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

Trendingnow

1

U.S. Treasury has borrowed $155 billion every month of this fiscal year—and is now paying $24 billion a week in interest on its debts

2

Top Iranian officials admitted to the supreme leader that the U.S. naval blockade was crushing the economy, report says, as Trump eyes reimposing it

3

Billionaire MacKenzie Scott just donated $20 million to support America’s youth mental health, as a fifth of teens struggle with suicidal thoughts

1

U.S. Treasury has borrowed $155 billion every month of this fiscal year—and is now paying $24 billion a week in interest on its debts

2

Top Iranian officials admitted to the supreme leader that the U.S. naval blockade was crushing the economy, report says, as Trump eyes reimposing it

3

Billionaire MacKenzie Scott just donated $20 million to support America’s youth mental health, as a fifth of teens struggle with suicidal thoughts
PoliticsCrime

Donald Trump’s longtime CFO chokes up over betraying the family’s trust as he testifies his tax fraud didn’t involve them

By
Michael R. Sisak
Michael R. Sisak
and
The Associated Press
The Associated Press
Down Arrow Button Icon
By
Michael R. Sisak
Michael R. Sisak
and
The Associated Press
The Associated Press
Down Arrow Button Icon
November 17, 2022, 3:45 PM ET
Allen Weisselberg
Trump Organization's former Chief Financial Officer Allen Weisselberg arrives to the courtroom in New York, Thursday, Nov. 17, 2022.AP Photo/Yuki Iwamura
Add Fortune on Google for similar content.

Donald Trump’s longtime finance chief choked up on the witness stand Thursday, saying he betrayed the Trump family’s trust by scheming to dodge taxes on $1.7 million in company-paid perks, including a Manhattan apartment and luxury cars.

Allen Weisselberg, a senior adviser and ex-chief financial officer at the former president’s Trump Organization, said he conspired with a subordinate to hide more than a decade’s worth of extras from his taxable income, but that neither Trump nor his family were involved in the scheme.

The Trump Organization is now on trial, accused of helping Weisselberg and other executives avoid paying income taxes on compensation in addition to their salaries. Prosecutors argue the company is liable because Weisselberg was a “high managerial agent” entrusted to act on its behalf.

“It was my own personal greed that led to this case,” said Weisselberg, who pleaded guilty to tax crimes and agreed to testify against the company in exchange for a five-month jail sentence.

Asked if he was embarrassed by what he did, a somber Weisselberg said: “More than you can imagine.”

His emotional testimony came on his second day as the prosecution’s star witness, as a company lawyer reminded him on cross-examination of the faith that the Trump family had put in him for decades.

Weisselberg started working for Trump’s father in 1973 and joined Trump as an executive at his then-fledging Trump Organization in 1986. He wielded immense power as the company, buoyed by Trump’s celebrity, grew from a modest New York City developer into a global golf, hotel and real estate empire.

Weisselberg also recalled helping Trump through the company’s dark times in the early 1990s — including casino bankruptcies and the failure of his Trump Shuttle airline. He reminisced about watching Trump’s three eldest children — Donald Jr., Ivanka and Eric — grow up before his eyes, admitting he was “among the most trusted people they knew.”

The Trump Organization denies wrongdoing. The company could be fined more than $1 million if convicted, but a guilty verdict could also hamper the company’s ability to get loans and make deals and lead to attempts by governments, such as New York City, to cancel contracts with Trump entities.

The Trump Organization continues to employ Weisselberg, paying his usual $640,000 salary even after he went on leave of absence last month. In court, though, the company’s lawyers have portrayed Weisselberg as a loyal lieutenant who went rogue and concocted the tax dodge scheme on his own without Trump or the Trump family knowledge.

Some of Weisselberg’s testimony appeared to underscore that point. But, the 75-year-old executive refuted the defense’s contention that his scheme didn’t help company’s bottom line, too. He also detailed another financial arrangement, involving holiday bonuses, that had saved the company money for years.

Weisselberg testified that he conspired to hide his perks with the company’s senior vice president and controller, Jeffrey McConney — doing so by fudging payroll records to deduct their cost from his salary. The arrangement reduced Weisselberg’s tax liability, while also saving the company money because it didn’t have to give him a hefty raise needed to cover the cost of the perks and additional income taxes he’d incur.

The company’s chief operating officer, Matthew Calamari Sr., also reduced his salary to deduct the cost of a company-paid apartment and cars for him and his wife, but Weisselberg denied they were in cahoots. He said he had no knowledge of or involvement in what Calamari was doing.

Calamari has not been charged with a crime. McConney, who was granted immunity, testified for the first five days of the trial in state court in Manhattan.

Weisselberg told jurors that Trump signed off on his apartment lease and, until becoming president in 2017, personally paid private school tuition for his two grandchildren.

The company, however, did have a longstanding practice to avoid taxes on the lucrative Christmas bonuses that Trump handed out each year to his company’s executives.

