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Trump’s New York Civil Case Is A Brazen Declaration Of Lawfare

trump sitting in courtroom
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As a lawfare plaintiff, you win some and lose some — but you can make all of them hurt.


Former President Trump, his sons, and his companies are sitting on trial in a case filed by New York Attorney General Letitia James with state court Judge Engoron presiding. Pundits, anchors, and political commentators have expressed the common opinion that Donald Trump will be found “guilty” in that case — either because Trump did wrong or because the judge is biased against the Trump surname. Others have announced Trump will soon be in prison as a result of the claims pending against him in this case. There are things we can all know for certain. No one will be found guilty in that civil case, and no one will go to jail. The case is about money, not freedom. And, more so, is an open example of “lawfare” at its most destructive.

Unrestrained litigation at any cost, aka lawfare, is not a new concept but has earned recent attention due to Trump’s labeling of these cases as “witch hunts” and their high-profile and high-stakes nature. The New York case intends to fine Trump a fortune and punish him by putting his companies out of business. Team Trump’s legal bills and trial costs in this case will be measured in the many millions of dollars.

Trials are time-consuming. They are a non-physical war. In this case, there have been countless meetings, court appearances, filings, written requests for documentation, forensic accounting, depositions, oral arguments, eyewitness and expert testimony, and extensive motion practice. Everyone is on the clock.

While these are the hallmarks of most litigation, lawfare offers the party bringing the case an opportunity to win regardless of the jury’s verdict or judge’s decision — that is, if you define “win” as having caused the other side pain, treating them as an enemy, not a defendant. If the AG’s office proves its case, the state will have inflicted tangible harm on the Trump defendants by taking a massive money judgment against them. It will also have made them spend a fortune and disrupted their businesses, lives, and one of their campaigns for the highest office in the land.

If the AG loses, now or on appeal, she will be deprived of the money judgment but will still have caused plenty of wreckage. It is truly a win/win for the state, which also does not have to be concerned about paying outside counsel fees. In lawfare, unscrupulous plaintiffs and lawyers may actually relish the broader damage they cause by manipulating the process more than the trial verdict.

In practice, lawyers look to prior decided cases for guidance. Litigants whose names are associated with a seminal case that makes new or solidifies old law in their backyard have a few things in common. Their cases lasted for years, and they spent a fortune. Apply that concept to the list of novel civil and criminal charges and claims asserted against Trump in state and federal courts throughout the country. To be sure, nothing will be decided with finality any time soon, and even if his defense lawyers run the table in all of his cases, the cost to him (measured in dollars and time off the campaign trail) will be irreversible and staggering.

Practicing lawyers are bound by rules of ethics that are supposed to prohibit them from acting in a fashion that is disproportionate to the claims asserted. They are not supposed to irrationally scorch the earth without cause. So how one measures the practical harm to be caused in litigation against the legal remedy sought is important.

The AG claims Team Trump exaggerated the value of real estate to secure favorable loans and insurance rates. That’s it. Lenders rely upon their own appraisals. Sophisticated businesses decided to loan him money, all of which he repaid. And the banks are not complaining. This is the Trump defense. Yet, so far, James is winning.

Trump Fighting His Way Off the Mat

It is unusual for a court to decide a case like this on pretrial motion. Novel issues of law and disputed facts steer judges away from granting pretrial motions. Opposing experts disagree about property values and are normally evaluated for credibility in person at trial. Instead, the judge broadly accepted the state’s written rendition of the facts and opinion evidence. He determined after reading motions that the state’s experts and Trump experts were so far apart on their appraisals of properties that Team Trump must have lied and committed fraud.

The AG disregards that there is no victim such as a wronged investor or lender who wound up holding the bag on an undervalued piece of real estate. The state contends that none of this matters; that exaggerating, fibbing, or lying is wrong, and that the Trumps must be destroyed. Apparently, no expenditure of tax dollars is too much for the state to invest to punish these wrongs. The relief sought is the revocation of business licenses throughout the state of New York and fines as high as $250 million. Because it is unusual for a prosecutor to bring a civil case without a victim or cognizable harm, the AG’s motivations have been questioned, especially during her unprecedented daily press conferences.

