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

Yahoo shareholders still expect a massive Alibaba tax bill

By
Stephen Gandel
Stephen Gandel
Down Arrow Button Icon
By
Stephen Gandel
Stephen Gandel
Down Arrow Button Icon
September 29, 2015, 3:34 PM ET
Photograph by Ethan Miller — Getty Images

Yahoo’s Alibaba spin-off still has investors nervous.

On Monday night, the company announced that it would go ahead with its Alibaba spin-off, disregarding the fact that the IRS refused to say whether it would consider the spin-off tax free. Even so, Yahoo has said it believes it won’t have to pay Uncle Sam. And it has obtained a 100-page opinion from its outside law firm, Skadden, Arps, Slate, Meagher & Flom, written by a former top IRS lawyer to back up its claim. Independent tax expert Robert Willens told Fortune that he, too, thinks the spin-off will avoid taxation.

But one important group remains skeptical: Yahoo shareholders. Shares of the company rose just $0.88, or 3.2%, on the news of the spin-off. “People remain unconvinced, no question,” says Willens. “I would have expected the stock to increase a lot more than it has.”

The Yahoo-Alibaba saga has been somewhat of a slow motion train wreck for Yahoo CEO Marrisa Mayer. Yahoo holds 384 million shares of Alibaba, which is what’s left of an investment it made in the Chinese online retailer from years ago. It would like to sell those shares. But if Yahoo were to just go ahead and sell its stake, like any investor, it would owe capital gains taxes. So Yahoo (YHOO) came up with a clever way to avoid paying that bill: It decided to spin-off its Alibaba stake into a separate company, with existing shareholders getting the shares. Spin-offs are tax free as long as they have a business purpose. So, Yahoo said that it would spin off a division of its company that focuses on small business services along with its Alibaba (BABA) shares, creating a new company called Aabaco. However, Yahoo made it clear the small business unit it was shedding was not a very big operation. It was clear that the primary purpose of Aabaco would be to hold Yahoo’s Alibaba’s shares.

 

The deal got the attention of the IRS. And the regulator has been grumbling about the deal since at least mid-May. Earlier this month, the IRS said it wouldn’t bless the deal. An IRS official also recently said the agency is looking at closing the loophole that makes deals like Yahoo tax-free.

Since Yahoo has owned its Alibaba stake for a while, it’s hard to know what value investors put on it. That would give you a sense of how much they think Yahoo’s eventual tax bill might be now. Yahoo’s market cap rose by about $10 billion to just over $49 billion last October when the company started talking about the tax-free spin-off. Assume that jump was essentially the gain investors expected from not having to pay taxes. Since then, as the prospects of a tax-free spin off have dimmed, Yahoo’s shares have slumped, and its market cap is now $27 billion, or $22 billion less than what it was back in October. Alibaba’s shares have dropped as well during that time, erasing $14 billion from the value of Yahoo’s stake in the company. Yahoo also owns 35% of Yahoo Japan, and that stake has risen slightly in the same time, about 2%, which would tack another few hundred million on to the net worth of Yahoo.

That means Yahoo shareholders, even after the small jump in the stock price on Tuesday, are still putting Yahoo’s tax bill for its Alibaba shares at slightly more than $8 billion. That’s only a billion less than what Willens, the tax expert, estimates Yahoo’s tax bill would be if it were to abandon the spin-off and sell its shares outright.

Willens, though, thinks investors have got it wrong. He points out that the IRS has said that even if it closes the spin-off loophole, it won’t make its ruling retroactive. And the IRS isn’t likely to act in the next few months. Yahoo has said it plans to complete its spin-off by the end of the year. The IRS could still challenge the spin-off under the current rules and take Yahoo to court to force it to pay taxes. But Willens says Yahoo can point to several other similar deals that have never been challenged by the IRS. He thinks that would make it a tough case for the IRS to win.

Of course, there are some caveats to my math. Others things have happened in the past year. Stocks have fallen in general recently, which means investors may think that Yahoo is simply worth less than it used to be. What’s more, tax bill or not, Aabaco is likely to trade at a discount to Alibaba’s regular shares because of its weird spin-off structure.

Nonetheless, investors are assuming that Aabaco will trade at a big discount, and at least some of that could be on account of a whopper of a tax bill.

About the Author
By Stephen Gandel
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
  • 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
  • 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 Finance

The World Cup is supposed to be an economic windfall. But ‘you’re seeing a lot of headwinds’ now
North AmericaWorld Cup
The World Cup is supposed to be an economic windfall. But ‘you’re seeing a lot of headwinds’ now
By Marco Quiroz-GutierrezApril 4, 2026
2 hours ago
stressed student
Personal FinanceColleges and Universities
College grads in ‘AI-proof’ careers like psychology and education are seeing negative returns on their degrees
By Jake AngeloApril 4, 2026
3 hours ago
Scott Kupor sits at a table gesturing with both hands.
PoliticsLabor
The Trump administration is blurring the public and private sector workforce, and OPM director Scott Kupor won’t rule out conflict of interest risks
By Sasha RogelbergApril 4, 2026
5 hours ago
workers
AIdisruption
A Yale economist says AGI won’t automate most jobs—because they’re not worth the trouble
By Nick LichtenbergApril 4, 2026
6 hours ago
MUSCAT, OMAN - Locals visit Muscat Anchorage near the Strait of Hormuz on March 30, 2026 in Muscat, Oman. Several Chinese-owned vessels were reportedly able to transit the Strait of Hormuz today, the day after U.S. President Donald Trump said Iran would allow 20 ships to cross through the vital waterway. (Photo by Elke Scholiers/Getty Images)
EnergyIran
Iran’s military may be decimated, but it’s winning the energy war as it controls who gets cargoes through the Strait of Hormuz
By Jordan BlumApril 4, 2026
7 hours ago
rick steves holds american flag
PoliticsTaxes
Travel guru Rick Steves is happy to pay more taxes
By Catherina GioinoApril 3, 2026
15 hours ago

Most Popular

Google CEO Sundar Pichai says we’re just a decade away from a new normal of extraterrestrial data centers
Innovation
Google CEO Sundar Pichai says we’re just a decade away from a new normal of extraterrestrial data centers
By Fortune EditorsApril 3, 2026
1 day ago
Gen Z fled San Francisco for Texas and Florida. Now they’re turning ‘welcomer cities’ into the next big tech towns
Real Estate
Gen Z fled San Francisco for Texas and Florida. Now they’re turning ‘welcomer cities’ into the next big tech towns
By Fortune EditorsApril 2, 2026
2 days ago
The Walmart billionaires next door: Quiet backlash is brewing against the heirs who remade the retailer’s hometown
Magazine
The Walmart billionaires next door: Quiet backlash is brewing against the heirs who remade the retailer’s hometown
By Fortune EditorsApril 3, 2026
1 day ago
Current price of oil as of April 3, 2026
Personal Finance
Current price of oil as of April 3, 2026
By Fortune EditorsApril 3, 2026
1 day ago
Current price of silver as of Friday, April 3, 2026
Personal Finance
Current price of silver as of Friday, April 3, 2026
By Fortune EditorsApril 3, 2026
1 day ago
Major 4-day workweek study suggests that when we work 5 days we spend one doing basically nothing
Success
Major 4-day workweek study suggests that when we work 5 days we spend one doing basically nothing
By Fortune EditorsApril 2, 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.