Donald Trump has sued or been sued some 4,000 times. He ought to know more than many lawyers how to win a lawsuit. Yet, he and his lawyers consistently violate every guideline regarding successful lawsuits. There are only guidelines, because a litigant can do everything right and still lose. Just like a litigant can do everything wrong and still win. But, the guidelines help.

$355 Million Mistake

Donald Trump was assessed a civil penalty of $355 million for civil fraud. With pre-judgment interest, that amount will exceed $400 million. That is a huge loss. And, he and his family committed huge, avoidable mistakes. Eric, Don, Jr. and Donald, Sr. all testified poorly. They were clearly not well-prepared for their testimony. Often, when major witnesses are not well-prepared, it is because they refused to meet with their lawyers and engage in the necessary amount of practice time. Just like football players practice plays over and over, so should a major witness practice his/her testimony until he is comfortable with the expected questions.


When Don. Jr. testified, he was relaxed and making jokes from the witness stand. That suggests he was too relaxed and over-confident. in his 92 page ruling, Judge Engoron said this about Don, Jr.’s testimony:

“Trump, Jr. then testified that he does not know the details of how or why [CFO] Weisselberg ended his employment relationship with the Trump Organization, which this Court finds entirely unbelievable.”

Don Jr. evaded questions he did not have to evade. He probably did not understand the implication of many of the questions posed to him. But, he or his lawyers had to know he would very likely be asked about the former Chief Financial Officer, Allen Weisselberg. That should have been easy preparation.

Lack of Preparation

Regarding Eric Trump, the Judge had several negative comments about his credibility. Such as:

“Eric Trump’s credibility was severely damaged when he repeatedly denied knowing that his father ever even compiled an SFC that valued his assets and showed his net worth “until this case came to fruition.”

Here, Eric simply strained credulity in denying knowledge of a fact about which he had to know. He had to know that the company prepared Statements of Financial Condition and that those SFC’s would be the subject of many questions. Eric was the primary point of contact for persons doing appraisals of some of the Trump properties. Contemporary emails showed Eric and Don Jr. having final review of the SFC’s. It looks like Eric did not have a good understanding of what the evidence already entailed. He perhaps assumed he would not be sad about SFC’s? In a lawsuit that was deeply focused on all renditions of property value? Someone was clueless in preparing to testify. It is pointless to deny something which is so easily shown. Eric rolled the dice with his credibility and lost.

Donald Sr.

Then, of course, the rambling answers of Donald, Sr. His campaign speeches from the witness stand. His frequent out-of-court attacks on Judge Engoron and his staff all engender dislike by the fact-finder. It is Litigation 101 to not offend or insult the court staff. Many young lawyers adopt a snarky attitude toward the staff when the clerk makes a clerical error. It is near suicide to attack the court staff for any reason. It is obvious to this author that Donald Trump did not listen to his lawyers. As trial lawyers, we all tell our clients to always extend courtesy to court room staff and to the Judge.

Donald Sr.’s frequent lapses in memory also detracted from his testimony. All three Trumps had a distinct lack of memory …. until they were shown contemporary documents. As the Judge said in his Judgment:

“[Donald Trump, Sr.’s] refusal to answer the questions directly, or in some cases, at all, severely compromised his credibility.”

Clearly, they did not practice answering questions with their lawyer about those documents. The Trumps might have still lost even if they had practiced their testimony. The Judge at one time said there was ample evidence of fraud. Heck, the Judge even granted summary judgment on the question of liability. It is very rare to grant summary judgment in a civil fraud case. But, as the guidelines suggest, the Trumps’ chances would have increased if they had simply done their homework.

See AP news report about that judgment in New York v Donald J. Trump here.