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Days before his inauguration in Washington in 2017, Donald J. Trump had a debt to settle in New York: a payout to his fixer, Michael D. Cohen. They met on the 26th floor of Trump Tower, Mr. Cohen says, and struck a $420,000 deal.
Seven years later, Mr. Trump’s criminal trial in Manhattan hinges on that fleeting encounter, which is both critically important and completely in dispute. Mr. Cohen says he paid off a porn star at his boss’s behest, and in that meeting, he and Mr. Trump settled on a plan to repay him and conceal the reimbursement as legal expenses. Mr. Trump says his former fixer is a liar.
But prosecutors say there was a third man in the room that day: Allen H. Weisselberg, Mr. Trump’s moneyman, the keeper of the balance sheet. And he is not saying anything at all.
Prosecutors never called Mr. Weisselberg to testify, because, although he knows the truth, he has not always told it. He is serving time in the Rikers Island jail complex after pleading guilty to perjury in an unrelated civil case involving Mr. Trump, the man he served for nearly half a century.
The defense did not call Mr. Weisselberg either, nor did Mr. Trump take the stand in his own defense. And for weeks, Mr. Weisselberg’s absence has loomed large over Mr. Trump’s case, the first criminal trial of an American president.
In closing arguments on Tuesday, his lawyers are expected to cast Mr. Weisselberg as the prosecution’s missing piece, an elusive central player in the case. They will likely try to argue to the jury that the case depends on Mr. Cohen, whose testimony provided the only evidence that Mr. Trump had direct knowledge of the plot to disguise the hush-money reimbursement as legal fees.
A New York Times examination, based on court records and interviews with a dozen people close to the case, explains Mr. Weisselberg’s absence and reveals a portrait of him as a company man who had a hand in some of Mr. Trump’s shadiest dealings. He could have traded his knowledge for his freedom, but kept his mouth shut, choosing loyalty and lucre — he signed a multimillion-dollar severance deal — over liberty.
For years, the Manhattan district attorney’s office had sought to turn Mr. Weisselberg, 76, against his boss. When he refused, prosecutors indicted him, and by the time the former president’s trial rolled around, they appear to have given up, concluding he would either invoke his Fifth Amendment right to remain silent or outright lie. Ahead of the trial, people with knowledge of the matter said, they did not even bother contacting Mr. Weisselberg’s legal team to see what he might say on the stand.
The Manhattan prosecutors had reason to view him as an unreliable narrator — they are, after all, the same ones who charged him with lying under oath in the civil case.
They also doubted he would tell the truth about the hush-money deal. In the prosecution’s account of that deal, Mr. Trump directed Mr. Cohen to pay the porn star, Stormy Daniels, and then approved Mr. Weisselberg’s plan to fake various documents related to the reimbursement. Those documents account for the 34 felony counts of falsifying business records against Mr. Trump.
But Mr. Trump’s lawyers dispute that the records were false, and for years, the former president has sought to distance himself from the deal.
Mr. Weisselberg has followed his boss’s lead. When federal authorities first examined the deal years ago as part of an investigation into Mr. Cohen, Mr. Weisselberg told a grand jury that he did not recall that Mr. Trump had played a role. The federal prosecutors did not believe him then, the people said, and the Manhattan prosecutors have signaled that they do not believe him now.
So rather than calling him, they sought to enter evidence showing that Mr. Weisselberg was still loyal to Mr. Trump, beholden to the severance agreement that promised to pay him $2 million over nearly two years — if he complied with a key condition: He could not voluntarily cooperate with any investigation.
Mr. Trump’s lawyers objected, arguing that the prosecution should have called Mr. Weisselberg to testify if they wanted to tell the jury about the severance deal. The defense did not call him either, they said, because prosecutors had already used the perjury charge to destroy his credibility.
“The reason Mr. Weisselberg is not a witness to either side is because the district attorney’s office initiated a perjury prosecution in the lead-up to this case,” Emil Bove, one of Mr. Trump’s lawyers, told the judge, Juan M. Merchan, outside the presence of the jury.
