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

Trendingnow

1

I wrote that Boomers were choking America’s economy. Their responses to me were revealing

2

U.S. says deals with Iran for safe Hormuz transit are prohibited

3

Ex–Google CEO Eric Schmidt warns U.S. tech workers: Competing with China’s grueling 12-hour workdays means sacrificing work-life balance

1

I wrote that Boomers were choking America’s economy. Their responses to me were revealing

2

U.S. says deals with Iran for safe Hormuz transit are prohibited

3

Ex–Google CEO Eric Schmidt warns U.S. tech workers: Competing with China’s grueling 12-hour workdays means sacrificing work-life balance
FinanceTaxes

This Texas Tycoon Could Owe the IRS $2 Billion

By
Reuters
Reuters
Down Arrow Button Icon
By
Reuters
Reuters
Down Arrow Button Icon
January 5, 2016, 1:25 PM 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 is set to face off against the Internal Revenue Service at trial on Wednesday over more than $2 billion the agency says he owes for using offshore trusts to engage in one of the largest tax frauds in U.S. history.

The trial in federal bankruptcy court in Dallas comes nearly a year after Sam Wyly and his late brother Charles’ estate were ordered to pay the Securities and Exchange Commission $299.4 million for engaging in a massive securities fraud through those same trusts.

In the SEC case, a Manhattan jury in 2014 found the Wylys liable for scheming to hide from investors $550 million in trading profits in the stocks of four companies on whose boards they sat.

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

In April, the IRS filed claims asking the Wylys for a total of $3.22 billion in back taxes, penalties and interest, $2.03 billion of which is being sought from Sam Wyly.

Those claims, stemming from what the IRS has called one of the largest U.S. tax frauds, are now at the center of the trial before U.S. Bankruptcy Judge Barbara Houser.

The IRS says the Wylys starting in 1992 used a maze of trusts in the Isle of Man to evade paying taxes while exercising stock options and warrants they earned as directors of Sterling Software Inc, Michaels Stores Inc, Sterling Commerce Inc and Scottish Annuity & Life Holdings Ltd, now called Scottish Re Group Ltd.

The Wylys used the offshore system to fund business interests and to buy art, jewelry, and real estate, the IRS says.

The Wylys have denied engaging in fraud, saying they relied on lawyers who “thoroughly vetted” the offshore system, which was intended to allow them to defer, not avoid, taxes.

Stewart Thomas, outside general counsel for the Wyly family, called the IRS’s tax fraud claim “absurd,” and said the Wylys had “acted in good faith” and relied on the advice of numerous tax attorneys and accountants.

The IRS case mirrors the SEC lawsuit, which was filed in 2010 after years of civil and criminal investigations.

Both Wylys are expected to testify at the trial.

About the Author
By Reuters
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

Berkshire Hathaway to buy Taylor Morrison for $6.8 billion
Real Estatehome builders
Berkshire Hathaway to buy Taylor Morrison for $6.8 billion
By Paige Smith, Alexandre Rajbhandari and BloombergMay 31, 2026
1 hour ago
Wall Street may have solved a nagging mystery in global oil markets as doomsday scenarios have yet to arrive
EnergyOil
Wall Street may have solved a nagging mystery in global oil markets as doomsday scenarios have yet to arrive
By Jason MaMay 31, 2026
1 hour ago
A rare ‘super’ El Niño is looking more likely. Here’s what to expect
EnvironmentWeather and forecasting
A rare ‘super’ El Niño is looking more likely. Here’s what to expect
By Brian K. Sullivan and BloombergMay 31, 2026
3 hours ago
Data centers could help determine who wins the next war, and a shortage of compute would be ‘catastrophic,’ retired general says
AIMilitary
Data centers could help determine who wins the next war, and a shortage of compute would be ‘catastrophic,’ retired general says
By Jason MaMay 31, 2026
4 hours ago
Financial markets are losing the security blanket that’s bailed them out of trouble so many times, top economist warns 
EconomyMarkets
Financial markets are losing the security blanket that’s bailed them out of trouble so many times, top economist warns 
By Jason MaMay 31, 2026
7 hours ago
AI will make the ‘tech bro’ class even richer, Nobel laureate Joe Stiglitz says, just as it can take your job
AIJobs
AI will make the ‘tech bro’ class even richer, Nobel laureate Joe Stiglitz says, just as it can take your job
By Catherina GioinoMay 31, 2026
8 hours ago

Most Popular

I wrote that Boomers were choking America’s economy. Their responses to me were revealing
Personal Finance
I wrote that Boomers were choking America’s economy. Their responses to me were revealing
By Nick LichtenbergMay 31, 2026
13 hours ago
U.S. says deals with Iran for safe Hormuz transit are prohibited
Politics
U.S. says deals with Iran for safe Hormuz transit are prohibited
By Jack Wittels and BloombergMay 30, 2026
1 day ago
Ex–Google CEO Eric Schmidt warns U.S. tech workers: Competing with China’s grueling 12-hour workdays means sacrificing work-life balance
Future of Work
Ex–Google CEO Eric Schmidt warns U.S. tech workers: Competing with China’s grueling 12-hour workdays means sacrificing work-life balance
By Marco Quiroz-GutierrezMay 30, 2026
1 day ago
If Elon Musk merges SpaceX with Tesla he'll create a $3.4 trillion behemoth—with zero profits
Investing
If Elon Musk merges SpaceX with Tesla he'll create a $3.4 trillion behemoth—with zero profits
By Shawn TullyMay 31, 2026
17 hours ago
After a judge ordered Trump's name be removed from the Kennedy Center, president says it will 'soon be closed, probably never to open again'
Law
After a judge ordered Trump's name be removed from the Kennedy Center, president says it will 'soon be closed, probably never to open again'
By Collin Binkley and The Associated PressMay 30, 2026
1 day ago
After Blue Origin rocket explosion, NASA's entire moon exploration program depends on SpaceX for now as Musk eyes blockbuster IPO soon
Innovation
After Blue Origin rocket explosion, NASA's entire moon exploration program depends on SpaceX for now as Musk eyes blockbuster IPO soon
By Jason MaMay 30, 2026
1 day 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.