CryptocurrencyInvestingBanksReal Estate

The striking parallels between the allegations in the Trump Organization indictment and routine practices at Bernie Madoff’s firm

July 3, 2021, 5:00 PM UTC

The allegations in the recent indictment of the Trump Organization and CFO Allen Weisselberg seem like penny-ante charges. They’re not. For Trump and his colleagues, they’re more ominous than they appear.

The indictment by Manhattan District Attorney Cyrus R. Vance Jr. accuses Weisselberg and the Trump Organization of defrauding federal, New York State, and New York City tax authorities. In a world of multi-billion-dollar scams, the numbers are not mind-boggling. Weisselberg is accused of evading $901,112 of taxes over a 15-year period.

His lawyers insist the indictment is purely politically motivated. “It is now open season for local prosecutors to target federal political opponents,” they said. In a statement, the Trump Organization says this is a case “that neither the IRS nor any other district attorney would ever think of bringing.” Former Trump adviser Jason Miller ridiculed the case for accusing Weisselberg of “maybe taking free parking” since it includes a charge that the Trump Organization paid his garage expenses without reporting the payments as employee compensation, and Weisselberg didn’t report them as pay.

After almost three years of investigation, this is what they’ve got?

But these allegations could mean much more. To see why, consider how strikingly they resemble what went on for years at Bernard L. Madoff Investment Securities.

The central accusation in the indictment is that the Trump Organization directly paid certain expenses of Weisselberg and other senior executives rather than putting that money in their paychecks, without anyone reporting those payments to the IRS as employee compensation. The same practice was routine at the Madoff firm. For example, the Trump Organization for years directly paid the rent on Weisselberg’s New York City apartment, plus electricity, telephone, cable, Internet, and parking, says the indictment. At the Madoff firm, the company directly paid the maintenance costs of three New York City apartments for CFO Daniel Bonventre.

The Trump Organization paid the tuition for two of Weisselberg’s family members at a private school in Manhattan, says the indictment. The Madoff firm paid the tuition of Bonventre’s sons at a private school in Manhattan. The Trump Organization paid many Weisselberg personal expenses at his request, the indictment alleges: new beds, flat-screen TVs, carpeting and furniture for his Florida home, for example. The Madoff firm paid many of Bonventre’s personal expenses at his discretion: country club dues, season tickets to the New Jersey Devils hockey team, for example.

The obvious question is why? These men were making a lot of money, and those expenses weren’t crushing. Why go through such financial contortions? Answer: It wasn’t about the money.

“What allegedly happened here and happened in the Madoff case is a white-collar equivalent of what goes on in a Mafia gangster case,” says Roland Riopelle, a defense attorney and former federal prosecutor in the Southern District of New York who represented a Madoff employee, Annette Bongiorno, in that scandal’s aftermath. “Members of the conspiracy are encouraged to commit crimes, using the organization for their own benefit. That ultimately becomes the way in which the organization binds the individual to it and encourages loyalty.”

It’s what Riopelle calls “false generosity as a way of keeping people in place. It’s false generosity because with each gift, the recipient is sinking deeper into criminality.”

Riopelle doesn’t believe the indictment is insignificant. On the contrary, he says, it’s “just the first move on the chessboard” and “a smart strategic move.” That’s not only because it’s a clear attempt to “flip” Weisselberg. It will also “disrupt the legitimate banking relationships of the company, cripple it, and probably have a crippling effect on Mr. Trump’s ability to defend himself.” He says he was surprised that the indictment didn’t include a charge under New York State’s equivalent of the federal RICO (Racketeer Influenced and Corrupt Organizations) law. “That may have been held back as a threat,” he says. “I expect we’ll see that charge levied against the Trump Organization at some point. It carries a heavier criminal penalty in terms of imprisonment for an individual, and it’ll be much more difficult to defend against.”

As for the Trump Organization’s claim that other prosecutors wouldn’t have brought this case, Riopelle says, “That really is not true.” What’s alleged in the indictment is “a fairly common type of tax evasion. It is often prosecuted.” A notable example, he observes, was Trump’s former lawyer and longtime mentor, Roy Cohn, who in 1986 was “indicted for exactly this conduct” by then-U.S. Attorney Rudolph Giuliani. Cohn went to trial and was acquitted. Weisselberg and the Trump Organization may likewise prevail in this legal battle. But the parallels are not reassuring.

Subscribe to Fortune Daily to get essential business stories straight to your inbox each morning.