Verdict in Trump Organization Trial Could Come Down to 3 Little Words

Despite all the talk of fancy apartments, free Mercedes-Benzes and cash flowing at Christmastime, the criminal tax fraud trial of Donald J. Trump’s family business could come down to three mundane words: “in behalf of.”

The company stands accused of doling out those off-the-books perks to several executives, who failed to pay taxes on them. The scheme’s architect — the Trump Organization’s longtime chief financial officer, Allen H. Weisselberg — pleaded guilty and testified at trial.

The company, however, is not automatically guilty of his crimes. Under New York law, prosecutors with the Manhattan district attorney’s office must prove that Mr. Weisselberg committed his many felonies “in behalf of” the Trump Organization, a clunky phrase that the judge overseeing the case has, in something of an understatement, called “a confusing area of the law.”

Ordinarily, when a company’s financial whiz becomes a star witness against it, things are not looking great. But if the Trump Organization has any hope of an acquittal or a hung jury after weeks of embarrassing revelations, it rests on this phrase, which has set off fierce semantic debate. The company’s lawyers have argued that the prosecution must prove thatMr. Weisselberg intended to benefit the corporation when he engineered the scheme — and that “in behalf of” can mean nothing else.

Ultimately, it falls to the judge, Juan Merchan, to decode the mystifying words. And in court on Tuesday, with the jurors absent, he appeared to agree with the defense’s interpretation.

What prosecutors will need to show, he said, “is there was some intent to benefit the corporation.”

He added, however, that prosecutors need not prove that helping the Trump Organization had been Mr. Weisselberg’s primary goal, thwarting the defense’s most far-reaching argument.

Justice Merchan is an even-keeled, gray-haired jurist who has presided over a broad array of cases, including two base jumpers who leaped from 1 World Trade Center and a man stabbed to death with a fork. This trial, however, has uniquely high-stakes implications: It has enraged the former president and his ranks of fervent supporters, and could permanently stain his family business while reverberating through the 2024 presidential campaign.

And it might all come down to four head-scratching syllables.

Already, Justice Merchan has said the company’s lawyers can tell jurors in their closing arguments on Thursday that prosecutors failed to prove that Mr. Weisselberg intended to benefit the company. And once the jurors start deliberating in the coming days, if they express confusion about the meaning of “in behalf of,” the judge may well use the defense’s preferred “intent” interpretation to clarify.

In addition to proving that Mr. Weisselberg was acting “in behalf of” the Trump Organization, New York criminal law requires that prosecutors establish that he was a “high managerial agent” of the company, and that he committed the crimes “within the scope of his employment.” Neither of those requirements is much in dispute.

But the prosecution and the defense spent weeks dissecting and debating the meaning of “in behalf of”: The company’s lawyers have called it “unconstitutionally vague,” while the prosecution argued that the defense had “misstated the law” to the jury.

Even the judge pointed out that, “This statute has been on the books for a long time, and to my knowledge this really hasn’t been argued to the extent it’s being argued now.”

There is little in New York law — or in past cases — that clarifies the meaning, Justice Merchan noted when he first addressed the issue in October. The few cases that exist were either irrelevant to the Trump trial or, in his mind, were decided in error.

And so, like anyone else, the judge resorted to Merriam-Webster. The dictionary’s website, originally cited in the defense’s court papers, suggested that — unlike the phrase “on behalf of” — “in behalf of” essentially means “for the benefit of.”

The judge also consulted various legal treatises, one of which, he said, had found that the “in behalf of” phrase “should limit corporate liability to the conduct engaged in for the corporation’s benefit and not mere personal gain.”

The debate heated up last week when prosecutors and defense lawyerslaid out their contrasting interpretations— and whether Mr. Weisselberg’s testimony helped or hurt them.

A prosecutor, Joshua Steinglass, disputed the defense’s contention that he had to prove that Mr. Weisselberg intended to benefit the Trump Organization — or show that the corporation did indeed benefit. Nevertheless, he said, there was “ample evidence of both.”

Mr. Weisselberg, for example, testified that the perks saved the company money in taxes. Mr. Weisselberg also subtracted the cost of some benefits from his overall compensation, essentially repaying the company.

Yet a defense lawyer, Alan S. Futerfas, noted that Mr. Weisselberg had repeatedly testified that he acted for his own benefit, not for the company or the Trump family. Prosecutors have not accused Mr. Trump, or anyone in his family, of taking part in the scheme.

On the witness stand, Mr. Weisselberg also admitted to betraying the company that had employed him for decades, and acknowledged that Mr. Trump did not authorize him to carry out the scheme. When Mr. Futerfas asked Mr. Weisselberg, “Were you reducing your compensation because you didn’t want to hurt the company?” He responded, “No, my intention was to save pretax dollars.”

When making his case to the judge last week, Mr. Futerfas also argued that the language of the New York law itself was so confounding that the case should be thrown out.

“All parties have struggled to determine what those words mean; particularly in the context of this case,” he said, adding that it was “very difficult, almost impossible” to ascertain what had been intended by legislators when they wrote the law in the 1960s.

Adam S. Kaufmann, a prosecutor in the Manhattan district attorney’s office for nearly two decades who oversaw white-collar cases as the chief of its investigations division, said the “in behalf of” issue seldom arose, because the actions of high-ranking officials in such cases almost always benefit a company.

“It’s not an issue that I recall seeing before,” Mr. Kaufmann said.

Lola Fadulu contributed reporting.