Allen Weisselberg could get more time since the Trump Org guilty verdict required jurors to find he lied

• Only one person, ex-CFO Allen Weisselberg, is going to jail for the Trump Org. tax-fraud scheme.
• Ex-Manhattan financial-crimes prosecutors say he could now face more time than his five-month deal.
• A judge could rule Weisselberg violated the deal because jurors, by their verdict, found he lied.

The lone executive going to jail in the aftermath of last week's Trump Organization tax-fraud conviction could face more time behind bars if a judge finds — as a prosecutor suggested to jurors in closing arguments — that he "shaded the truth" on the witness stand.

Allen Weisselberg, the company's former chief financial officer, will learn his fate in a Manhattan courtroom on January 10, his updated sentencing date.

He has been promised a five-month jail sentence as part of his August plea deal.

But that deal required Weisselberg, 75, to testify truthfully against former President Donald Trump's real-estate company, where he's worked since the 1970s. Whether he did so has been thrown into doubt by prosecutors and the verdict itself.

Insider talked about Weisselberg's testimony and plea deal with five former white-collar-crime prosecutors from the Manhattan district attorney's office, and with Cy Vance, the former district attorney who brought the original Trump Organization case before leaving office.

All of them said that by finding Weisselberg guilty, the jury showed it did not believe the ex-CFO when he repeatedly denied on the witness stand that in running a 13-year tax-dodge scheme for himself and fellow executives he also intended to benefit Trump's company. Intent to benefit the company is vital for a conviction under New York's corporate-liability law.

This no-confidence vote from the jury, especially when coupled with the prosecution's open-court distrust of Weisselberg, their own star witness, would allow the trial judge, New York Supreme Court Justice Juan Merchan, to revoke the plea deal and hike the sentence, the ex-prosecutors said.

"I would argue that he didn't tell the truth and the deal is off the table," said Diana Florence, who handled complex enterprise-corruption cases as chief of the construction-fraud task force during her 25 years as a Manhattan prosecutor.

"Weisselberg says over and over, 'I, together with the Trump Organization,'" Florence, now in private practice, noted of his guilty plea. "Then he gets on the stand and says, 'It was just me.'"  

"He kept to his story that it was all about me and Trump didn't know anything," said Adam Kaufmann, a former investigations chief at the office.

"It was a nice try," added Kaufmann, now a partner at Lewis Baach Kaufmann Middlemiss, PLLC. "But they didn't believe him."

Prosecutors, too, implied their own witness lied

Weisselberg's truthfulness was also repeatedly challenged by Trump Organization trial prosecutors, who were forced by the language of New York's corporate-liability law to cast doubt on their own star witness.

The law says that for companies to be liable for their executives' crimes, it's not enough that those executives broke the law for their personal benefit. The executive must also intend to benefit the company, something Weisselberg denied more than a dozen times throughout three days of testimony.

"The evidence is crystal clear that he had at least some intent to benefit the corporations," prosecutor Joshua Steinglass told jurors in closing arguments, directly refuting Weisselberg on that key legal element.

Steinglass stopped just short of calling Weisselberg a liar to the jury. Instead, he called Weisselberg's "betrayal narrative" a lie, warning jurors it was "completely false."  

"Donald Trump knew exactly what was going on with his top executives," Steinglass said in his closing arguments, at one point accusing the former president of "sanctioning tax fraud."

Steinglass and Susan Hoffinger, the trial's two lead prosecutors, spent the trial presenting ample, convincing evidence that the former president saved millions through the scheme and personally signed hundreds of its underlying invoices, memos, and bonus checks.

Steinglass even went so far as to suggest that Weisselberg — who admittedly prepped with Trump Organization lawyers, conferring with them even during breaks in his testimony — was coached and paid to protect Trump's company.

"He has a half a million reasons to kind of shade the truth towards their side of the room," Steinglass told the jury, a reference to a possible $500,000 annual bonus Weisselberg is hoping for in January, on top of his $1.14 Trump Organization pay package for 2022.

"Why do you think they didn't fire him after he agreed to testify against them?" Steinglass asked the jury, his voice turning sarcastic.

"Don't say too much, Allen, or you won't get that half-a-mil," the prosecutor said mockingly. "We know you need it to pay back the $2 million you owe the state" in taxes, interest, and penalties, as mandated in his plea deal, he added.

Weisselberg remains on paid leave as a Trump Organization special advisor. "I don't think he'll get fired," Trump whistleblower Michael Cohen told Insider of Weisselberg, whom he'd worked with closely as the company's former top lawyer.

"They still need him to stay quiet," Cohen said.

Will the DA hold Weisselberg to account?

Manhattan District Attorney Alvin Bragg has the authority to continue to call Weisselberg to account for "shading the truth," as his own prosecutor put it.

At next month's sentencing, Bragg can recommend additional time beyond the promised five months, which Weisselberg's lawyer says amounts to 100 days with good behavior.

Steinglass had threatened to do as much during Weisselberg's plea hearing, telling the judge, "If the defendant does not live up to the conditions of the plea, including giving truthful testimony at trial, then the People will recommend significant state prison." 

A spokeswoman wouldn't say what the district attorney's recommendation to the judge will be at next month's sentencing.

But the office has noted that the bulk of Weisselberg's testimony, in which he described the intricate workings of the tax-dodge scheme itself, was crucial to winning last week's 17-count conviction.

Weisselberg's lawyer, Nicholas Gravante Jr., is meanwhile expected to make a strong argument at sentencing that his client indeed testified truthfully. Jurors just didn't believe him.

Weisselberg has long insisted that Trump was not complicit in the tax-dodge scheme, and his testimony never diverged from that, Gravante said. 

"The verdict reached by the jury has no effect on Mr. Weisselberg's legal situation," Gravante, a partner at Cadwalader, Wickersham & Taft, LLC, told Insider.

"His only obligation relating to the trial was that he testify truthfully, and clearly he did." 

The judge gets the final say

Ultimately, neither prosecutors nor Weisselberg's lawyer gets the final say at his sentencing.

"There's another party in there," said John Moscow, who prosecuted complex economic crimes for the district attorney's office for 30 years.

"A judge could say, 'You entered into an agreement before me that you testify truthfully. By their verdict, the jury found you lied,'" said Moscow, now senior counsel at Lewis Baach Kaufmann Middlemiss.

Ex-prosecutors offered a range of opinions on what will happen next. 

"I wouldn't be surprised if the judge gives him more time," said one, requesting anonymity because of a continuing connection to the district attorney's office.

Cy Vance, the former Manhattan district attorney who brought the Trump Organization tax-fraud case before leaving office, said it was "absolutely" clear that jurors didn't believe Weisselberg, not when it came to that vital "intent to benefit the company" portion of his testimony.

But Vance thought Merchan, the judge, may be reluctant to "rock the boat," especially if his successor, Bragg, does not ask for additional time.

"I think it would be unlikely that this judge would slam Weisselberg," he said, noting, as did other former prosecutors, that any deviation from the original plea deal will mire the case in yet another appeal. Trump Organization lawyers have already promised to appeal the verdict itself.

"I think this is the last he wants to see of the Trump litigation," Vance added of the judge. "I'm sure he thought it was an interesting case. But it was a headache."