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

Exclusive

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

FinanceInvesting

The dumbest deals of 2013

By
Stephen Gandel
Stephen Gandel
Down Arrow Button Icon
By
Stephen Gandel
Stephen Gandel
Down Arrow Button Icon
December 24, 2013, 6:12 AM ET

Caterpillar-ERA Mining Machines

Caterpillar mining equipment.

Caterpillar has long wanted a bigger presence in China. It's acquisition of ERA, a China-based manufacture of mining machines, didn't help. In January, Caterpillar (CAT) was forced write-off $580 million, or 90% of what it paid for the deal. Sales at ERA has been inflated by a long-running accounting fraud at one of its divisions. And Caterpillar was duped into thinking the company was worth much more than it actually was. Other U.S. companies had considered buying ERA before Caterpillar, but balked. Caterpillar might want to hire some of their advisors.

OfficeMax-Office Depot

Perhaps they should have gone with Michael Scott. When Office Depot announced its merger with OfficeMax in February, the companies left open which of their CEOs would end up leading the combined office supply chain. In the end, the search committee decided neither was qualified. Worse, it seemed no one else wanted the job either. When the deal was completed in early November, Office Depot (ODP) still hadn't found a new CEO. Eventually, the company went with Roland Smith, who came from the grocery business, and had once been the head of Wendy's. Also complicating the merger was the fact that the Federal Trade Commission considered blocking the deal. Back in 1996, the FTC had put the kibosh on a deal between Office Depot and Staples for anti-trust reasons. This time around the FTC announced that after a lengthy investigation the agency concluded that both Office Depot and Office Max were losing sales to online competitors and lacked the ability to raise prices above Wal-Mart (WMT). Even non-superstore competitors, the FTC determined, regularly take business from Office Depot and OfficeMax. So thumbs up guys.

Prosena

Prosena

It was generally a good year for IPOs, but it was not without duds. Dutch biotech company Prosensa raised $80 million in a June IPO. Its shares soared 154% in the first month of trading, despite the fact that most of the company's prospects were based on one muscular dystrophy drug. In mid-September, the FDA said that a late stage trial had revealed that the drug, drisapersen, was not significantly better than a placebo. Prosensa's stock plunged 70% in one day. It now trades for $4.86, far below its IPO price of $13.

It was generally a good year for IPOs, but it was not without duds. Dutch biotech company Prosensa (RNA) raised $80 million in a June IPO. Its shares soared 154% in the first month of trading, despite the fact that most of the company's prospects were based on one muscular dystrophy drug. In mid-September, the FDA said that a late stage trial had revealed that the drug, drisapersen, was not significantly better than a placebo. Prosensa's stock plunged 70% in one day. It now trades for $4.86, far below its IPO price of $13.

Apax-Rue21

Apax-Rue21

Apax Partners may have taken its long-time crush on teen retailer Rue21 a little too far. In mid-May, the private equity firm said it was re-buying the retailer for $1.1 billion, paying roughly twice what Apax had sold the company for in an IPO four years earlier. Within a few months, though, the deal was struggling. Rue21's summer and fall lines didn't sell as well as expected. Same-store sales fell nearly 10%. That rattled investors, who didn't want to buy the bonds to finance the deal. Apax's bankers, including Bank of America, JPMorgan Chase, and Goldman Sachs, had trouble selling the debt to back the deal. Apax eventually completed the deal, but some question whether the teen retailer will generate enough cash flow to pay for all the debt Apax took on to acquire the company, particularly if sales continue to drop. It's a hot mess.

Apax Partners may have taken its long-time crush on teen retailer Rue21 a little too far. In mid-May, the private equity firm said it was re-buying the retailer for $1.1 billion, paying roughly twice what Apax had sold the company for in an IPO four years earlier. Within a few months, though, the deal was struggling. Rue21's summer and fall lines didn't sell as well as expected. Same-store sales fell nearly 10%. That rattled investors, who didn't want to buy the bonds to finance the deal. Apax's bankers, including Bank of America (BAC), JPMorgan Chase (JPM), and Goldman Sachs (GS), had trouble selling the debt to back the deal. Apax eventually completed the deal, but some question whether the teen retailer will generate enough cash flow to pay for all the debt Apax took on to acquire the company, particularly if sales continue to drop. It's a hot mess.

