Legal experts warned that former President Donald Trump faces significant risks when he takes the witness stand at his New York civil fraud trial on Monday.
Former acting Solicitor General Neal Kaytal said the ex-president will face a "Hobson's choice" to either answer questions or invoke his Fifth Amendment rights.
“Both are a problem,” Kaytal told MSNBC, given that Trump is “known for giving meandering testimony," but legally speaking, his reticence could be understood “to be the absolute worst.”
“The case for [Trump] taking the Fifth Amendment is he’s basically going to perjure himself one way or another if he takes the stand,” Kaytal added. “I can’t imagine having a client like this."
Former federal prosecutor Andrew Weissmann agreed that it “will be extremely hard for him to come up with a consistent theory that’s not going to get him into a lot of trouble.”
“He’ll be forced to answer strategically because if he doesn’t answer, this whole case is over,” Weissmann added.
Former federal prosecutor Jennifer Rodgers predicted "fireworks" at Trump's court appearance.
"Trump is famously undisciplined as a speaker. He is furious about this case," she told CNN.
"He's been talking, of course, at length about how the judge is out to get him and the AG is out to get him," she continued. "So the question is, I don't know that he'll just be smug. I mean, he may explode tomorrow."
"So one question is, if it goes poorly on direct tomorrow with the attorney general's staff questioning him, will his lawyers cross-examine him, quote-unquote, cross-examine him to try to rehabilitate him in the eyes of the judge?"
Former Nixon-era White House Counsel John Dean, in conversation with CNN anchor Jim Acosta on Sunday, argued that the amount of trouble Trump could land himself in during the hearing is "infinite."
It's "not only what he says, but the way he says it is going to play out in this testimony. What he says is going to affect the judge and how he deals with the case. As you said, he's already found liability," Dean said, referring to how New York Supreme Court Judge Arthur Engoron has already found the Trump family and company liable for persistent fraud. "They're really looking at the other counts and potential damages that could be assessed against the Trump Organization."
"So, his testimony can influence that," Dean continued. "But also the theater of it, and the way he handles himself is going to have a political impact. People don't like witnesses who try to get nasty with judges. Maybe a few hard-right radicals might, but the general public does not. So, I think he's got to behave himself as well tomorrow."
Acosta then asked Dean to explicate what happens if Trump commits perjury, and whether he could be prosecuted for lying.
"He certainly could be, and it would be a question of how far out he goes, how far he reaches, how disported he gets," Dean replied. "And Letitia James, the attorney general who brought this civil action — and it could have been brought as a criminal action, but she decided to proceed in a civil matter. She can certainly initiate a perjury charge against anybody who does perjure themselves in the civil case. These are rare, but Trump creates the rarities, if you will. And if he gets way out on a limb and fabricates beyond belief, I think she might bring him up short and let him know."
CNN legal analyst Norm Eisen told Acosta that he doesn't expect Trump to "take the Fifth."
"He'll be flushing this case down the toilet if he says the word 'self-incrimination.' Unlike in a criminal case where you don't get to argue that to a jury, Judge Engoron — no fan of Donald Trump already — can draw an adverse inference if Trump takes the Fifth. He can say, 'Well, that settles it, I'm ruling against him.' Trump & Company are playing for an appeal. They know they're going to lose in front of this judge. They don't want to mess up the appellate record with the Fifth Amendment. I don't think he's going to do that," Eisen said.
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Attorney Deborah Baum, in a Politico article published Monday, offered advice for how to question Trump after she in 2016 deposed the former president in a civil suit he filed against celebrity chef Geoffrey Zakarian.
"Just let him talk," Baum told Politico, adding that Trump was "totally unprepared" for her line of questioning. "I got exactly what I wanted by letting him talk."
"In that particular case, there were some legal issues we were dealing with in terms of the likelihood or the certainty of their losses as a result of the restaurant leaving, and they claimed millions and millions of dollars of lost profits," she said. "And there’s a legal principle that your damages have to be reasonably certain to recover them. And a lot of their damages were based on how well they expected the restaurant to do. But he testified to exactly what I wanted, which was, 'With a restaurant, you never know what you’re going to get. You never know.'"
"The man responds really well to flattery," Baum added. "You flatter him and he’s your best friend."
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