Trump’s firm found guilty of fraud. He faces deeper legal waters.

Former President Donald Trump has announced that he is running for the White House again in 2024. At the same time, he is facing the greatest legal jeopardy of his life, as the Department of Justice intensifies its investigation into the potential mishandling of secret documents at his Mar-a-Lago resort.

It is impossible to predict how long this investigation will last or whether federal prosecutors will in the end decide to take the momentous step of indicting a once and possibly future U.S. chief executive. But if they do, the next two-year cycle of American politics could be a jolting journey into unexplored territory.

Trump supporters would almost certainly blast any criminal case the DOJ were to bring against the former president as political retribution by a successor from the other party. If prosecutors pass on such action, a countervailing number of anti-Trump voters may see it as a sign that he is indeed above the law, with unknown consequences for U.S. democracy.

“That’s why it’s important that the people making these decisions have a lot of experience. The answers are going to have grave consequences for our country,” says Rebecca Roiphe, a former Manhattan prosecutor and current professor at New York Law School.

A variety of legal threats

The Mar-a-Lago case is only one of Mr. Trump’s current legal problems. Under newly appointed special counsel Jack Smith, the Justice Department continues to probe whether the former president incited an insurrection, committed election fraud, or engaged in other illegal actions in connection with the Jan. 6, 2021, riot at the U.S. Capitol.

Mr. Smith, in one of his first major actions since his appointment, on Tuesday sent grand jury subpoenas to local officials in three battleground states the Trump team tried to flip following the election: Arizona, Michigan, and Wisconsin. The subpoenas asked for any and all communication between the officials and Mr. Trump, his aides, and many Trump allies.

Meanwhile, in Georgia, Atlanta-area District Attorney Fani Willis is overseeing a special grand jury that is weighing whether Mr. Trump and his allies broke state law in pushing to overturn President Joe Biden’s 2020 victory there.

And this week the Manhattan District Attorney’s office wrapped up its prosecution of the Trump Organization on 17 felony counts of tax fraud with convictions across the board.

Mr. Trump was not personally charged in the case, which accused the firm of dodging taxes by lavishing executives with unreported perks. Potential fines are about $1.6 million, a small slap for the organization. But the Trump name has now been connected to a criminal enterprise.

The former president’s company now stands “convicted of crimes. That is consequential,” Manhattan District Attorney Alvin Bragg said after the verdict.

Significance of a special counsel

Mr. Trump thus has legal exposure on a number of fronts. But in particular, the appointment of Mr. Smith, the special counsel, may have heightened Mr. Trump’s vulnerability to federal criminal charges, say some legal experts.

Mr. Smith has a reputation among some of his peers for aggressiveness. Andrew Weissmann, former lead prosecutor for special counsel Robert Mueller’s Russia investigation, tweeted this warning upon announcement of Mr. Smith’s new position: “I was described ... as a pit bull. Jack Smith makes me look like a golden retriever puppy.”

His appointment appears intended to put some substantive and political distance between Attorney General Merrick Garland and the Justice Department’s Trump investigations. In his announcement of the special counsel appointment, Mr. Garland cited Mr. Trump’s announcement that he’s running again for president and Mr. Biden’s “stated intention to be a candidate as well.”

But it is also an unmistakable sign that the government’s Trump probes are serious and charges are a real possibility. Why bother to appoint a special counsel for an investigation that is winding down?

The Mar-a-Lago case centers on whether documents, including classified government records, were illegally mishandled when Mr. Trump left the White House and moved to his Florida resort, and whether Mr. Trump and his aides obstructed government attempts to find and retrieve the papers.

Mr. Smith – former head of the Justice Department’s Public Integrity Section, and more recently a war crimes prosecutor in Europe – now has the power to decide whether to prosecute this case, as well as any high-level charges that might arise from the sweeping investigation into the Jan. 6 insurrection at the U.S. Capitol.

