It was a weak case, at best, for two reasons. First, it was politically motivated. James had run for office on a platform of pursuing Trump. “We will all rise up and resist this man,” she once told a campaign crowd, “and ultimately, we’ll bring him down.” Second, the trial revealed, in the words of this newsletter, “that there were no victims, that the loans were paid back in a ‘timely and total’ fashion, that the lending institutions made the loans based not on Trump’s representations but on their own research, and that some of those institutions were eager to do business with Trump again.” The suit should never have been brought, but even after James decided to go ahead, any penalty should have been small.

James structured the suit so that Trump would not have the right to a trial by jury. Instead, the case was decided by New York Judge Arthur Engoron, a longtime Democratic donor who found Trump guilty and threw the book at him. Engoron ordered Trump to pay $355 million in penalties, plus another $100 million or so in interest. The amount Trump owed would grow by the month, even if Trump appealed the case. It is now approaching $500 million as Trump’s appeal makes its way through the New York appellate courts.

It was an insane penalty, of course. And now there are indications that some judges on the court that is considering Trump’s appeal might agree. During oral arguments Thursday, a number of members of the five-judge panel expressed doubts about James’s case and Engoron’s penalty. The following is compiled from a number of press reports.

Justice David Friedman pointed out that this suit, involving the Trump Organization and such major institutions as Deutsche Bank, was not a case of a slick financial player cheating a naive victim out of money. “It hardly seems to justify bringing an action to protect Deutsche Bank against President Trump, which is what you have here,” Friedman told the state’s lawyer. “You have two really sophisticated players in which no one lost any money.”

Another judge, Justice Llinet Rosado, remarked that the transactions at the heart of the case had “little to no impact on the public marketplace.”

Another member of the panel, Justice Peter Moulton, said, “The immense penalty in this case is troubling. “How do you tether the amount that was assessed by [Engoron] to the harm that was caused here, where the parties left these transactions happy?” At another point, Moulton said, “There has to be some limitation in what the attorney general can do in interfering in these private transactions … where people don’t claim harm.”

Finally, yet another judge, Justice John Higgitt, suggested that even if there was a conflict of some sort between Trump and his lenders, “What’s being described sounds an awful lot like a potential commercial dispute by private actors.” Higgitt also wondered whether there should be any legal “guardrails” to keep James from “going into an area that wasn’t intended for her jurisdiction.”

That was a lot of skepticism, and it does not bode well for James. But it should be noted that judges ask a lot of questions of both sides, and it might be that some or all of them uphold James’s lawsuit. The court can choose to affirm the whole thing or reduce the penalty or throw it all out. 

But there’s no doubt the appeals court argument was a good day for Trump. The James lawsuit was squarely aimed at destroying Trump’s business empire. Even with all of her anti-Trump animus, James couldn’t figure out how to charge Trump with a crime, so she settled for trying to bankrupt him. She found a willing judge to make it happen. Now, we’ll see if the damage they did survives judicial scrutiny.