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Trump's latest lawsuit against Letitia James is rich, even for Trump

It doesn’t take a legal scholar to know that Trump’s latest lawsuit is a mess. Here’s a professional explanation anyway.
Photo illustration: Images of Letitia James speaking and Donald Trump speaking on stage pointing to the left.
Attorney General Letitia James hasn’t seemed phased by Donald Trump’s latest avoidance tactics.

In yet another transparent move to deflect and delay, former President Donald Trump, along with the Trump Organization, on Monday filed a lawsuit in a New York federal court against New York Attorney General Letitia James, alleging that her pending and very active investigations into Trump and his company’s business practices are politically motivated and violate his constitutional rights.

In bringing this lawsuit, the hypocrisy is quite rich, even for Trump.

Breathing life into a well-worn party line, Trump publicly complained that James’ legal maneuvers were just a continuation of the various political “witch hunts” from which he has long suffered. In response, James swiftly issued a news release declaring that “neither Mr. Trump nor the Trump Organization get to dictate if and where they will answer for their actions. Our investigation will continue undeterred because no one is above the law, not even someone with the name Trump.”

The lawsuit was filed by one of Trump’s newest attorneys, Alina Habba, whose small New Jersey practice certainly does not fit in the category of the Big Law firms that have typically represented Trump and his family business. According to The Washington Post, Habba’s prior experience includes serving as general counsel to a parking garage company and representing a former cast member of “The Real Housewives of New Jersey.” That Habba graduated from law school in 2010 just feeds the flames of critics who believe that Trump can no longer retain high-profile, powerhouse attorneys to represent him in the myriad litigation in which he is constantly mired.

The latest lawsuit brought by Trump and the Trump Organization seeks declaratory and injunctive relief and asserts four counts against James “in her officially capacity as Attorney General for the State of New York”: violation of the 14th Amendment, violation of the First Amendment, violation of the Fourth Amendment and abuse of process. Trump demands a jury trial but in the interim requests that the court order that James “immediately cease, or, at a minimum, appropriately limit all ongoing investigations of [Trump and the Trump Organization] pending resolution” of the lawsuit. To get that temporary injunction, though, Trump will have to, among other things, convince the judge that he has a likelihood of success on the merits of his claims. Injunctive relief is an extraordinary remedy left up to the discretion of the court, and based upon a review of his lawsuit, Trump will never be able to satisfy the necessary elements to achieve an injunction barring James from continuing her investigation.

In bringing this lawsuit, the hypocrisy is quite rich, even for Trump. In the first paragraph of the complaint, Trump quotes James when she declared in her news release, “No one is above the law.” But it doesn’t take a legal scholar to know that the grounds for Trump’s lawsuit is to try to prevent his deposition from moving forward on Jan. 7. James publicly announced a few weeks ago that Trump’s deposition was to be taken on that date as part of her office’s civil fraud investigation into the valuation by the Trump Organization of certain assets, including several real estate properties.

Trump aggressively filed a lawsuit that most legal experts believe is baseless, frivolous, and ultimately will be unsuccessful.

Trump has tried on prior occasions to stop James, by filing motions to block the release of documents that her office subpoenaed, and he has lost each time. Instead of simply filing a motion for a protective order to prevent his deposition from moving forward (which one of his other lawyers has said he will do), Trump aggressively filed a lawsuit that most legal experts believe is baseless and frivolous and ultimately will be unsuccessful.

Trump’s real danger and exposure will arise once he is forced to sit for his deposition in James’ investigation. There is a parallel criminal investigation being conducted by Manhattan District Attorney Cyrus Vance into whether the Trump Organization fraudulently submitted false property valuations for purposes of lending and tax breaks. James’ office is working with Vance’s office, and there is distinct and clear overlap in terms of focuses of the investigations, the evidence gathering, etc.

Vance also intends to depose Trump on Jan. 7. However, Trump, whether through advice of counsel or of his own survival instincts, would likely have to assert his Fifth Amendment right against self-incrimination during the deposition by Vance. To properly assert his Fifth Amendment right, he would have to respond in the same manner to individual questions as they are posed to him; he could not make a blanket assertion that he is refusing to answer any questions based upon that constitutional right. If Trump is criminally charged — he has not been accused of wrongdoing so far — then the prosecution could not use his invocation of his constitutional right against him.

To be clear, the Fifth Amendment right is one that is personal to the individual; a corporation or its records are not protected by the Fifth Amendment. So the Trump Organization finds itself in an even more precarious situation.

For James’ deposition questioning, Trump could choose to answer her questions under oath. But, if he elects not to do so and he asserts his Fifth Amendment right against self-incrimination, then a jury would receive an instruction that Trump refused to answer questions, and an adverse inference would be imposed against him regarding his silence in the face of probative evidence. In a civil case, if a party elects to invoke their Fifth Amendment right against self-incrimination, then a jury instruction is read to the jury by the judge allowing the jury to infer that the reason why that party isn’t speaking is because there is something negative that they are trying to hide. It is a powerful tool to be used by the opposing party because jurors usually look to the judge with deference. Were the judge to provide this jury instruction, jurors would be allowed to consider the “why” behind Trump’s silence. The end result wouldn't be pretty for Trump.

Whether he has a more solid legal plan in mind, we’ll have to wait and see. But as things stand, Trump’s tactic of filing this lawsuit against James to try to delay or prevent his deposition from occurring reeks of desperation and is certainly no guarantee of derailing James from barreling full steam ahead with her investigations.