Mar-a-Lago is a much more straightforward investigation, and thus likely poses the most immediate danger to Mr. Trump and his aides, say some legal experts. It would be more like prosecuting a simple bank robbery or a narcotics transaction than a complex white-collar conspiracy, wrote former federal prosecutor Renato Mariotti last month.

The FBI has already confiscated thousands of government-owned documents, including dozens of secret ones, from Mar-a-Lago under a duly ordered search warrant.

“By keeping Top Secret documents even after he received a grand jury subpoena and a personal visit from the DOJ demanding their return, Trump served up a very easy case to the DOJ,” wrote Mr. Mariotti.

Higher court rulings

Last week, a federal appeals court lifted a procedural hurdle that has slowed Justice Department progress in the Mar-a-Lago case. A three-judge panel of the U.S. Court of Appeals for the 11th Circuit ruled a judge was wrong to interfere with the investigation by appointing a special master to review material seized by the FBI from the former president’s resort.

Department of Justice investigators had been blocked from following up leads provided by the bulk of the documents while the special master had conducted his review.

The 11th Circuit ruling sharply criticized federal District Judge Aileen Cannon for approving the special master in the first place.

“The law is clear,” the appeals court wrote. “We cannot write a rule that allows any subject of a search warrant to block government investigations after the execution of the warrant. Nor can we write a rule that allows only former presidents to do so.”

Mr. Trump may appeal this ruling. But lately the former president has fared badly in the Supreme Court: Late last month high court justices, without noted dissent, cleared the way for House committees to receive several years of Mr. Trump’s tax returns from the IRS.

It is far from clear whether the special counsel will indict Mr. Trump or anyone else in the Mar-a-Lago matter. It is possible that Mr. Smith will work from the bottom up, pressuring lower-level aides in an effort to strengthen his evidence. Some legal experts believe the Justice Department might wait to develop an overarching case combining aspects of Mar-a-Lago and the Jan. 6 insurrection before taking the profound step of indicting a former president. 

With the Georgia Senate runoff now concluded, the calendar is clear of possible political obstacles to legal action. But only for a short while. Given the length of time any court case against Mr. Trump would take, the Justice Department may soon be bumping up against the 2024 election cycle. 

Traditionally, the DOJ tries to avoid court actions that could affect elections for a 60- to 90-day window prior to the vote. Prosecutors would surely want to be thorough in presenting a case against the former president, and Mr. Trump would have numerous opportunities to appeal any outcome that went against him. Given that, any potential case would need to be charged by spring of 2023 at the latest, according to former federal prosecutor and Columbia Law Professor Jennifer Rogers.

Will past be precedent?

Of course, speculations about Mr. Trump’s legal troubles have proved wrong before.

The former president was not charged in the tax fraud case against his company that just wrapped up in a New York court. Last year, the Supreme Court dismissed several cases that charged Mr. Trump with violating the emoluments clauses of the Constitution and illegally profiting from his presidency.

As president, Mr. Trump was investigated by another special counsel, Mr. Mueller, over allegations his 2016 campaign had colluded with Russia and then blocked government attempts to document the connection. Mr. Mueller concluded that he had insufficient evidence to charge a criminal conspiracy in the matter.

If indicted for stolen government documents, Mr. Trump could mount a number of possible defenses, according to an extensive charging memo developed by Just Security – among them, that he had declassified all documents while president, that following his presidency he had simply followed his lawyers’ advice in retaining them, or that subordinates had acted in the case without his knowledge or approval.

The special counsel could also decide that the cases he could reasonably bring and have a good chance of winning are not weighty enough to justify the uproar they would cause.

Ultimately, Mr. Smith – and Attorney General Garland, who has the power to countermand special counsel decisions – may have a difficult decision to weigh, says Professor Roiphe.

She says they might have to look at a potential indictment and decide “which is a greater harm, the prosecution and the loss of faith and disaffection of a significant portion of the population, or letting something like this go?”

“I don’t envy their decision,” Professor Roiphe says.