The legal irony of Trump’s seemingly endless litigation tactics

Trump is a notoriously difficult and frustrating client. But there's a logic to his strategy that could lead to his true and terrifying goal.

Donald Trump leaves a rally in Rome, Ga., in 2020, when he was still president.Brendan Smialowski / AFP - Getty Images file
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As the weeks go by, Donald Trump continues to increase his legal exposure through more and more federal and state indictments. The rate of new cases has arrived alarmingly fast. Trump’s most recent addition to his audit of damning cases: special counsel Jack Smith’s indictment Tuesday of Trump on four new counts.

Tick-tock goes the litigation clock. The question: Can the twice-impeached, thrice-indicted (at least for now), one-term, disgraced ex-president Donald J. Trump run out the clock on his myriad cases and trials, both civil and criminal?

He is actually creating heightened criminal exposure for himself while simultaneously creating credible support for his arguments for a delay in proceeding to trial.

There is a very real potential scenario in which the answer is yes, he can. And the irony is that because Trump is a gold medal crimer and does not cease in his persistent criming, he is actually creating heightened criminal exposure for himself while simultaneously creating credible support for his arguments for a delay in proceeding to trial. For law-abiding citizens, it doesn’t make sense to reward an alleged criminal with the benefits of delay, but unfortunately, that is sometimes how trial scheduling works: the more, the messier — and, as Trump and his legal teams undoubtedly hope, the better.    

To better understand what’s at stake, here’s a snapshot of Trump’s cases currently set for trial:

  • Trial date: Oct. 2, 2023 — New York Attorney General Letitia James’ $250 million civil lawsuit against Trump, Ivanka Trump, Eric Trump, Donald Trump Jr., the Trump Organization and former Trump Organization CFO Allen Weisselberg. This case involves allegations of fraud through over inflation of assets and will proceed in New York state court.
  • Trial date: Jan. 15, 2024 — After securing a $5 million jury verdict against Trump for defamation and sexual battery, writer E. Jean Carroll then secured a trial date for her original defamation claims against Trump. In this New York federal court case, Carroll seeks at least $10 million in damages.
  • Trial date: Jan. 29, 2024 — This New York civil federal class action lawsuit against Trump, Eric Trump, Donald Trump, Jr., Ivanka Trump and the Trump Organization alleges that the defendants helped promote a multi-level marketing pyramid scheme that conned victims out of their money. (As an interesting sidenote, the plaintiffs are represented by Roberta Kaplan, who also represents E. Jean Carroll.) 
  • Trial date: March 25, 2024 — Manhattan District Attorney Alvin Bragg will proceed to a jury trial in New York state court on 34 felony counts of falsification of business records against Trump. This was the first criminal indictment of a former or current president of the United States.
  • Trial date: May 20, 2024 — Trump’s latest federal indictment and the first brought by special counsel Jack Smith. Following a superseding indictment filed in Smith's classified documents investigation, Trump faces a total of 40 felony counts for wrongful retention of classified materials, as well as conspiracy to obstruct justice and making false statements. This case also includes Walt Nauta and Carlos De Oliveira as Trump’s co-conspirators.

Since these are only the cases that have been set for trial by their respective judges, this list is by no means exhaustive. It does not include all of Trump’s pending cases, such as the lawsuit brought by Rep. Eric Swalwell, D-Calif., against Trump for his role in the Jan. 6 insurrection, lawsuits brought by some of the U.S. Capitol Police officers for their injuries sustained on Jan. 6, 2021, and several other cases. 

In my opinion, special counsel Smith’s Tuesday indictment of Trump is so far the most consequential case to be brought against him. And charges may become even more dire for Trump with Fulton County (Ga.) District Attorney Fani Willis’ prosecution of the former president and his supporters for their efforts to overturn the results of the 2020 presidential election. (“The work is accomplished,” Willis told an NBC affiliate during a back-to-school event last weekend. She said she'd announce charging decisions by Sept. 1. “We’ve been working for two-and-a-half years. We’re ready to go.”)

But how will the addition of this new major case affect the timing of Trump’s present trial schedule? The nature of the charges in this newest indictment combined with what I reasonably anticipate will be a lengthy witness list and large amounts of discovery, will certainly lead Trump to argue for a trial date months and months out, assuming they even acknowledge that a trial date should be set in the first place.

The obvious common denominator for all of these cases is Donald Trump himself, as either the only defendant or one of several co-defendants. Trump is a notoriously difficult and frustrating client, often ignoring advice and counsel from his lawyers not to talk about cases or investigations, and lashing out, sometimes in violent and threatening language, against litigants, prosecutors, opposing counsel and witnesses. There are also the lawyers left in the dust who have complained of Trump’s nonpayment of their fees and other costs. Even more notably, Trump has struggled to retain attorneys to represent him because of their subsequent problems with their law licenses, disciplinary proceedings and their ability, post-Trump, to practice law now being in jeopardy.  

As we have also seen, Trump does not always attend his civil trials, as in E. Jean Carroll’s recent defamation and sexual battery case. And there are no guarantees he will actively participate in the preparation of his defense in the months and weeks leading up to trial. Customarily, all parties to litigation should work closely with their counsel to consider the issues, prepare their cases, review witnesses and so forth. This kind of preparation is especially important and critical in criminal cases, in which liberty is at stake. Such preparation would include events that Trump may not want to voluntarily attend and participate in, such as depositions and settlement conferences and pretrial hearings. Now having several cases that have been set for trial, along with several cases that are still in the discovery process, Trump is facing, logically and practically, a frenetic and hectic demand on his time, energy and resources.

Trump is a notoriously difficult and frustrating client, often ignoring advice and counsel from his lawyers not to talk about cases or investigations, and lashing out, sometimes in violent and threatening language.

Of course, Trump could simply drop out of the running and focus on his massive litigation. But if he were to do so, then he would walk away from what is likely his true goal in delaying trial: getting re-elected to the Oval Office and eliminating prosecutors’ ability to prosecute criminal cases against him and creating obstacles to civil plaintiffs from getting their day in court in a timely fashion.

Another critical factor when it comes to Trump’s attempts to delay going to trial in any of his pending cases is the notion of whether federal cases trump (no pun intended) state cases in terms of priority. There can be a perceived struggle over whether a federal case has more importance over a state case. That struggle can be illusory. But a very real consideration by a state court judge in determining whether to assert priority in trial order sometimes does involve whether the other trial is a federal case. 

Delay usually benefits the defense, so it’s only logical that Trump would pursue delay. Another consideration is that different jurisdictions are at play in Trump’s myriad of cases. Depending upon the circuit, there may be sufficient judicial resources to support a faster trial prep schedule. However, fewer judicial resources could militate in Trump’s favor in his delay gamesmanship.

Another possibility to complicate Trump’s legal life is a superseding indictment, like the one filed on Thursday in the classified documents case. That superseding indictment was a delay boon of sorts for Trump because it added new counts against him, as well as another co-defendant in Carlos De Oliveira. With the implication of the Classified Information Procedures Act, the existence of two co-defendants in this case with their own criminal exposure, and the claims by Trump that the case involves “novel issues of law” that have reportedly never been tested in the courts, the chances this classified documents case proceeds to trial in May are even less probable now.

Trump will continue to rack up more and more cases. If he fails to regain the Oval Office, then he will be tied up in litigation and trials for years to come, and there’s a chance that his trial prep may occur from inside a prison cell.

As Chinese philosopher Sun Tzu once said: “The wheels of justice grind slow but grind fine.” But if Trump throws enough sand into those gears, then he could run out the litigation clock and say goodbye to accountability for his high crimes and misdemeanors — and felonies.       

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