- Donald Trump has a decision to make on whether to testify or "take the 5th" in a civil inquiry.
- Either choice carries major risk as the former president faces criminal and civil investigations.
- Trump has said that pleading the 5th Amendment suggests guilt, but experts say it's the smart move.
Donald Trump once proclaimed himself so untouchable that he could shoot someone on 5th Avenue in New York City without facing electoral consequences.
Pleading the 5th is another matter, both legally and politically.
A Manhattan judge on Thursday ordered Trump and two of his adult children — Don Jr. and Ivanka — to sit for a deposition and turn over personal business documents in connection with New York state Attorney General Letitia James' civil inquiry into financial wrongdoing at the Trump Organization.
Trump's legal team vowed to appeal. But the ruling creates the real possibility that the former president will appear for sworn testimony about his business at a time when he is facing both civil and criminal scrutiny.
For Trump, the prospect of a deposition presents a Catch-22 as he teases another run for president.
Trump can invoke his 5th Amendment right against self-incrimination, just as his other adult son, Eric Trump, did when he was questioned by the attorney general's office in 2020. And, with a criminal investigation running parallel to James' civil inquiry, legal experts told Insider that "taking the 5th" was almost assuredly Trump's best move.
But if the former Republican president invokes his 5th Amendment right against self-incrimination, James' office could use that against him — as a so-called "adverse inference" — in the event it brings a civil lawsuit against the Trump Organization or Trump himself.
On the other hand, Trump could avoid dealing himself that legal setback and sit for a deposition. It's risky: The Manhattan district attorney's office, where investigators are also examining whether Trump improperly inflated the value of his assets to receive favorable loans, could use Trump's testimony against him.
"Any good criminal defense lawyer would advise him to take the 5th because the very same allegations are the subject of the criminal investigation, as well," said Randall Eliason, a former public corruption prosecutor who now teaches criminal law at George Washington University. "It seems from the outside that he'd have a legitimate claim of 5th Amendment privilege. That would be the smart thing to do as far as the criminal exposure."
But, Eliason added, "that is risky for the civil proceeding, because in the civil case that could be used to raise an inference against him."
The New York attorney general's civil inquiry raises the threat of steep fines for Trump and his business, so pleading the 5th could be expensive. But prison time is on the table in any criminal case, and Trump would avoid lending the criminal investigation any fodder by taking the 5th, legal experts said.
That move nevertheless carries the risk of causing substantial reputational damage for Trump, who has said that pleading the 5th is "for the mob" and only for the guilty.
"Generally, someone with potential criminal exposure is not going to willingly testify in anything. But high-profile cases are different for so many reasons. There are calculations going on that aren't just legal calculations," said Jeffrey Bellin, a former federal prosecutor who now teaches criminal law at William & Mary Law School.
Under the conventional wisdom, Bellin added, "it's hard to win an election if you've invoked the 5th Amendment because people will assume you did that because you did some kind of crime."
Trump, however, is a famously unorthodox politician who weathered allegations of sexual and financial misconduct on the way to the presidency.
As president, he navigated two impeachment trials and all manner of legal affronts involving his administration, campaign operation, inauguration committee, Washington hotel, and even mental health.
Since leaving the White House, Trump has continued to maintain a firm hold on the Republican Party.
Eliason predicted that, if Trump takes the 5th, he'll spin the move to supporters as one that he took at the instruction of his lawyers and in the face of prosecutors he has pilloried as "vicious" and "racist."
"His base will love it," Eliason said. "It just feeds into the whole victimization narrative."
Indeed, if Trump takes the 5th and runs again, it will be only the latest test of his 2016 boast that he "could stand in the middle of Fifth Avenue and shoot somebody, and I wouldn't lose voters."