Can Trump survive a legal ‘death of thousand cuts’? 

Former President Trump has long led a seemingly charmed life in confronting the judicial system, acquiring the borrowed sobriquet of “Teflon Don,” first attributed to New York mob boss John Gotti. Despite a pattern of abuses, including discrimination in family-owned housing complexes, the ruin of contractors left holding an empty bag in the wake of bankrupt Trump ventures and scamming the gullible through “Trump University,” Trump managed to keep the legal wolf from the door.

His fortunes before the law began to shift this year, showing that sooner or later the relentless demands of justice would catch up with him. Little by little, Trump is experiencing the ordeal of the “death of a thousand cuts” as claim after claim, indictment after indictment begins to sap his financial resources and perhaps even his political strength.

It began when the New York City district attorney secured a grand jury indictment for Trump’s role in falsifying corporate business records to conceal the payment of hush money to a porn actress. That was followed by a civil judgment against him for millions of dollars in the sexual assault case brought against him by writer E. Jean Carroll.

Then came the sequence of federal indictments by special counsel Jack Smith working with grand juries in South Florida and Washington, D.C. The Florida case, relating to Trump’s bizarre mania for hanging on to national defense secrets that belong to the government, was recently compounded when Smith secured a superseding indictment adding new counts alleging that Trump actually revealed state secrets to his cronies at his New Jersey golf club and that he procured the help of two staff members to purge video evidence of his concealment of the purloined papers. Trump evidently did not learn the lesson that proved so costly for his predecessor Richard Nixon — the coverup is often worse than the original crime.

The latest indictment contains only four counts, but they are among the most important types of crimes that can be charged against anyone: directly attacking the orderly transfer of national power and sabotaging the country’s belief in the integrity of its fundamental institutions.

Merely describing the nature of the three pending indictments — New York City business records fraud, Mar-a-Lago classified documents mishandling and 2020 election fraud — does not sufficiently convey the full jeopardy that Trump is facing (and Georgia state charges are yet to come). What counts is the number of counts. That is, juries will ultimately have dozens of individual predicates for convicting Trump for one or another crime. Conviction on any of the dozens of felony charges would, with an ordinary defendant at least, carry prison time.

While Trump has been sliced with dozens of felony charges, it remains to be seen whether any of these wounds will prove fatal either to his freedom or his political career. It is too soon to plan to see Trump dressed in prison orange.

First, what is most significant about the most recent charges is what they omit: Smith did not charge Trump with sedition, a charge that has been used successfully against several of the Jan. 6 rioters. Under the 14th Amendment, anyone found to have engaged in “insurrection” after having taken an oath to support the United States, as Trump did when he became president, is disqualified from ever again holding public office.

The elements of seditious conspiracy overlap with the disqualifying offense of insurrection: conspiring to “overthrow, put down, or to destroy by force the Government of the United States … or to oppose by force the authority thereof, or by force to prevent, hinder, or delay the execution of any law.”

Second, the proliferation of charges against Trump in at least three forums, with Georgia a potential fourth, could have the ironic effect of delaying the day of judgment in all of the cases. Any defendant has the due process right to have adequate time to prepare his defense. One could argue that, while Trump must fight a three- or four-front war, he should not be required to go into battle on any front imminently — at least until after the 2024 election. With Trump polling in a virtual dead heat with President Biden, he could win the election even while under indictment. As president, he would certainly see to the abandonment of any federal charges — the speculative issue of a “self-pardon” would never have to arise. Any pending state charges almost certainly would be suspended for at least four years.

Third, the New York charges, while not insignificant, appear to many to be relatively paltry and technical. It would not be unreasonable to conclude that a former president, who is legally entitled to lifetime Secret Service protection, should not be sentenced to prison for a “books and records” violation, even if an NYC jury eventually finds him responsible for fraudulent entries in his corporate accounts.

Fourth, while the Mar-a-Lago charges are serious, the special counsel may have made a strategic error in filing the charges in South Florida rather than in Washington. It takes only a single juror to hang the jury and prevent conviction. Trump had strong support in 2020 in the district where he is to be tried. Regardless of the strength of the evidence, Trump needs only one MAGA supporter in the jury room who accepts the drumbeat of rhetoric from the former president and other politicians that this prosecution is simply a “weaponization” of the Justice Department.

Finally, in Washington, Trump confronts an inhospitable jury pool, since he lost there overwhelmingly in 2020. He will stand before a no-nonsense judge who has dealt harshly with Jan. 6 insurgents.

But each of the four counts of the indictment is defensible on one ground or another. The various fraud theories all require proof that Trump acted “corruptly” in claiming that the election was being stolen. Although the law generally treats “willful blindness” or “conscious avoidance” of the truth as the equivalent of knowledge of the facts, it is conceivable that some jurors, even in Washington, might think that Trump’s monomania led him into sincerely believing that he was no “loser.”

Also, the Supreme Court has been skeptical about expansive prosecution theories seeking to hold public officials accountable for “fraudulently” depriving the public of proper government functioning where no financial element was at stake.

The civil rights charge under the 1870 Ku Klux Klan Act is at least debatable. While there have been some prosecutions that do not involve violent interference with the right to vote, the Supreme Court has not yet approved anything as expansive as the use of this Reconstruction Era statute to criminalize Trump’s alleged effort to steal the 2020 election by arguing that he really won and contriving to achieve that result.

Moreover, the prosecution theories run up against the limits of constitutionally protected speech and advocacy. As the indictment itself recognizes, the Constitution allows even scoundrels space to make outlandish claims, sometimes even false ones, especially in the political arena. What is certain is that any conviction at the trial level will be subjected to years of appeals, potentially ending up before a Supreme Court stacked with conservative justices.

Trump may be wounded. But he has shown remarkable resiliency throughout his much-tainted career. He may stagger through all of this.

Philip Allen Lacovara is the former deputy solicitor general of the United States, counsel to the Watergate Special Prosecutor, and president of the District of Columbia Bar.