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5 reasons Trump's ex-CFO, testifying in the Trump Org tax-fraud trial, is the worst prosecution witness ever

Nov 18, 2022, 00:27 IST
Business Insider
Donald Trump announcing his 2024 run for president, left, and Trump Organization ex-CFO Allen Weisselberg arriving for his first day of testimony in the company's Manhattan tax-fraud trial, right. Both photos were taken on November 15, 2022.Andrew Harnik/AP, left; Yuki Iwamura/Reuters, right.
  • The Trump Organization tax-fraud trial is in its fourth week; ex-CFO Allen Weisselberg is testifying.
  • Trump's right-hand money man is the prosecution's star witness, but he's also loyal to Trump.
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The Trump Organization was a personal cash machine for its admittedly greedy senior executives — that much is clear from the testimony so far in the company's monthlong criminal tax-fraud trial.

Still, it's Trump's real-estate and golf-resort empire, not his C-suite, that's on trial in a cavernous lower-Manhattan courtroom. To prove the company itself is liable, prosecutors "flipped" Donald Trump's top money man over the summer, and have now hauled him to the witness stand to testify on their behalf.

But was Allen Weisselberg, Trump's first and only chief financial officer, ever really flipped?

And as Weisselberg begins his first full day of testimony Thursday, who will he wind up helping more — the prosecutors he feels unfairly targeted him? Or Trump's company, which is still paying him $1.4 million this year in salary plus bonus?

Here are five reasons Weisselberg is shaping up to be the worst prosecution witness ever.

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1. He's still on Trump's payroll — bigly.

Weisselberg presented himself to the Trump Org's mostly-middle class jury on Tuesday as a very well-paid man.

His salary remains $640,000 a year, he said at the start of his testimony, a tidy sum considering he has been relieved of doing any actual work in light of his August tax-fraud plea.

On top of that salary, Weisselberg collected a $500,000 bonus back in January. Asked by lead prosecutor Susan Hoffinger if he expects another half-million this coming January, he gave something of a sheepish smile.

"I don't know yet," he told her. "Hopefully, yes."

"You expect to be paid a few months after you testify here now?" Hoffinger asked.

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"Correct," Weisselberg answered.

"Who decides if you get the $500,000 dollar bonus?" she asked.

"Eric Trump."

This off-the-bat exchange is interesting on a few levels. One is the obvious: Eric Trump, currently the Trump Organization's top-named executive, will decide whether Weisselberg gets a $500,000 bonus, but will only make that decision after Weisselberg's testimony against the company.

Also interesting: Prosecutors are making it clear to jurors — by practically holding their noses during this bit of direct examination — that their own guy's credibility is in play, a less than ideal circumstance where star witnesses are concerned.

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2. The loyalty goes way back

Weisselberg, 75, has crunched numbers for three generations of Trumps, starting with patriarch Fred Trump in the '70s. He typically worked 10-hour days, according to previous trial testimony. And he was richly rewarded.

Throughout the '80s and beyond, Donald Trump personally signed off on steady raises and bonuses for Weisselberg, his most highly paid executive. When Trump left for Washington in 2017, Eric Trump signed off on more raises and bonuses.

But there was more than just salary and bonuses, as jurors are learning in excruciating, spreadsheet-logged detail.

Jurors have seen Trump's distinctive signature, and that of his eldest son, Donald Trump, Jr., on much of the tax-free perks that are the main evidence at trial. As early as Thursday, they will see more Trump signatures on some $359,000 in checks that paid for five years of private school tuition for Weisselberg's grandchildren.

Another witness on Tuesday, an accounts payable supervisor, characterized that small fortune in tuition checks as a "gift" from Donald Trump to Weisselberg.

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A still larger "gift" from the boss came in 2005, after Weisselberg's wife, Hilary, underwent a series of eye operations and needed to spend the winter months in Florida to save her eyesight.

Trump personally suggested that Weisselberg stop making the three-hour round-trip commute to and from an empty house in Long Island each day and move instead into a Trump-branded apartment with a terrace overlooking the Hudson River, Weisselberg told jurors.