Many conservatives are sure Judge Engoron will be reversed on appeal because he has “decided that Trump committed fraud before the trial even started.” It is his prerogative to decide the case on motion and without a trial if the law and undisputed facts warrant it. He will be reversed on appeal if he was clearly wrong to do that here.

Because Judge Engoron decided most factual and legal issues in favor of the state, in this trial he is hearing evidence to determine damages owed to the state. That is what is proceeding in New York, a damages hearing.

Before the Trumps can win on appeal, they must lose this civil trial and be tagged by the judge with a damage award. Then they have to fight their way off the mat. The intermediary state court of appeals will determine whether Judge Engoron was correct in his decision that determined liability against the Trumps.

If the court of appeals finds that Judge Engoron should not have granted the state’s motions, it will set aside his decision and any damage award. If the court of appeals does that, it is likely the state will appeal that decision to the New York Supreme Court. That court could either decline to take the case and return it to court for a second trial; could take the appeal, agree with the court of appeals and send the case back down; or could disagree with the court of appeals’ decision favorable to Trump and reinstitute the trial court’s findings. If there is another trial, Judge Engoron will again preside.

Potential Grounds for Appeal

Each of these Trump cases brings an odd claim, one that has never been brought against others in the past, or a charge that is not being pursued today against others who have mishandled documents or challenged elections, for instance. Some seek without precedent to unartfully blend civil and criminal statutes or state and federal laws. There will be extensive motion practice in all these civil and criminal cases, each of which will create potential grounds for appeal. If the cases are tried, virtually every trial generates some grounds for appeal either by the state or federal government or the defendants.

If the judge awards New York an amount of damages that would destroy the businesses, the Trumps will seek and almost certainly receive a stay of execution while a court of appeals evaluates an extensive trial court record for reversible error.

If Trump is found guilty in any criminal case, it is equally as likely that a trial court or an intermediate court of appeals will stay sentencing pending appeals. While some will claim this is special treatment, these things happen every day in routine cases and should be expected to happen in these remarkable actions.

Trump is banking on proving the judge has made so many mistakes or was so biased that the court of appeals will set aside his liability finding and any damage award. If the Trump organization is wrong, and the judge’s decisions hold up on appeal, the businesses will be ruined at least in New York. If they are correct, imagine the egg on the faces of the AG, trial judge, and legacy media.

The Show Trial is the Point

If the court of appeals reverses Judge Engoron’s decisions, the irreparable harm to the Trump family will have already been done, though. And, for many, that is the goal. Trump will have spent a fortune and sat for months in trials that some have labeled politically motivated abominations. He will be largely off the campaign trail during that period. He will have generated clips and sound bites for his chief political rival and the corporate media who aggressively report against him. Much of the damage will have already occurred regardless of future vindication. These are the hallmarks of lawfare. If your goal is to harm your opposition or enemy, a trial win is welcome, but a trial loss also inflicts noticeable pain and offers plenty of consolation.

As a lawfare plaintiff, you win some and lose some — but you can make all of them hurt.

Likeminded people have brought an unprecedented number of civil and criminal cases against the former president who is currently leading his party’s race to the next nomination by as many as 50 points. There was a long-standing unwritten rule that the government did not bring such claims against politicians of a certain echelon during a campaign out of concern they would interfere with election results and diminish the value of citizens’ votes. The American left has obliterated that golden rule for one man.

All thinking people should expect that when the gate swings the other ideological way, those supporting the current administration will feel the same desensitized wrath of reciprocal lawfare and their smiles will turn to tears. While that may sound attractive, it is unfortunate that we have digressed to a place where some politicians have decided the best way to win an election is to weaponize government, consume resources, and burn their surrogates’ credibility to keep the other guy off the ballot.

A year or so from now, Donald Trump might be a lawfare victim, lighter in the wallet, and/or an incarcerated private citizen. Or he will be the president of the United States, with a memory like an elephant, holding vast levers of power while living out a long life before appeals on any of these convictions or findings of liability fully run their courses. That should give pause to those who cannot hide their glee at the unprecedented legal onslaught.

Likely, both sides’ blood will mix on the courtroom floor at nearly immeasurable expense. Elections have consequences as does misuse of the litigation process.

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