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

This Texas Tycoon Just Lost a $1 Billion IRS Tax Case

By
Reuters
Reuters
Down Arrow Button Icon
By
Reuters
Reuters
Down Arrow Button Icon
May 11, 2016, 5:05 AM ET
American Renewable Energy Day - Day 2
ASPEN, CO - AUGUST 21: Sam Wyly attends the panel: "Putting Wealth to Work in the New Clean Energy Economy "on day 2 of the American Renewable Energy Day on August 21, 2010 in Aspen, Colorado. (Photo by Riccardo S. Savi/Getty Images)Photograph by Riccardo S. Savi — Getty Images

Texas tycoon Sam Wyly engaged in “deceptive and fraudulent actions” in a years-long scheme to dodge taxes on more than $1 billion held in offshore trusts, a federal bankruptcy judge ruled on Tuesday.

U.S. Bankruptcy Judge Barbara Houser ruled that there was “clear and convincing evidence” against Wyly who will be required to pay, according to the Texas Law Book, as much as $1.4 billion in back taxes and penalties.

The Internal Revenue Service (IRS) had initially sought $3.22 billion in back taxes, penalties and interest from Wyly and Caroline Wyly, the widow of his late brother Charles, in a trial that opened at the federal bankruptcy court in Dallas earlier this year.

The IRS later reduced its claims, saying it was now seeking $1.43 billion from Sam Wyly and $834.2 million from Caroline Wyly.

The IRS claimed the Wylys, through a sheme that dated back to 1992, used offshore trusts to avoid paying taxes on $1.1 billion while exercising stock options and warrants of four companies on whose boards the brothers sat.

“The Court is convinced—by clear and convincing evidence—that Sam and Charles committed tax fraud,” Houser wrote, adding that Caroline was unaware of the scheme and was innocent.

The Wylys argued that they relied on a network of advisors and lawyers who vetted the offshore system and advised them on their taxes.

“Sam knew what was happening in connection with the offshore system and that no money or assets moved within that system without Sam’s knowledge and express direction,” Houser wrote. “He does not simply turn his wealth over to others and wish them luck.”

The ruling came nearly a year after Sam Wyly and Charles’ estate were ordered to pay the U.S. Securities and Exchange Commission $299.4 million for engaging in securities fraud through those same trusts.

In that case, a Manhattan jury in 2014 found the Wylys liable for scheming to hide $550 million in trading profits in the stocks of Sterling Software, Michaels Stores (MIK), Sterling Commerce Inc and Scottish Annuity & Life Holdings, now called Scottish Re Group (SKRUF).

Following that verdict, Sam Wyly, who last appeared on Forbes’ list of the 400 richest Americans in 2010 with a net worth of $1 billion, and Caroline Wyly filed for bankruptcy in October 2014. Charles Wyly died in a car crash in 2011.

About the Author
By Reuters
See full bioRight Arrow Button Icon

Latest in Leadership

Nicholas Thompson
C-SuiteBook Excerpt
I took over one of the most prestigious media firms while training for an ultramarathon. Here’s what I learned becoming CEO of The Atlantic
By Nicholas ThompsonDecember 13, 2025
20 hours ago
Lauren Antonoff
SuccessCareers
Once a college dropout, this CEO went back to school at 52—but she still says the Gen Zers who will succeed are those who ‘forge their own path’
By Preston ForeDecember 13, 2025
21 hours ago
Asiathe future of work
The CEO of one of Asia’s largest co-working space providers says his business has more in common with hotels
By Angelica AngDecember 12, 2025
1 day ago
Donald Trump
HealthHealth Insurance
‘Tragedy in the making’: Top healthcare exec on why insurance will spike to subsidize a tax cut to millionaires and billionaires
By Nick LichtenbergDecember 12, 2025
2 days ago
three men in suits, one gesturing
AIBrainstorm AI
The fastest athletes in the world can botch a baton pass if trust isn’t there—and the same is true of AI, Blackbaud exec says
By Amanda GerutDecember 12, 2025
2 days ago
Brainstorm AI panel
AIBrainstorm AI
Creative workers won’t be replaced by AI—but their roles will change to become ‘directors’ managing AI agents, executives say
By Beatrice NolanDecember 12, 2025
2 days ago

Most Popular

placeholder alt text
Success
Apple cofounder Ronald Wayne sold his 10% stake for $800 in 1976—today it’d be worth up to $400 billion
By Preston ForeDecember 12, 2025
2 days ago
placeholder alt text
Economy
Tariffs are taxes and they were used to finance the federal government until the 1913 income tax. A top economist breaks it down
By Kent JonesDecember 12, 2025
2 days ago
placeholder alt text
Success
40% of Stanford undergrads receive disability accommodations—but it’s become a college-wide phenomenon as Gen Z try to succeed in the current climate
By Preston ForeDecember 12, 2025
2 days ago
placeholder alt text
Economy
The Fed just ‘Trump-proofed’ itself with a unanimous move to preempt a potential leadership shake-up
By Jason MaDecember 12, 2025
1 day ago
placeholder alt text
Success
Apple CEO Tim Cook out-earns the average American’s salary in just 7 hours—to put that into context, he could buy a new $439,000 home in just 2 days
By Emma BurleighDecember 12, 2025
2 days ago
placeholder alt text
Economy
For the first time since Trump’s tariff rollout, import tax revenue has fallen, threatening his lofty plans to slash the $38 trillion national debt
By Sasha RogelbergDecember 12, 2025
2 days ago
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • 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
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map

© 2025 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.