Justice Merchan was the only one open to summoning Mr. Weisselberg from jail.
“Has anyone attempted to get him to come in?” the judge asked.
Both sides said they had not. The issue was not raised in open court again.
‘Eyes and Ears’
Mr. Weisselberg got his start with the Trump family as a bookkeeper for Fred Trump, the former president’s father, who was a prominent developer in Brooklyn and Queens. He later took on side projects for Donald Trump and joined him full-time in 1986.
He climbed the ranks of the Trump Organization, where he established an accounting department and ultimately received the title of chief financial officer. In that role, he negotiated financing for the company and helped with Mr. Trump’s tax returns.
He was, he once said, Mr. Trump’s economic “eyes and ears.”
One of Mr. Weisselberg’s sons also joined the Trump Organization, and the two families became fused over the years. Mr. Weisselberg lived in a Trump-branded building in Manhattan. They attended some of each other’s family functions.
And when Mr. Trump was sworn in as president in 2017, he entrusted Mr. Weisselberg, along with Donald Trump Jr. and Eric Trump, with running his company.
Throughout his career, Mr. Weisselberg was woven into Mr. Trump’s homegrown mythology, appearing on his reality television show “The Apprentice” and as a character in some of his many self-help books. In “Trump: Think Like A Billionaire,” Mr. Weisselberg was described as “one of the toughest people in business when it comes to money.”
“He did whatever was necessary to protect the bottom line,” Mr. Trump wrote in the 2005 book, adding, “He’s a loyal employee.”
The Proxy Defendant
In recent years, as two different New York law enforcement agencies investigated Mr. Trump, Mr. Weisselberg paid a steep price for his loyalty.
He took the heat in those investigations, twice landing in jail and once being sued in a case that cost him $1 million.
His run of legal problems began in 2021, when the district attorney’s office charged him and the Trump Organization in a tax fraud scheme. Prosecutors had hoped Mr. Weisselberg might flip and cooperate with their broader investigation into Mr. Trump. That was his only way to remain free.
But when he pleaded guilty in August 2022, he agreed to testify only against the Trump Organization. He would not implicate his boss, and prosecutors insisted he go to jail.
A month after his plea, Mr. Weisselberg and Mr. Trump were sued by the second agency, the New York attorney general’s office, which accused them of orchestrating a conspiracy to inflate the former president’s net worth. The Trump Organization placed Mr. Weisselberg on leave, and ultimately, he left the company — but not without a parting gift.
The day before going to Rikers Island for the first time, Mr. Weisselberg signed the $2 million severance deal, to be paid in installments, with the provision that he not voluntarily cooperate.
Mr. Weisselberg complied with the deal. When the district attorney’s office mounted a final pressure campaign early last year, he once again declined to turn on Mr. Trump.
But his legal troubles were hardly settled. When Mr. Weisselberg emerged from jail, the attorney general’s office summoned him to testify in a deposition in the civil fraud case. And Mr. Trump’s lawyers privately pressed him to testify — both in the deposition and at a trial late last year — hoping the finance chief’s testimony would aid their defense, according to people with knowledge of the discussions.
Mr. Weisselberg’s criminal lawyers expressed concern that testifying could expose him to perjury charges. In the past, he had invoked his Fifth Amendment right not to speak, records show, and his lawyers suggested that he do so again.
But he agreed to testify, and it did not go well. His testimony was not convincing to the judge deciding the case, Arthur F. Engoron, who found him and Mr. Trump liable earlier this year. In his decision, Justice Engoron wrote, “There is overwhelming evidence that Allen Weisselberg intentionally falsified hundreds of business records during his tenure.”
The severance agreement alone, Justice Engoron wrote, “renders his testimony highly unreliable,” adding that, “The Trump Organization keeps Weisselberg on a short leash, and it shows.”