The apartment, at 140 Riverside Boulevard, along with its utilities and garage fees — a package worth some $200,000 a year — would be the most valuable perk in the tax-dodge scheme that prosecutors are trying to pin on the company.

The defense can't distance itself from that apartment. Trump's signature is all over the paperwork. But on the stand, Weisselberg spun it as not a tax-dodge at all, but a gesture of largess and compassion.

"Donald knew that while she was there," in Florida, "I was going home every night to an empty house," on Long Island, Weisselberg testified, his voice forlorn. "There was nobody there."

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The prosecution has yet to prove that this "kindly boss" defense, describing a loyalty-generosity feedback loop going back decades, is a convenient cover story for a calculated partnership in fraud.

3. He won't hurt anyone named Trump

Weisselberg has made clear since his guilty plea that he'll testify about his own tax-dodging, but he won't incriminate anyone named Trump, not Donald Trump or any of his three oldest children, all of whom have served as company vice presidents.

"Did you conspire with any member of the Trump family?" defense lawyer Alan Futerfas asked as cross-examination began Thursday.

"No," Weisselberg answered.

"Did you scheme with any member of the Trump family?" the lawyer asked.

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"No," he answered.

Prosecutors have tried to pressure Weisselberg, defense lawyers have complained in pre-trial filings, by telling him that if he did not come up with the goods on the former president, he could face a year or more in prison.

But throughout last summer, Weisselberg wouldn't budge, instead insisting Trump had done nothing wrong, the filings said.

Ultimately, none of Trump's C-suite would cooperate against Trump personally in a pair of three-year probes by the Manhattan district attorney's office and the state attorney general's office, as Insider reported earlier this year.

4. He may not need to hurt Trump to keep his deal

Doesn't Weisselberg have to implicate the company to keep his plea deal, which with good behavior would let him serve just 100 days in jail instead of a potential 15 years in state prison?

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Not necessarily.

Before they begin deliberations sometime next month, jurors will be told by state Supreme Court Justice Juan Merchan that prosecutors must prove that company executives — Weisselberg and controller Jeffrey McConney, who has testified in the trial under a grant of immunity — did not cheat on their taxes for 15 years merely for their own benefit.

They had to have intended to help the company, too, in order for the company to also be liable.

Nowhere in Weisselberg's plea allocution, though it was written by prosecutors, does he admit any intent to help the company.

It's hard to imagine him admitting to it now, for the first time, on the witness stand.

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5. He's coordinating his testimony with the defense

Instead, jurors are likely to continue to hear, and this time from his own mouth, what has has become something of a mantra for the defense: "Weisselberg did it for Weisselberg."

"Donald Trump didn't know that Allen Weisselberg was cheating on Allen Weisselberg's personal tax returns," one defense lawyer, Susan Necheles, told jurors during opening statements.

"The meat of our defense," another defense lawyer, Michael van der Veen told jurors in his own openings, "is that Allen Weisselberg did not act at all with the intent to benefit" the company.

What's more, he said, Weisselberg hid from the Trump family the fact that he was failing to pay income taxes on hundreds of thousands of dollars a year in free cars, tuition payments, and the use of a rent-free apartment.

Weisselberg likely got the "Weisselberg did it for Weisselberg" defense memo — he's been meeting with defense lawyers as well as with prosecutors in preparing his testimony, and his own defense bills are being paid by Trump.

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The prosecution, meanwhile, is fighting hard against the defense theories that Weisselberg didn't intend to benefit his bosses and kept them in the dark.

Donald Trump or Eric Trump approved those executive salaries, bonuses and perks, Hoffinger, the prosecutor, told jurors, who have seen many of the signed checks and signatures that prove this.

And when Weisselberg or any other executive took chunks of their salaries in the form of tax-free perks, the company saved on payroll taxes and Medicaid withholding, prosecutors argued — relatively small sums, but still a benefit to the company.

The problem for prosecutors will be meeting the legal requirement of proving that Weisselberg intended to bestow these small benefits on his company. For all of the reasons above, that's a problem Weisselberg appears unlikely to help them with.

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