Trump’s Master Plan to Win His Company’s Criminal Trial: Blame His Own Money Man

Former President Donald Trump’s company rolled out its master plan to win an acquittal in its criminal trial on Monday: Blame Trump’s longtime top money man, Allen Weisselberg—and, while blasting him as a self-dealing, untrustworthy criminal, continue paying him part of his once-lavish $1 million annual salary. 

Lawyers for the Trump Organization came out swinging in the trial’s opening arguments Monday against the elderly financier who loyally served Trump’s family business for some five decades, rose to become its chief financial officer, and then admitted to tax crimes in August and agreed to testify against the company in its criminal tax fraud case.

Yet the Trump Organization’s bizarre and seemingly contradictory position on Weisselberg—that he’s a greedy felon who also deserves to keep drawing a company paycheck—underscores the key question about the prosecution’s supposed star witness in this trial: Whose side is Trump’s money man really on? 

Weisselberg refused to cooperate in the broader investigations into Trump individually but now faces deadly-serious criminal jeopardy if he fails to assist the prosecutors battling Trump’s company in this trial. The judge warned Weisselberg that he could add more than a decade to Weisselberg’s five-month sentence if the financier lies to protect Trump on the stand. Weisselberg won’t be sentenced until after the trial ends. 

This dynamic puts Weisselberg in a dangerous situation with mixed incentives: a financial incentive that aligns with Trump’s company, but also a legal imperative to help prosecutors nail that same company for alleged crimes. The forthcoming trial may now turn on how Weisselberg navigates that situation when he testifies in the coming weeks.

Weisselberg, 75, pleaded guilty to 15 felonies in August after prosecutors accused him and Trump’s company of channeling off-the-books benefits to senior executives to avoid taxes. For Weisselberg, those payments covered his luxury apartment, multiple Mercedes Benzes, a New York City parking space, and private school tuition for his grandchildren. Two Trump Organization entities—the Trump Corporation and Trump Payroll Corp.—are now on criminal trial for their part in the same scheme.

Prosecutor Susan Hoffinger promised Weisselberg will reveal the “inside story” of what really went down inside Trump’s company.

“This case is about greed and cheating—cheating on taxes,” Hoffinger told the jury on Monday. “The Trump Corporation and the Trump Payroll Corporation paid their already highly-paid executives even more by helping them cheat on taxes.”

Lawyers for the companies likewise came out blasting Trump’s former CFO for the one thing that everyone in the courtroom seemed to be able to agree about: Weisselberg’s greed. 

“Allen Weisselberg is a man who has fallen to his greed!,” Trump corporate lawyer Michael Van Der Veen thundered to the jury. “Greed made him cheat on his taxes, hide his deeds from his employer, and betray a trust built over nearly 50 years!”

But Trump’s lawyers also told the jury that Weisselberg’s claims could not be trusted.

Weisselberg would tell the jury things that “simply make no sense,” said Susan Necheles, a lawyer for the Trump Corporation. 

Weisselberg had lived a life of luxury while working for Trump, and only agreed to cooperate under threat of a lengthy prison sentence, she said. 

“Once he was arrested, he realized he was in danger of losing all of it and being sentenced to jail for years,” Necheles said. “So Allen Weisselberg made a deal with the prosecutors.”  

Lawyers for Trump’s company argued Monday that Weisselberg committed tax crimes for his own benefit, rather than for the benefit of the company. 

Weisselberg has been put on a leave of absence from his position as Chief Financial Officer and is now receiving less from the company than his previous $1 million-per-year income, Van Der Veen told the jury. The company decided to keep paying him in order to let him support his family, he said. 

“He still gets some pay,” Van Der Veen admitted, after denouncing Weisselberg as a greedy criminal.

Weisselberg isn’t the only witness for the prosecution still drawing a paycheck from Trump’s family business. 

The prosecution’s first witness was Weisselberg’s longtime deputy Jeff McConney, Trump Org senior vice president and controller. McConney admitted under oath on Monday that he earned roughly $450,000 from the company last year, and that the company is also paying his lawyer bills in this trial.

In a contentious moment of the trial, prosecutor Joshua Steinglass attempted to designate McConney a hostile witness, in a move that would have allowed the prosecution to ask him leading questions. Judge Juan Merchan denied the request on the grounds that McConney hadn’t refused to answer any questions yet. 

The criminal fate of Trump’s company likely now rests on what the jury makes of these Trumpworld insiders. Weisselberg’s fate, meanwhile, may now lie in whether lawyers for Trump’s company can persuade the jury not to believe ] Weisselberg, without also convincing the judge to tear up his plea deal for lying. 

Weisselberg agreed to testify at this trial in exchange for a much-reduced sentence of five months, versus the 15 years he might have received if he had refused to testify and gone to trial. 

Weisselberg’s refusal to fully cooperate with prosecutors from the Manhattan District Attorney’s office is one reason why Trump himself was not personally charged in this case. 

Yet the names of Trump family members were bandied about the courtroom rapidly during opening arguments and the questioning of McConney—raising clues about how the trial may reveal details of how Trump ran his company and what he and his family members knew about the firm’s alleged crimes. 

Hoffinger, the prosecutor, told the jury that Trump personally signed the tuition checks for Weisselberg’s grandchildren’s private school, but later stopped signing them after he won the presidency due to concerns about the enhanced scrutiny that he and his business would face. 

Trump has not been accused of any crimes, and neither has any of his adult children (Don Jr., Eric, or Ivanka). The former president has blasted the case as part of an unfounded witch hunt led by his Democratic enemies. The charges against Weisselberg and Trump’s company were brought by Manhattan District Attorney Alvin Bragg, an elected Democrat. 

Trump corporate defense attorney Necheles insisted to the jury that Trump had no knowledge that Weisselberg had criminally reduced the size of his personal income checks in ways that also cut his payroll taxes. 

“Donald Trump didn’t know that Allen Weisselberg was cheating on Allen Weisselberg’s personal tax returns,” Necheles told the jury. “The evidence will be crystal clear on that.” 

Weisselberg agreed to spend five months in New York’s notorious Rikers Island jail complex in exchange for his guilty plea. If that deal holds, and with good behavior, he may spend only 100 days behind bars.