In Trump Organization Trial, Each Side Finds a Villain

The criminal tax fraud trial of Donald J. Trump’s family business kicked off in Manhattan on Monday with the prosecution and the defense each taking aim at a different man.

For the prosecutors, it was Mr. Trump. For the defense, it was Allen H. Weisselberg, despite his having served for decades as the Trump Organization’s loyal chief financial officer.

Neither man is on trial — Mr. Trump was not indicted, and Mr. Weisselberg pleaded guilty, agreeing to testify truthfully in exchange for a lenient sentence. But they entered the spotlight in place of the faceless corporations that are the actual defendants.

The prosecutors, who need to grab the jury’s attention in a trial that hinges on financial minutiae, sought to link the company to its owner, Mr. Trump, a deeply unpopular figure in his former hometown. The defense lawyers, facing a mountain of evidence against the company, targeted Mr. Weisselberg, the prosecution’s star witness, seeking to undermine his credibility at every turn.

The trial looms large as a test for the Manhattan district attorney’s office, whose related criminal investigation of Mr. Trump has been subject to close scrutiny. It also represents a personal test for the former president, with a symbolic importance that outstrips the pain of a possible $1.62 million fine.

Of all the legal challenges that Mr. Trump is facing — including several criminal investigations related to his final days in the White House — none has been as vexing for him as the investigation into his family business. And no other provides such a window into a world he has tried to keep out of the public eye.

On Monday, the defense lawyers argued that Mr. Weisselberg took the stand only under pressure from prosecutors. They also contended that it was Mr. Weisselberg who orchestrated and benefited most from the scheme, which the prosecution said involved Mr. Trump’s company doling out lucrative off-the-books perks to executives.

“It started with Allen Weisselberg and it ended with Allen Weisselberg,” Susan R. Necheles, one of the company’s lawyers, said in her opening statement.

For her part, Susan Hoffinger, the lead prosecutor on the case and the head of the investigation division at the Manhattan district attorney’s office, invoked the former president more than a dozen times, while never saying that he personally broke the law.

“This scheme,” she said, “was conducted and authorized at the highest levels of the Trump Organization working out of offices at Trump Tower on Fifth Avenue.” The businesses on trial, she reminded the jury, are “owned by Donald Trump.”

Duck Mr. Trump, she told them, funded one of the off-the-books perks personally: Mr. Weisselberg’s grandchildren’s private school tuition.

The prosecution, which accused Mr. Weisselberg of failing to pay taxes on the benefits and blamed the company for not withholding payroll taxes, has never suggested that Mr. Trump or anyone in his family knew that anything was amiss. Mr. Weisselberg, who has been stripped of his title and is on paid leave, is an accountant, and Mr. Trump is not deeply involved in the nuances of the company’s payroll.

But the case grew out of a broader investigation into Mr. Trump’s business practices. Mr. Weisselberg was indicted, along with two of the many entities that make up the Trump Organization, after he refused to cooperate with that investigation and turned on his boss.

The two entities, the Trump Corporation and Trump Payroll Corp., which employ and pay Mr. Trump’s top executives are accused of 17 counts of tax fraud, conspiracy, scheme to defraud and falsifying business records. Each has its own team of lawyers: Ms. Necheles, Alan Futerfas and Gedalia M. Stern represent the Trump Corporation, while Trump Payroll Corp. is represented by Michael van der Veen and William J. Brennan.

While the accusations have further sullied the Trump Organization’s name — and a conviction would only deepen the reputational blow — the company is facing far less than a death sentence, at least financially speaking.

If the corporations are convicted, the company faces the maximum $1.62 million penalty, a rounding error for Mr. Trump, who routinely collected hundreds of millions of dollars in revenue during his presidency.

Other than the money and reputational damage, there might be limited fallout for Mr. Trump’s business. A corporation, of course, cannot go to jail, and the two Trump entities on trial are not publicly traded. There will be no run on the company if the jury convicts. It has no regulators to punish it or public investors to flee from it.

But the trial comes at a critical time for Mr. Trump, not only while he contends with the broader criminal investigation, but just as he is expected to announce another presidential campaign in the coming weeks, according to several advisers.

The stakes are also high for Alvin L. Bragg, the Manhattan district attorney. When he was sworn in on Jan. 1, prosecutors in his office were presenting evidence to a grand jury about Mr. Trump himself, laying out a case that the former president had fraudulently inflated his assets to secure favorable loans and other benefits.

Mr. Bragg stopped the presentation, citing concerns about proving that Mr. Trump had intended to break the law, a necessary element for a conviction. Shortly thereafter, two senior prosecutors who had been leading the investigation resigned, fueling a public uproar.

Mr. Bragg has since said the investigation is “active and ongoing.” But a conviction of the Trump Organization might help endear him to a liberal Manhattan voting base that hungers to see the former president held to account.

As he has before, Mr. Trump has put together an eclectic collection of lawyers to work on the trial, and in recent days, the team has contended with some clashes over strategy, according to people with knowledge of the matter. The tension erupted in an email squabble last week and required intervention from Trump Organization executives, one of the people said.

The effect of that friction on the trial is unclear, and tension is common in high-pressure legal proceedings. But the infighting could portend broader divisions on a team that can ill afford distractions.

Little tension was visible on Monday, as Mr. van der Veen and Ms. Necheles sang a similar tune to the jury, emphasizing that their clients should not be held accountable for Mr. Weisselberg’s misconduct. New York State law requires that prosecutors prove that Mr. Weisselberg was acting in the company’s interests, not just his own. And that may be the most difficult aspect of the case to prove, given that it’s unclear just how much benefit the company received.

Mr. van der Veen and Ms. Necheles sought to emphasize that section of the law to the jurors and were met several times with objections, which were sustained by Juan Merchan, the judge presiding over the case, who reminded them that explaining the law was his job. Mr. van der Veen then pivoted to arguing that the corporations in fact lost money on Mr. Weisselberg’s schemes.

After opening arguments, the prosecution called its first witness, Jeffrey S. McConney, the Trump Organization’s longtime controller and Mr. Weisselberg’s deputy. During a prosecutor’s questioning of Mr. McConney, jurors began to get a better sense of just how complex the issues at trial will be.

Mr. McConney, who is well over six feet and wears his hair in a silver mullet, at first appeared amiable and willing to respond to questions. When the prosecutor questioned him, Joshua Steinglass, asked that he be considered a hostile witness, jurors appeared confused, and Justice Merchan said no.

It soon became clear why Mr. Steinglass had made the request, which would have allowed him to more directly signal to jurors the purpose of his questions. Without that ability, he and Mr. McConney spent long stretches of time quibbling over fine distinctions in the Trump Organization’s accounting practices.

That portion of the trial made it clear why the prosecution and the defense used their openings to focus, respectively, on Mr. Trump and Mr. Weisselberg. As the evidence began to emerge, it was less about any two individuals than it was tax forms, spreadsheets and numbers. One portion of the afternoon was spent discussing the difference between W2s and 1099s; another, reviewing in detail how to read a general ledger.

The jury responded accordingly.

“Normally, I try to work through the afternoon,” Justice Merchan observed during a break in the questioning. “But I noticed that a couple of the jurors appear to be getting a little tired.”

Lola Fadulu spirit Nate Schweber contributed reporting.

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