Tips for Questioning Trump Under Oath — From Someone Who’s Done It

Donald Trump is set to take the stand Monday in a blockbuster civil fraud trial against him and his company. But it won’t be the first time he’s fielded questions under oath in a high-stakes legal battle while simultaneously running for president.

On June 16, 2016, as he was wrapping up the fight for the Republican nomination, Trump was questioned as part of a lawsuit against celebrity chef Geoffrey Zakarian. The episode was part of the fallout from when Trump launched his campaign by ranting that Mexican immigrants were rapists and drug dealers; after Trump’s remarks, Zakarian backed out of the deal he had to lease restaurant space in Trump’s forthcoming hotel in Washington D.C. Trump promptly sued Zakarian’s company for breach-of-contract — seeking $10 million — and Zakarian counter-sued.

Deborah Baum, global head of litigation at Pillsbury Winthrop Shaw Pittman, represented Zakarian in the lawsuit and was tasked with going head-to-head with Trump in a deposition.

In an interview with POLITICO Magazine, Baum offered some wisdom from her time tangling with Trump. The former president and his family are accused of fraudulently inflating Trump’s net worth in a case that could upend his New York businesses. And Trump won’t be testifying voluntarily on Monday: He’s being called as a witness by New York Attorney General Tish James to answer questions about financial documents that exaggerated the value of his real estate assets.

Baum’s advice for pinning down Trump is relatively unsurprising for anyone who’s seen him in the Oval Office or on the campaign trail: Flatter him, and give him the mic.

“Just let him talk,” she said. “I got exactly what I wanted by letting him talk.”

Trump can be slippery and obstinate, as evidenced by the deposition clips showcased in this “Full Frontal with Samantha Bee” segment where the host cheekily suggests Trump can’t read. But ultimately, a one-on-one interrogation presents him with extraordinary risks.

This conversation has been edited for length and clarity.

Betsy Woodruff Swan: Trump is notorious for speaking off-the-cuff and making outlandish claims in media interviews and rallies. Was he more cautious when he was under oath?

Deborah Baum: Not really. He was totally unprepared.

They were suing our client for over $10 million in damages for lost profits over this lease. The lease is in the middle of the whole thing. He testified that his son came to him and told him, “We just signed the lease.” And then I showed him the lease, with his signature on it: “Is this your signature?” He said, “Yeah that’s my signature.”

He had just talked about how one of his kids came to him, “We signed it.” It’s the document at the middle of their case and he wasn’t prepared enough to know that he’d in fact signed it.

Swan: What tactics does he use to evade questions he doesn’t want to answer?

Baum: I asked him to read a particular provision of the lease. He said, “Oh this print is very small. I don’t have my glasses with me, I can’t read it.” And so I said, “Well you know what, it is small. We’ll come back to this. I’ll just take this and have a copy blown up to make it bigger so you can read it.” That was one.

Swan: What is the best way to pin him down?

Baum: Just let him talk. 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. 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.”

Swan: What advice would you give the New York attorney general’s team?

Baum: You’d have to ask questions from the right direction and do it in a way so that he doesn’t know where you’re going with it.

Don’t be confrontational. I had looked at a number of transcripts of depositions of his beforehand, and people were very combative with him, and he was combative right back. And so I had a very friendly conversation with him and his lawyers before we went on record and chatted about his kids, and things like that. It was all done in a very friendly tenor, and I got exactly what I wanted.

The man responds really well to flattery. You flatter him and he’s your best friend.

Swan: How badly could Trump hurt himself on the stand if he isn’t careful?

Baum: You can certainly hurt yourself. You can blow your whole case if you’re not careful on the stand in trial. One line can blow your whole case.

They fought not to have him deposed in our case. They moved for a protective order. They demanded that we withdraw the deposition notice and said they would move for a protective order if we didn’t withdraw it. I said, “Fine, go for it.” They moved for a protective order and said we were harassing him and all that. And the judge disagreed, and we got to take his deposition in our office. When we finished the deposition, [Trump] said, “We should not be fighting with Debby. Why don’t you all stay and try to work it out?”

Swan: How did things end up for your client?

We settled. But unfortunately I can’t say more than that. The settlement is confidential.