• 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

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
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
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
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
Fortune Secondary Logo
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Leadership

Fortune Editor-in-Chief Alyson Shontell and Khosla Ventures Founder Vinod Khosla: Graphic for Fortune 500 Titans and Disruptors of Industry podcast. Episode title: "AI and the end of work?"
NewslettersCEO Daily
Famed investor Vinod Khosla predicts free AI labor will lead to an era of few jobs and great abundance
By Alyson ShontellMarch 4, 2026
2 hours ago
C-SuiteTech
3 questions every CEO needs to ask about the AI jobs doom loop in the wake of Jack Dorsey’s dramatic 40% layoffs at Block
By Diane BradyMarch 4, 2026
3 hours ago
Vinod Khosla, wearing a black suit jacket, looks forward.
AIFortune 500: Titans and Disruptors of Industry
OpenAI investor Vinod Khosla predicts today’s 5-year-olds won’t ever need to get jobs thanks to AI
By Sasha RogelbergMarch 4, 2026
3 hours ago
gen z
Commentarytourism
Millennials invented the experience economy and Gen Z is reinventing travel itself
By Nick LichtenbergMarch 4, 2026
4 hours ago
A woman sits in front of a laptop with her hands on her face.
AICareers
Gen Z is paying the price for lack of experience as AI takes their jobs. Older workers are safe—for now, Dallas Fed warns
By Jacqueline MunisMarch 4, 2026
5 hours ago
AOC
PoliticsElections
Obama’s former campaign manager has a ‘brutal truth’ for Democrats: ‘We have no economic message, and if we don’t get one, we’re not going to win’
By Meg Kinnard and The Associated PressMarch 3, 2026
17 hours ago

Most Popular

placeholder alt text
Economy
Interest on the $38.8 trillion national debt has tripled since 2020, and it already costs taxpayers more than defense and Medicaid
By Nick LichtenbergMarch 2, 2026
2 days ago
placeholder alt text
Middle East
Iran’s Islamic Revolutionary Guard controls a sprawling business empire that dominates the economy
By Jason MaMarch 2, 2026
2 days ago
placeholder alt text
Personal Finance
Current price of silver as of Tuesday, March 3, 2026
By Joseph HostetlerMarch 3, 2026
23 hours ago
placeholder alt text
Personal Finance
Current price of gold as of March 2, 2026
By Danny BakstMarch 2, 2026
2 days ago
placeholder alt text
AI
American schools weren’t broken until Silicon Valley used a lie to convince them they were—now reading and math scores are plummeting
By Sasha RogelbergMarch 1, 2026
3 days ago
placeholder alt text
Middle East
U.S. military gives Iran a taste of its own medicine with cheap copycat Shahed drones, while concern shifts to munitions supply in extended conflict
By Jason MaMarch 1, 2026
3 days 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.