump with a crime, District Attorney Alvin Bragg will have to show that Trump’s later reimbursement of Cohen, disguised as payments for legal services, violated state laws.
Another signature move for Trump is to use various kinds of privilege he may be able to assert to create a “cone of silence” that prosecutors can’t penetrate. We’ve seen him do this often with executive privilege, asserting that neither Congress nor the courts can probe conversations he had with his close advisers in the days leading up to Jan. 6, 2021. (While Trump was largely able to stonewall Congress using executive privilege, he has had limited success with this tactic in court — a federal judge recently rejected this claim and ordered several aides, including Trump’s White House chief of staff Mark Meadows, to testify before a grand jury.)
The Justice Department’s investigation into Trump’s possession of classified documents at Mar-a-Lago highlights this pattern. After several months of futile back and forth between Trump and the National Archives to retrieve the missing documents, the Justice Department served a grand jury subpoena ordering Trump to turn over all classified documents in his possession. Trump’s attorney Christina Bobb signed a certification attesting that all of the documents had been returned.
A subsequent search warrant executed at Mar-a-Lago, which turned up about 100 additional classified documents, however, revealed that certification to be false. Under questioning by prosecutors, Bobb stated that she had been instructed to sign the certification by Trump’s other attorney, Corcoran. But when Corcoran was brought in to testify in front of the grand jury, he avoided answering the prosecutor’s questions — which presumably concerned how he came to believe from Trump that all of the documents had been returned — citing attorney-client privilege.
In the law, the attorney-client privilege is sacrosanct. In order to provide the best representation they can for their clients, lawyers need to be able to have open and candid conversations with them; that, in turn, requires that clients can trust that anything they tell their attorneys in the course of representation will remain absolutely confidential. The privilege belongs to the client, and only the client can waive it. Apart from that, there are very few exceptions, but one of them is critical: the crime-fraud exception. This rule states that people can’t use their attorneys, or the attorneys’ services, to further or conceal crimes. This is the exception the special counsel asked Judge Howell to invoke to compel Corcoran to testify.
In making this motion, a rare and extraordinary step taken by prosecutors, Smith believed that Trump used his attorney to commit obstruction of justice, both by misleading him that all classified documents had been returned and by certifying Trump’s compliance with the Justice Department’s subpoena on his behalf. Breaking the cone of silence between Trump and his attorney may be the fatal blow for Trump in the Mar-a-Lago investigation. Judge Howell agreed, ruling that prosecutors had made a “prima facie” showing that justified piercing the attorney-client privilege. In making this ruling, the judge determined that prosecutors had shown by a “preponderance of the evidence” or, more likely than not, that Trump had committed criminal violations through his attorney. The judge ordered Corcoran to testify before the grand jury and to turn over notes and audio transcripts to prosecutors. Trump appealed the judge’s ruling but was swiftly rejected by the Court of Appeals. He didn’t attempt to appeal the order further, and Corcoran returned to the courthouse Friday to testify. While we don’t yet know what transpired during Corcoran’s testimony Friday, we can say that breaking the cone of silence between Trump and his attorney may be the fatal blow for Trump in the Mar-a-Lago investigation. One of the most difficult elements to prove in an obstruction of justice investigation is the defendant’s state of mind: The law requires the government to show that the defendant acted with “corrupt” intent, not by mistake or inadvertence. Without a window into a defendant’s head, prosecutors usually have to prove this circumstantially. But by testifying to conversations he had with Trump and potentially even providing contemporaneous notes and transcripts of their conversations, Corcoran is in a position to provide direct evidence that Trump knowingly lied to him that all of the documents had been returned. That can seal the deal for the special counsel — and as icing on the cake, Smith could also charge Trump with making a false statement, since his lies would have induced Corcoran to sign a false certification. One of the big challenges for the special counsel in the Mar-a-Lago case is differentiating it from the cases of other officials who have discovered classified documents in their possession. In the last few months, President Joe Biden and former Vice President Mike Pence have discovered classified documents in their possession that they were not authorized to have. (Even former President Jimmy Carter had found classified documents at his home in Plains, Georgia.) The difference with Biden, Pence and Carter is that each of them fully cooperated with the government and promptly returned the classified material to the archives. But by pulling back the curtain on Trump’s communication with his lawyer, Smith can remove Trump’s Teflon protection and demonstrate why his case is different.
Asha Rangappa
Asha Rangappa is a senior lecturer at Yale University's Jackson Institute for Global Affairs and a former associate dean at Yale Law School. Before Yale, she served as a special agent in the New York Division of the FBI, specializing in counterintelligence investigations. She has been a contributor on numerous television and radio outlets and is now a legal and national security analyst. 
