Klukowski: Donald Trump Should Appeal Unconstitutional Civil Fraud Fine All the Way to U.S. Supreme Court

Former President Donald Trump’s $464 million civil fine in New York is unconstitutional, and, for everyone’s sake, he needs to appeal this all the way to the U.S. Supreme Court, so a ruling that this victimless penalty violates the Eighth Amendment’s Excessive Fines Clause can protect all Americans going forward.

Judge Arthur Engoron — a county judge in New York’s court system — imposed the staggering so-called fraud fine on President Trump in response to New York Attorney General (AG) Letitia James’s politically driven pursuit, apparently the first of its kind both in terms of the AG’s action and the judge’s decision. The former president was facing the possibility of James seizing one or more of his iconic properties to come up with $557 million just to be able to appeal Engoron’s astounding judgment.

Fortunately, sanity prevailed on Monday when the New York Supreme Court Appellate Division — the intermediate court in the New York state court system — ruled that a $175 million bond would be sufficient to appeal. President Trump announced that he would post that bond within the ten days that the appellate court specified, allowing him to appeal the underlying $464 million judgment.

And appeal President Trump should, all the way to the U.S. Supreme Court, because this civil fraud judgment is unconstitutional under the Eighth Amendment to the Bill of Rights.

The Constitution’s Eighth Amendment provides, “Excessive bail shall not be required, nor excessive fines imposed, nor cruel and unusual punishments inflicted.” Although it has always been a criminal procedural safeguard for defendants accused of crimes, the words of the amendment do not limit it to crimes. There is no reason it could not be invoked in a civil proceeding under the right circumstances.

Principles that the Supreme Court has set forth over the years to govern the Excessive Fines Clause would apply here as well as they do any crime. As the Supreme Court has held, the Excessive Fines Clause “limits the government’s power to extract payments, whether in cash or in kind, as punishment for some offense.”

In the Supreme Court’s 2019 case, Timbs v. Indiana, the Supreme Court unanimously held that the Excessive Fines Clause applies to states through the Constitution’s Fourteenth Amendment. The reason that the Fourteenth Amendment extends this Eighth Amendment protection is because the right in question is “fundamental to our scheme of ordered liberty” and “deeply rooted in this Nation’s history and tradition.”

In fact, Justice Ruth Bader Ginsburg’s opinion for the court in Timbs traced the clause’s “venerable lineage back to at least 1215,” to the Magna Carta in England. “As relevant here, Magna Carta required that economic sanctions be proportioned to the wrong and not be so large as to deprive an offender of his livelihood,” Ginsburg wrote.

Applying the Excessive Fines Clause here is consistent with how the Supreme Court has dealt with other areas of law. For example, the Constitution sets up the federal government and state governments as co-equal sovereigns, each having authority in the areas the Constitution assigns to them. One attribute of sovereignty is the authority to pass laws forbidding things that harm society, label the acts that cause such harms crimes, and prosecute in your own court system those who allegedly commit such crimes.

From this, we get what is called Younger abstention. Named for the Supreme Court case that first announced the rule, Younger holds that when a state begins a criminal prosecution, federal courts will abstain from hearing the case even if they have jurisdiction, allowing the state court to proceed without federal interference, knowing that if there is a federal issue in the case, then after the state supreme court decides any appeal in the case, the defendant can ask the U.S. Supreme Court to review the federal issue involved.

However, Younger applies to some cases that are not criminal prosecutions. In civil enforcement actions brought by the government — not a private plaintiff — against the defendant, if the enforcement actions bear sufficient similarity to a criminal enforcement action, then a federal court will still abstain from hearing the case under Younger, leaving the parties in the state court system.

The U.S. Supreme Court should follow a similar approach here with the Eighth Amendment. There are no victims here. The financial institutions that provided financing to President Trump’s business ventures made lots of money. The allegation of fraud was made by James, who is the chief law enforcement officer in the Empire State, not any of those banks. Since it would be a gross abuse of her office to target a private citizen — which is precisely what she is doing, campaigning for office on the promise of “getting Trump” — this case does not have the basic attributes of civil litigation. Both the prosecutor and the judge are punishing Trump — a hallmark of criminal prosecution.

So the guarantees of the Eighth Amendment should protect Trump. One of those is that the Excessive Fines Clause requires any fines to be proportional. Since everyone made money here and none of the lending institutions are complaining — in fact, they made it clear in court that they are happy with the business they did with Trump — this $464 million is appallingly excessive. It shocks the conscience, which is a red line in the law.

And so the fine here is unconstitutional. President Trump may need to pursue the case all the way up the court system to get to that point, but, hopefully, between his business empire and tens of millions of supporters, he can persevere long enough for an appellate court to reverse Judge Engoron’s shameful miscarriage of justice, one that gives effect to James’s vengeful bloodlust against the presumptive Republican nominee for president.

The only reason there is no case on the books that already makes it clear that Engoron’s fine is unconstitutional is because no one has done this before. That alone is a warning sign, as the Supreme Court has made it clear in NFIB v. Sebelius and other cases, that when no one has tried something in more than two centuries, it could be an indication that what they are trying to do is not allowed by the Constitution.

It is ironic that President Trump makes the case that he wants to be president again so that he can lead the country in a different direction and, among other things, protect the American people against government officials who often appear to be working against their best interests. The irony is that on his road back to the White House as a private citizen, he is in a fight that embodies precisely those same concerns, locked in combat with an attorney general who is abusing her power in new and terrible ways.

If President Trump wins this fight — as he should — the nation will be better off as a result.

The case is New York v. Trump, No. 2024-1134 in the Supreme Court of New York Appellate Division, First Judicial Department.

Breitbart News senior legal contributor Ken Klukowski is a lawyer who served in the White House and Justice Department. Follow him on X (formerly Twitter) @kenklukowski.