Critics of the former president and his family cheered as news broke earlier in the week that New York Attorney General Letitia James had subpoenaed Donald Trump, Jr. and Ivanka Trump in the NY state civil tax fraud case against the Trump Organization and its leaders. This news came on the heels of news of a subpoena to Donald Trump himself last month.

Many news outlets, including ABC, ran incorrect headlines that Don Jr. and Ivanka “won’t comply” with the subpoenas, likely because the nation is now accustomed to seeing figures in Trumpland like Steve Bannon simply ignore Congressional subpoenas. But in fairness to the requested deponents, Don. Jr. and Ivanka aren’t ignoring the demand to appear, they have moved to quash it. What this means is that their lawyers filed papers with the court asking it to rule that the subpoenas are improper. The matter will be settled well in advance of any date set for the deposition and production of documents. A ruling on a motion to quash also will often wind up setting out the parameters of a deposition and what kinds of documents must be produced to the other side. It is not, as so much of the media reported, a wholesale thumbing of the nose at the process.

Disregard of the process is in fact what got Eric Trump into trouble in the fall of 2020 after AG James also subpoenaed him to testify in the case. As reported by the Washington Post, just two days before his scheduled appearance, Eric Trump’s lawyers abruptly canceled the deposition, refused to produce any documents showing the Trump Organization had paid the proper taxes when one of its lenders forgave a $100 million loan on the Trump hotel in Chicago, and then declined to set a new date for the deposition. AG James then went to court to force Eric Trump to appear. His lawyers cited, somewhat vaguely, his “rights afforded to every individual under the Constitution” to justify his refusing the subpoena—meaning, presumably, his Fifth Amendment right against self-incrimination. It was a curious argument because such a privilege is typically invoked at the deposition, not before it when no question has yet been asked. His lawyers also argued that the subpoena was politically motivated because it was timed to occur before the election. Finding none of these arguments persuasive, in September 2020 a New York State judge granted AG James’s motion to compel, and Eric Trump was required to testify under oath in early October of 2020.

Given this earlier ruling against Eric, are the other Trump children also unlikely to prevail? It turns out, it’s not so straightforward. It also would be a mistake to assume, as many have, that the only purpose here for the motion to quash is to delay the proceedings. After all, Eric Trump’s attempts to delay his deposition till past the election failed rather spectacularly, and it would be risky to appear to be stonewalling the case before the very judge who will decide whether, when, and to what extent you must testify and produce documents.

The gist of the matter for Ivanka and Don Jr. is instead a somewhat thorny intersection between civil and criminal law. In May of 2021, it was reported that AG James’s office had begun actively cooperating with the Manhattan District Attorney’s office on its criminal case, posting two of its own lawyers on that case and later adding to that complement. From the defendants’ perspective, this matters because the line between James’s civil action for tax fraud and the New York City DA’s criminal matter has now become now far more blurred. Because the two offices are now sharing resources and information, there are opportunities for some clever end-runs by James around the normal processes, some of which might go too far.

Take, for example, the way a Manhattan grand jury works. When it calls in witnesses to testify, it is automatic that such witnesses be granted what’s called “transactional immunity” for the testimony that they give. That means that, unless there is a specific waiver of immunity, the witness cannot be prosecuted for any crime that is the subject of their testimony. The upshot is that the Manhattan DA would likely never move to call in one of the Trump children before the grand jury, at least absent some plea deal, because it would effectively let him or her off the hook.

So how do you get the Trump children to testify under oath before the grand jury issues possible indictments against them or their fellow family members? One way is to have them deposed in a civil case, like the one AG James brought. By providing testimony under oath in that setting, there is no issue of transactional immunity. And while it’s true that they can still plead the Fifth Amendment, that doesn’t protect them as well because, unlike a criminal trial, in a civil trial the fact that a witness has taken the Fifth can be used to draw an adverse influence against the defendant as having something to hide.

James likely is fully cognizant of the lose-lose scenario under which she has put the Trump children. Also aware, it seems, are the Trump children’s attorneys. “She’s put her own people, at least four of them, in the District Attorney’s office,” Ronald Fischetti, a lawyer for Don Jr. said to reporters. “And they are talking at the grand jury. They went into the grand jury when witnesses were being briefed. They are still asking for a civil deposition so she can take the answers that she gets and give them to the Manhattan district attorney.”

In their motions to quash, the Trump children’s lawyers reportedly argued that a deposition in the civil case “is effectively the same as a deposition by the [NY District Attorney], but without providing the constitutional protections afforded every witness through the grand jury process.” They further noted, “This is a rather transparent gambit. By attempting to play both sides, Ms. James is in a position to cherry pick her investigatory methods—civil or criminal—in a calculated manner to, for example, leverage a Fifth Amendment assertion and obtain an adverse inference” in the civil investigation.

This is a non-trivial argument, and it might under the right circumstances hold up. The question now is, will a court find fault with this particular squeeze play? James wasn’t necessarily wrong to attempt it, but it won’t succeed if a court ultimately finds this to be an abuse by the AG’s office of the civil process to gather evidence for the criminal case.

The motion should be decided by the court later this month.For more political analysis, check out the Status Kuo newsletter.