Members Only | August 22, 2022 | Reading Time: 3 minutes

Allen Weisselberg can’t plead the Fifth anymore

He used to protect Donald Trump that way. But no more.


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Donald Trump’s top financial officer Allen Weisselberg pleaded guilty Thursday to 15 felonies, including tax fraud. The Trump Organization itself stands charged with similar crimes. Legally, Weisselberg’s guilt is tantamount to the Trump Organization’s. 

The former president is not charged in this case, but the indictment alleges that he participated in at least one aspect of the scheme. 

Weisselberg could reveal very damaging information about the inner workings of Trump’s business and his personal misconduct without technically cooperating with the criminal probe against his boss.

The Trump Organization is the nerve center of Trump’s empire. It’s accountable only to him. If the organization is found guilty, the company could face large fines or roadblocks to future deals. 

That would hit Trump’s pocketbook directly. But more importantly Weisselberg could potentially testify that Trump personally, knowingly and willfully participated in the tax scam. 

A primitive scheme
Weisselberg was facing 15 years maximum, but he agreed to plead guilty in exchange for a five-month sentence, of which he’ll probably only serve 100 days at Rikers Island. He agreed to testify against the Trump Organization, but he didn’t agree to cooperate with the larger criminal investigation into Donald Trump personally. This is face-saving for Weisselberg who can say that he stayed loyal to his boss of 50 years, but this may be a distinction without a difference. 

Weisselberg pleaded guilty to administering and benefiting from a primitive tax-avoidance scheme. Some senior Trump Organization managers were paid in lavish fringe benefits such as rent-free apartments, leased luxury cars and private-school tuition payments. 

As a result, their paychecks were smaller. They paid fewer taxes. The Trump Organization dodged taxes on their artificially small payroll. 

Weisselberg failed to report nearly $1.8 million in income over 15 years that included the value of a rent-free apartment on Riverside Boulevard in Manhattan, leased Mercedes-Benzes for himself and his wife and private school tuition for his grandkids. 

The indictment alleges that some of the tuition was paid by checks drawn on Trump’s personal account, signed by Trump personally. 

If the Trump Organization insists on taking this case to trial, Weisselberg could theoretically testify that Trump knew he was writing those checks as part of the scheme. 

Still a black box
The criminal investigation of Trump reportedly stalled out because New York District Attorney Alvin Bragg worried that he couldn’t prove that Trump knowingly falsified the value of his assets. The prosecutors who investigated Trump insisted they could prove multiple felonies, but Bragg’s the man in charge.

After so many years and so many investigations, the Trump Organization is still a black box. Trump’s top lieutenants have for years thwarted investigations by pleading the Fifth. 

The challenge in white collar cases is proving that the boss knowingly and willfully participated and that the crimes weren’t just the work of overzealous underlings. Trump’s lieutenants routinely refuse to answer basic questions under oath about how the company is run and who makes decisions, on the grounds that it might incriminate them. 

For years, Weisselberg invoked his right against self-incrimination whenever investigators questioned him about Trump’s business dealings, even the most basic aspects of how the business operated. 

But now Weisselberg can’t take the Fifth about any of the crimes he’s already pleaded guilty to. He already incriminated himself on those. 

De facto life sentence
More to the point, since his sentencing isn’t until after the Trump Organization’s trial, he’s testifying with a 15-year prison term hanging over his head, a de facto life sentence for a frail 75-year-old man.

That’s a big incentive not to get cute with prosecutors who ask uncomfortable questions. That kind of testimony could be useful to investigators and possibly even to future prosecutors. 

Weisselberg could reveal very damaging information about the inner workings of Trump’s business and his personal misconduct without technically cooperating with the criminal probe against his boss. 

Lindsay Beyerstein covers legal affairs, health care and politics for the Editorial Board. An award-winning documentary filmmaker, she’s a judge for the Sidney Hillman Foundation. Find her @beyerstein.

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