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

Zell’s legacy lives on: IRS goes after Tribune

By
Allan Sloan
Allan Sloan
Down Arrow Button Icon
By
Allan Sloan
Allan Sloan
Down Arrow Button Icon
June 18, 2013, 1:00 PM ET
Sam Zell, chairman of Equity Group Investments, appears on a Fox Business Network's show in New York
Sam Zell, chairman of Equity Group Investments, appears on Fox Business Network's show "Opening Bell with Maria Bartiromo" in New York June 10, 2014. REUTERS/Brendan McDermid (UNITED STATES - Tags: BUSINESS) - RTR3T3ZQBrendan McDermid — Reuters

Sam Zell is gone from the Tribune (TRCO), but his toxic financial legacy lives on. Not only did his debt-fueled purchase of one of the nation’s biggest media companies help precipitate its bankruptcy, costing creditors billions and wiping out thousands of jobs, but he has left a nasty tax mess behind for Tribune, which exited Chapter 11 proceedings on Dec. 31.

As I predicted several years ago, the Internal Revenue Service has challenged the tacky tax-avoiding way that Zell had Tribune unload Newsday, a Long Island, N.Y. newspaper, and it seems virtually certain to challenge the way that Tribune unloaded the Chicago Cubs.

By the time the final papers are shuffled, the IRS and local tax authorities are likely to be seeking considerably more than half a billion dollars in taxes, penalties, and interest from Tribune in regard to what I call the “non-sale sales” of the Cubs and Newsday.

Before we proceed, a bow to tax expert Bob Willens of Robert Willens LLC, who told his clients that he expected both the Cubs and the Newsday deal to be challenged.

Willens’s newsletter reported Monday that the IRS had rejected the tax treatment Tribune had sought for the Newsday deal. This led me to a Tribune financial report that was issued Monday. Guess what? Buried in the tax footnotes, Tribune (which declined comment) said that the IRS is seeking $190 million of taxes and a $38 million “accuracy-related penalty” for not treating the 2008 Newsday transaction as a sale. In addition, Tribune said, it could be liable for $17 million of interest to the IRS, and $28 million of taxes and interest to other taxing authorities. Total exposure: $273 million.

MORE: Introducing: The kid VC

Tribune also said that its return for 2009, the year it unloaded the Cubs, is being audited, and a challenge to the Cubs deal could cost $225 million plus interest and penalties. Apply the same penalties as the IRS is seeking in the Newsday deal, and the total exposure is about $300 million.

In its tax footnote, Tribune says that it “disagrees with the IRS position (about Newsday) and will request that the IRS administrative appeals office review the issue.” That would explain why Tribune says it had no reserves set aside for Cubs or Newsday-related tax liability.

I find this amazingly optimistic on Tribune’s part, considering how gamy the transactions were. In the Newsday transaction, Zell — who boasts about his tax-avoiding skills at every opportunity — had Tribune contribute Newsday to a partnership to which Cablevision (CVC), the big Long Island cable TV outfit, contributed $650 million of promissory notes. Tribune emerged with $630 million in cash. Cablevision emerged with 97.14529% of Newsday. And somehow, we — and the IRS — were supposed to believe this wasn’t a sale.

Zell played a similar game with the Cubs, contributing the team to a partnership with the Ricketts family of TD Ameritrade fame, which contributed $740 million. Tribune emerged with $705 million, the Ricketts family emerged with 95% of the Cubs.

MORE: Ben Bernanke threatens private equity

These deals smelled so awful that when they were made, Bob Willens was telling his clients he expected the IRS to challenge them. That’s now happened with the Newsday deal, and seems to be on tap for the Cubs deal.

I used to have a reasonably congenial relationship with Zell, who named himself the Gravedancer because he specialized in buying distressed properties that had been left for dead. I even ended up as a minor character in an artwork he commissioned to commemorate a 1992 tax-avoiding deal. He placed me in the lowest circle of hell and purposely misspelled my name.