Weisselberg said the company ducked taxes for decades by drawing some bonus checks signed by Trump from subsidiary entities and paying executives as independent contractors, allowing the company to avoid payroll taxes and the subsidiaries to deduct the bonuses as expenses.

Weisselberg said the practice began before he started at the Trump Organization and was only abandoned after a tax lawyer audited the company’s pay practices once Trump became president in 2017.

Trump “always wanted to sign the bonus checks,” Weisselberg said — applying his distinct, seismograph-like signature to a stack of 70 or more checks made out to key company officials, including Weisselberg and Calamari.

The checks would then be stuffed into Christmas cards, also signed by Trump, who then acted like Santa Claus, handing them out to executives around the company’s Trump Tower offices.

The Trump Organization switched to paying executive bonuses entirely as taxable employee income once Trump went to the White House.

“We were going through an entire cleanup process at the company. With Mr. Trump now president, we wanted to make sure everything was done properly,” Weisselberg said.

Our new weekly Impact Report newsletter will examine how ESG news and trends are shaping the roles and responsibilities of today's executives—and how they can best navigate those challenges. Subscribe here.

About the Authors
By Michael R. Sisak
See full bioRight Arrow Button Icon
By The Associated Press
See full bioRight Arrow Button Icon
Add Fortune on Google for similar content.

Latest in Politics

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 Politics

Trump undercuts GOP midterms message with snub of housing bill
PoliticsHousing
Trump undercuts GOP midterms message with snub of housing bill
By Katy O'Donnell and BloombergJuly 11, 2026
8 hours ago
Trump once suggested his Reflecting Pool renovations would last a century. It’s now being drained again after an algae bloom and peeling paint
PoliticsDonald Trump
Trump once suggested his Reflecting Pool renovations would last a century. It’s now being drained again after an algae bloom and peeling paint
By Will Weissert and The Associated PressJuly 11, 2026
9 hours ago
Iran’s supreme leader vows revenge for killing of his father after Trump threatens to launch thousands of missiles if Tehran tries to assassinate him
PoliticsIran
Iran’s supreme leader vows revenge for killing of his father after Trump threatens to launch thousands of missiles if Tehran tries to assassinate him
By Jon Gambrell, Michelle L. Price, Will Weissert and The Associated PressJuly 11, 2026
9 hours ago
Meet ‘Freedom Fuel Network’ stations, a new chain with cheaper gas and mysterious origins
EnergyDonald Trump
Meet ‘Freedom Fuel Network’ stations, a new chain with cheaper gas and mysterious origins
By Joshua HongJuly 10, 2026
1 day ago
At least a million woman lose access to humanitarian supports thanks to Trump budget cuts
PoliticsDonald Trump
At least a million woman lose access to humanitarian supports thanks to Trump budget cuts
By The Associated PressJuly 10, 2026
1 day ago
Vietnam is paying women to have more babies—but there’s a catch: they have to be on baby no. 2 to qualify for the $68 million budget
SuccessCareers
Vietnam is paying women to have more babies—but there’s a catch: they have to be on baby no. 2 to qualify for the $68 million budget
By Orianna Rosa RoyleJuly 10, 2026
2 days ago

Most Popular

U.S. Treasury has borrowed $155 billion every month of this fiscal year—and is now paying $24 billion a week in interest on its debts
Economy
U.S. Treasury has borrowed $155 billion every month of this fiscal year—and is now paying $24 billion a week in interest on its debts
By Eleanor PringleJuly 10, 2026
2 days ago
Top Iranian officials admitted to the supreme leader that the U.S. naval blockade was crushing the economy, report says, as Trump eyes reimposing it
Middle East
Top Iranian officials admitted to the supreme leader that the U.S. naval blockade was crushing the economy, report says, as Trump eyes reimposing it
By Jason MaJuly 10, 2026
1 day ago
Billionaire MacKenzie Scott just donated $20 million to support America’s youth mental health, as a fifth of teens struggle with suicidal thoughts
Success
Billionaire MacKenzie Scott just donated $20 million to support America’s youth mental health, as a fifth of teens struggle with suicidal thoughts
By Emma BurleighJuly 9, 2026
2 days ago
Wyoming officials say Meta’s 715,000-square-foot data center is responsible for contaminating its water system with a rare bacterium
Environment
Wyoming officials say Meta’s 715,000-square-foot data center is responsible for contaminating its water system with a rare bacterium
By Sasha RogelbergJuly 10, 2026
1 day ago
Americans are quietly abandoning the daily habit that billionaires say set them up for success—and it could have lasting consequences
Success
Americans are quietly abandoning the daily habit that billionaires say set them up for success—and it could have lasting consequences
By Preston ForeJuly 11, 2026
12 hours ago
'The first time ever in my career': Senior Citi executive on why the ultrawealthy want to diversify away from America
Banking
'The first time ever in my career': Senior Citi executive on why the ultrawealthy want to diversify away from America
By Nick LichtenbergJuly 11, 2026
12 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.