The judge penalized Mr. Weisselberg $1 million and permanently banned him from serving in any New York company in a financial position.
The punishment did not end there. The district attorney’s office determined that Mr. Weisselberg had lied under oath. Mr. Weisselberg pleaded guilty, and last month he was sentenced to another five months in jail.
‘Frick and Frack’
A week later, when prosecutors put Mr. Trump on trial in Manhattan, Mr. Weisselberg did not appear on either side’s witness list.
With Mr. Weisselberg’s credibility already in tatters, the prosecution also appeared to doubt whether he would tell the full truth about the hush-money deal at the center of the case — particularly when it came to Mr. Trump’s reimbursement of Mr. Cohen.
During the federal investigation into Mr. Cohen, who pleaded guilty in 2018 for his role in the hush-money scheme, Mr. Weisselberg had not implicated Mr. Trump in falsifying the reimbursement records. The federal prosecutors, believing he had lied, investigated him for perjury and obstruction of justice, but ultimately did not charge him. And while some of his testimony might have been helpful to prosecutors during Mr. Trump’s current trial, without corroborating Mr. Cohen’s account, it might not have been worth the risk.
Instead, prosecutors introduced a wide variety of evidence that corroborated much of Mr. Cohen’s testimony, but not the crucial description of the January 2017 meeting in Trump Tower.
For years, Mr. Cohen has told a version of that story that has more or less remained the same. In his 2020 book, “Disloyal,” he wrote that Mr. Trump had approved the payment of $420,000 — $130,000 of which he said was reimbursement for the hush money — and seemed to understand ahead of time that the payment would be distributed in 12 payments of $35,000.
“Wow, that’s a lot,” Mr. Cohen recalled Mr. Trump saying.
At the trial, prosecutors elicited a stripped-down version of that account. First, Mr. Cohen explained, he met with Mr. Weisselberg to work out the payment amount. Prosecutors showed jurors notes in Mr. Weisselberg’s handwriting that they said were made during that initial discussion. The notes were written on Mr. Cohen’s bank statement — the very one showing he had paid off Ms. Daniels.
Soon after, Mr. Trump summoned Mr. Cohen and Mr. Weisselberg to his office, where they finalized the plan. Mr. Trump, Mr. Cohen told the jury, “approved” of the arrangement and knew that they would falsify records to cover it up.
To disguise the purpose of the payment to Mr. Cohen, he said, they decided to record it as a legal expense that arose from a “retainer” agreement. There were no such legal expenses, Mr. Cohen testified, nor was there a retainer, but that’s how it appeared on Mr. Cohen’s invoices, Mr. Trump’s ledger and the check stubs used to pay Mr. Cohen.
“Did Mr. Weisselberg say in front of Mr. Trump that those monthly payments would be, you know, like a retainer for legal services?” Susan Hoffinger, one of the prosecutors, asked Mr. Cohen.
“Yes,” he said.
But Mr. Trump’s lead lawyer, Todd Blanche, has argued that Mr. Trump was in fact paying Mr. Cohen for legal services, not reimbursing him for the hush money. He noted that the payment was not for $130,000, but rather for $420,000.
“Ask yourself,” Mr. Blanche, Mr. Trump’s lawyer, said to the jury. “Would a frugal businessman — would a man who pinches pennies — repay $130,000 debt to the tune of $420,000?”
But prosecutors have a simple explanation for the mismatch: Mr. Trump repaid Mr. Cohen for the hush money, and other debts he owed, and Mr. Weisselberg took tax concerns into account.
And Mr. Cohen testified that he had been under the impression that Mr. Weisselberg and Mr. Trump had discussed the extra money before the January 2017 Trump Tower meeting.
“I had been around that office more than enough to realize that this conversation had already taken place between the two,” he said.
Over the course of their decades together, Mr. Cohen knew, Mr. Trump and Mr. Weisselberg had become more or less symbiotic.
“They always played that sort of game of Frick-and-Frack type game,” he said.
Kate Christobek contributed reporting.
