Former president Donald Trump is pictured with his former CFO Allen Weisselberg
President Donald Trump with his then CFO Allen Weisselberg at Trump Tower in 2017.Evan Vucci/AP
  • Allen Weisselberg, the CFO of the Trump Organization, is going to jail for tax fraud.

  • He could face more time than the five months he was sentenced for.

  • Weisselberg could be found guilty of violating the deal because jurors found him guilty of lying.

If a judge finds that the executiveshaded the truth on the witness stand, he could face more time in prison.

An updated sentencing date has been set for Allen Weisselberg, the company's former CFO.

He will be sentenced to five months in jail as part of his plea deal.

Weisselberg had to testify against Trump's real-estate company in order to get the deal done. The verdict itself has thrown into doubt whether he did so.

Insider talked about Weisselberg's testimony and plea deal with five former white-collar-crime prosecutors from the Manhattan district attorney's office.

The jury didn't believe the ex-CFO when he denied on the witness stand that he also intended to benefit Trump's company, according to all of them. Under New York's corporate-liability law, intent to benefit the company is important.

The jury's no-confidence vote and the prosecution's distrust of Weisselberg would allow the trial judge to hike the sentence.

Diana Florence, who handled complex enterprise-corruption cases as chief of the construction-fraud task force, said that he didn't tell the truth and the deal is off the table.

"Weisselberg said over and over, 'I, together with the Trump Organization,'" said Florence, now in private practice. He got on the stand and said he was the one who did it.

Adam Kaufmann, a former investigations chief at the office, said that he kept to his story that it was all about him.

Kaufmann is a partner at Lewis Baach Kaufmann Middlemiss, PLLC. They didn't think he was right.

Prosecutors, too, implied their own witness lied

New York's corporate-liability law made it difficult for the Trump Organization trial prosecutors to question Weisselberg's testimony.

It's not enough for executives to break the law for their own benefit in order for a company to be held liable. Weisselberg denied that the executive intended to benefit the company more than a dozen times.

Weisselberg had at least some intent to benefit the corporations according to the evidence presented by the prosecution.

Steinglass didn't call Weisselberg a liar. He warned jurors that Weisselberg's narrative was a lie.

Steinglass accused the former president of "sanctioning tax fraud" in his closing argument.

Assistant District Attorney Joshua Steinglass.John Minchillo/AP

The trial's two lead prosecutors, Steinglass and Hoffinger, presented evidence that the former president personally signed hundreds of invoices, memos and bonus checks, saving millions of dollars.

Steinglass suggested that Weisselberg was coached and paid to protect Trump's company.

Steinglass told the jury that Weisselberg has a half a million reasons to shade the truth towards their side of the room.

After he agreed to testify against them, why did they not fire him? Steinglass asked the jury a question.

The prosecutor said that Allen wouldn't get that half-a-mil if he said too much. He said that his plea deal required him to pay back $2 million in taxes, interest, and penalties.

Weisselberg is still on paid leave. Michael Cohen told Insider of Weisselberg that he didn't think he'd be fired.

Cohen said that they needed him to stay quiet.

Will the DA hold Weisselberg to account?

The Manhattan District Attorney can call Weisselberg to account for "shading the truth" according to his own prosecutor.

Weisselberg's lawyer says the additional time Bragg can recommend is 100 days with good behavior.

Steinglass told the judge that if Weisselberg didn't live up to the conditions of his plea, the people would recommend a large state prison sentence.

The district attorney's recommendation to the judge will not be made public.

The office noted that the majority of Weisselberg's testimony was crucial to the conviction.

Nicholas Gravante Jr., Weisselberg's lawyer, is expected to make a strong argument that his client lied to the jury. The jurors didn't think he was right.

Weisselberg, center, and his attorney Nicholas Gravante Jr., right, at the courthouse for the Trump Organization's Manhattan tax-fraud trial, on November 15, 2022.Seth Wenig/AP

Weisselberg testified that Trump was not involved in the tax-dodge scheme.

The legal situation of Mr. Weisselberg is unaffected by the jury's verdict, according to Gravante.

The only obligation he had was to tell the truth in the trial.

The judge gets the final say

Weisselberg's lawyer doesn't have final say on his sentence.

John Moscow was a complex economic crimes prosecutor for the district attorney's office for 30 years.

A judge could say "You entered into an agreement before me that you testify honestly" Moscow said the jury found you lied.

Judge Juan Merchan in courtroom-artist sketch.REUTERS/Jane Rosenberg

The ex-prosecutors had differing opinions on what would happen next.

One requesting anonymity said that he wouldn't be surprised if the judge gave him more time.

When it came to the intent to benefit the company part of Weisselberg's testimony, it was clear that jurors didn't believe him.

The judge may be reluctant to "rock the boat" if Bragg doesn't request additional time.

He said that it would be unlikely that the judge would slam Weisselberg because of the original plea deal. Lawyers for the Trump Organization plan to appeal the verdict.

The judge doesn't want to see any more of the litigation. I'm sure he was interested in it. It wasn't a big deal.

Business Insider has an article on it.