Microsoft-Nokia

Microsoft's acquisition prowess is legendary in its awfulness. And 2013 offered more evidence of that. Microsoft (MSFT) spent $7 billion for Nokia, marrying the fledgling Windows mobile software with the maker of 2005's hottest flip phone. Nokia has been losing market share for years. And it will add 32,000 employees and $700 million in costs in the first year alone to an already bloated Microsoft. Barron's said the Nokia deal keeps "Microsoft's reputation for overpaying for big acquisitions" in tact. Influential tech analyst Rick Sherland called it the deal "not even a mother could love."

BlackBerry

BlackBerry

Awkward. In August BlackBerry's CEO Thornsten Heins said the maker of e-mail friendly cellphones was up for sale. But three months later, the deal was off, and Heins was out of a job. BlackBerry failed to get much interest, signaling to the world that the company might be in even worse shape than many thought. The company's shares plunged 16% after BlackBerry said there would be no deal.

Awkward. In August BlackBerry's CEO Thornsten Heins said the maker of e-mail friendly cellphones was up for sale. But three months later, the deal was off, and Heins was out of a job. BlackBerry (BBRY) failed to get much interest, signaling to the world that the company might be in even worse shape than many thought. The company's shares plunged 16% after BlackBerry said there would be no deal.

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
  • 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

John Ketchum, CEO of NextEra Energy, speaks during BlackRock's 2026 Infrastructure Summit in Washington, DC, on March 11, 2026. Photographer: Daniel Heuer/Bloomberg via Getty Images
EnergyNextEra Energy
NextEra’s $67 billion Dominion takeover creates the world’s largest utility—just in time to win the AI data-center power surge
By Jordan BlumMay 18, 2026
49 minutes ago
Employers are quietly pausing 401(k) matches again. The last time this happened was the 2008 recession and Covid
Personal Finance401(k)
Employers are quietly pausing 401(k) matches again. The last time this happened was the 2008 recession and Covid
By Courtney Vinopal and HR BrewMay 18, 2026
51 minutes ago
Harvard University banners hang in front of a building
CryptoCryptocurrency
Harvard sold off its entire $87 million Ethereum stake just one quarter after buying it
By Jack KubinecMay 18, 2026
1 hour ago
Interior view of the New York Stock Exchange
Economyinvestors
New York Fed warns about $69 trillion foreign investment ‘burden’ on U.S. economy
By Tristan BoveMay 18, 2026
2 hours ago
President Donald Trump speaks to the media aboard Air Force One on May 15, 2026.
EconomyDonald Trump
While Trump insisted the Iran war would end ‘soon,’ an account in his name was buying millions in oil, defense and gold
By Eva RoytburgMay 18, 2026
3 hours ago
Ryanair’s CFO says the airline has plans for an ‘armageddon situation’ as the jet fuel crisis threatens weaker European airlines this winter
EnergyAirline industry
Ryanair’s CFO says the airline has plans for an ‘armageddon situation’ as the jet fuel crisis threatens weaker European airlines this winter
By Marco Quiroz-GutierrezMay 18, 2026
3 hours ago

Most Popular

The top foreign holders of U.S. debt may soon dump Treasury bonds and bring their money back home, potentially spiking borrowing costs
Economy
The top foreign holders of U.S. debt may soon dump Treasury bonds and bring their money back home, potentially spiking borrowing costs
By Jason MaMay 17, 2026
1 day ago
Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI
AI
Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI
By Jake AngeloMay 16, 2026
2 days ago
The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
Politics
The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
By Jake AngeloMay 12, 2026
6 days ago
'No one was coming to save me': How Reese Witherspoon built a $900 million company from a problem Hollywood wouldn't fix
Success
'No one was coming to save me': How Reese Witherspoon built a $900 million company from a problem Hollywood wouldn't fix
By Sydney LakeMay 17, 2026
1 day ago
SpaceX heads into a record-shattering IPO with the 'deepest moat that exists today' as investors vow to 'never bet against Elon'
Innovation
SpaceX heads into a record-shattering IPO with the 'deepest moat that exists today' as investors vow to 'never bet against Elon'
By Jason MaMay 16, 2026
2 days ago
Mamdani's New York is coming to tax your private jet. Here's how to prepare
Personal Finance
Mamdani's New York is coming to tax your private jet. Here's how to prepare
By Greg RaiffMay 16, 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.