I used to consider Zell and his tax avoidance schemes sort of amusing. But the amusement — and congeniality — are both long gone.

I’m sure that after litigation or the threat of it, Tribune will ultimately settle considerably less than the $600 million likely total of the claims, penalties and interest. However, my bet is that Tribune will ultimately fork over more than $100 million to pay for the tax games Zell played with Newsday (one of my former employers) and the Cubs.

That’s just what the company, struggling to survive in a hostile landscape for media companies, needed in its new life — a big, fat tax bill from the past. Thanks a lot, Sam.

About the Author
By Allan Sloan
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

Tim Cook reveals the advice he gave Apple’s next CEO: The most important decision he’ll make is ‘where he spends his time’
Big TechApple
Tim Cook reveals the advice he gave Apple’s next CEO: The most important decision he’ll make is ‘where he spends his time’
By Alexei OreskovicApril 30, 2026
6 hours ago
Moreno gestures with his hand
PoliticsU.S. Senate
A ‘no-brainer’: Senate unanimously bans members and staff from using prediction markets
By Mary Clare Jalonick and The Associated PressApril 30, 2026
10 hours ago
Kevin Warsh, nominee for chairman of the Federal Reserve.
BankingFederal Reserve
Former Fed economist raises alarm on Warsh after historically partisan vote: ‘this is not normal is going to be a theme’
By Eva RoytburgApril 30, 2026
10 hours ago
A banner depicting portraits of Iran's late Supreme Leader Ayatollah Ali Khamenei and Ayatollah Mojtaba Khamenei
PoliticsIran
Iranian supreme leader says the only place Americans belong in the Gulf is ‘at the bottom of its waters’
By Jon Gambrell, Aamer Madhani and The Associated PressApril 30, 2026
10 hours ago
Wind energy CEO says company ‘must adapt’ as Trump offers $2 billion to kill offshore wind projects
EnergyU.S. Politics
Wind energy CEO says company ‘must adapt’ as Trump offers $2 billion to kill offshore wind projects
By Marco Quiroz-GutierrezApril 30, 2026
12 hours ago
Lithium battery facility
North AmericaChina
China dominates the world’s lithium supply. The U.S. just found 328 years’ worth in its own backyard
By Jake AngeloApril 30, 2026
13 hours ago

Most Popular

Apple cofounder Ronald Wayne—whose stake would be worth up to $400 billion had he not sold it in 1976—says that at 91, he has no regrets
Success
Apple cofounder Ronald Wayne—whose stake would be worth up to $400 billion had he not sold it in 1976—says that at 91, he has no regrets
By Preston ForeApril 27, 2026
4 days ago
Google Cloud revenue is now 18% of Alphabet's business. Is this the beginning of the end of Google's search identity?
Big Tech
Google Cloud revenue is now 18% of Alphabet's business. Is this the beginning of the end of Google's search identity?
By Alexei OreskovicApril 29, 2026
1 day ago
China dominates the world's lithium supply. The U.S. just found 328 years' worth in its own backyard
North America
China dominates the world's lithium supply. The U.S. just found 328 years' worth in its own backyard
By Jake AngeloApril 30, 2026
13 hours ago
With no end in sight, Trump considers new options in Iran war—including the ‘Dark Eagle’ hypersonic missile
Big Tech
With no end in sight, Trump considers new options in Iran war—including the ‘Dark Eagle’ hypersonic missile
By Jim EdwardsApril 30, 2026
21 hours ago
‘The cost of compute is far beyond the costs of the employees’: Nvidia executive says right now AI is more expensive than paying human workers
AI
‘The cost of compute is far beyond the costs of the employees’: Nvidia executive says right now AI is more expensive than paying human workers
By Sasha RogelbergApril 28, 2026
3 days ago
Accenture's Julie Sweet blew up 50 years of company history. She says the hardest part is still ahead
Conferences
Accenture's Julie Sweet blew up 50 years of company history. She says the hardest part is still ahead
By Nick LichtenbergApril 29, 2026
2 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.