• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
Finance

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

Geoff Colvin
By
Geoff Colvin
Geoff Colvin
Senior Editor-at-Large
Down Arrow Button Icon
Geoff Colvin
By
Geoff Colvin
Geoff Colvin
Senior Editor-at-Large
Down Arrow Button Icon
July 3, 2021, 1:00 PM ET

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.

About the Author
Geoff Colvin
By Geoff ColvinSenior Editor-at-Large
LinkedIn iconTwitter icon

Geoff Colvin is a senior editor-at-large at Fortune, covering leadership, globalization, wealth creation, the infotech revolution, and related issues.

See full bioRight Arrow Button Icon

Latest in Finance

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Finance

Markets sell off as U.S.-Iran ceasefire plans go nowhere, leaving Trump with military options to reopen the Strait of Hormuz
EnergyIran
Markets sell off as U.S.-Iran ceasefire plans go nowhere, leaving Trump with military options to reopen the Strait of Hormuz
By Jason MaMay 10, 2026
38 minutes ago
Mah Sing sees natural ‘spillovers’ from Malaysia’s strong growth, as the conglomerate bets on premium residences and data centers
Real EstateSoutheast Asia 500
Mah Sing sees natural ‘spillovers’ from Malaysia’s strong growth, as the conglomerate bets on premium residences and data centers
By Angelica AngMay 10, 2026
2 hours ago
The Strait of Hormuz crisis shows energy security is now a boardroom issue
Commentaryoil and gas
The Strait of Hormuz crisis shows energy security is now a boardroom issue
By Victor NianMay 10, 2026
2 hours ago
Trump quickly blasts Iran’s response to U.S. ceasefire proposal as ‘totally unacceptable’ after warning Tehran ‘will be laughing no longer’
PoliticsIran
Trump quickly blasts Iran’s response to U.S. ceasefire proposal as ‘totally unacceptable’ after warning Tehran ‘will be laughing no longer’
By Jon Gambrell, Samy Magdy and The Associated PressMay 10, 2026
2 hours ago
Market guru Yardeni sees S&P 500 hitting 8,250 this year, highest among top Wall Street forecasters, as earnings bolster ‘Roaring 2020s’
InvestingS&P 500
Market guru Yardeni sees S&P 500 hitting 8,250 this year, highest among top Wall Street forecasters, as earnings bolster ‘Roaring 2020s’
By Jason MaMay 10, 2026
3 hours ago
World’s largest oil company reports 25% profit jump as exports via Saudi Arabia’s East-West Pipeline bypass Strait of Hormuz closure
EnergyOil
World’s largest oil company reports 25% profit jump as exports via Saudi Arabia’s East-West Pipeline bypass Strait of Hormuz closure
By The Associated PressMay 10, 2026
5 hours ago

Most Popular

'Employers are increasingly turning to degree and GPA' in hiring: Recruiters retreat from ‘talent is everywhere,’ double down on top colleges
Future of Work
'Employers are increasingly turning to degree and GPA' in hiring: Recruiters retreat from ‘talent is everywhere,’ double down on top colleges
By Jake AngeloMay 9, 2026
1 day ago
‘This is the way’: Elon Musk endorses Warren Buffett’s famed 5-minute plan to fix the national debt
Economy
‘This is the way’: Elon Musk endorses Warren Buffett’s famed 5-minute plan to fix the national debt
By Jacqueline MunisMay 10, 2026
11 hours ago
OpenAI CEO Sam Altman says Gen Z and millennials are using ChatGPT like a 'life advisor'—but college students might be one step ahead
Tech
OpenAI CEO Sam Altman says Gen Z and millennials are using ChatGPT like a 'life advisor'—but college students might be one step ahead
By Sydney LakeMay 10, 2026
11 hours ago
Ted Cruz says the quiet part out loud: Trump accounts are Social Security personal accounts as GOP senator reveals 'dirty little secret'
Politics
Ted Cruz says the quiet part out loud: Trump accounts are Social Security personal accounts as GOP senator reveals 'dirty little secret'
By Jason MaMay 9, 2026
1 day ago
Red flag test: former CEO explains why he rejects job candidates who say they can start right away
Success
Red flag test: former CEO explains why he rejects job candidates who say they can start right away
By Orianna Rosa RoyleMay 9, 2026
1 day ago
Trump thinks he's flying to Beijing with leverage. China spent 6 years making sure he doesn't have any
Commentary
Trump thinks he's flying to Beijing with leverage. China spent 6 years making sure he doesn't have any
By Steve H. HankeMay 10, 2026
13 hours ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.