Two of the Worst Losses in Business History

On this day in economic and financial history...

The largest civil-damage award in business history was first rendered in 1985 in the case of v. Pennzoil. However, it was far from certain that the $10.53 billion judgment would stand on appeal -- until, on Feb. 12, 1987, a Texas court of appeals upheld the original $7.53 billion award for actual damages and reduced punitive damages from $3 billion to $1 billion. Texaco was on the hook for $8.53 billion, an amount far exceeding its cash on hand. The source of Texaco's problems, as is often the case, began with a business deal that went very, very wrong.

Three years earlier, the chairman of privately held Pennzoil and the son of Getty Oil's founder had agreed to Pennzoil's offer of $110 per share for 43% of Getty Oil in a preliminary $5.3 billion merger agreement. Less than a week after reaching this deal, Getty's board approved a deal with Texaco instead, which had jumped in with a $10.2 billion offer for the entire company. Pennzoil sued Texaco for interfering with what it felt was a legally binding contractual agreement, and the Texas courts twice agreed. The verdict pushed Texaco into bankruptcy two months later, making it then the largest company in U.S. history to seek bankruptcy protection. As Martin Klein of the American Bar Association's bankruptcy subcommittee said at the time, "Pennzoil is in a better position [after the verdict] than it would have been if the merger had gone through."


A year later, bold activist investor Carl Icahn of Icahn Enterprises brokered an initial $3 billion settlement between the two parties that allowed Texaco to exit bankruptcy. This wasn't altruistic: Icahn, who had formed his company at the same time the courts decided Texaco's appeal, owned nearly 15% of the oil company's stock and made a killing off of its post-bankruptcy rebound. Texaco and Chevron merged in 2001, and Texaco learned its lesson the second time around -- no one felt slighted enough by that deal to sue.

Step into my FedEx Office
On Feb. 12, 2004, FedEx made its big move into the retail space by finalizing an acquisition of privately held Kinko's for $2.4 billion. The shipping giant had big plans to create a network of linked one-stop stores for business printing and shipping, which must have been at least in part a response to rival UPS' acquisition and rebranding of the similarly positioned Mail Boxes Etc. three years earlier. At the time, Kinko's had about 1,200 locations to the UPS Store's roughly 3,000, so FedEx had a little bit of catching up to do.

FedEx initially planned to maintain the Kinko's name, but after four years of rough going, the company decided to rebrand its retail stores as FedEx Office, which resulted in a one-time write-off of almost $900 million. The growing irrelevance of print services in an era of cheap and nearly ubiquitous printers and copiers, compounded by the difficulties of operating through the Great Recession, forced FedEx to shutter its Office locations in Australia, Mexico, China, Japan, and the United Kingdom. Despite these setbacks, FedEx Office now maintains more than 1,900 interconnected locations -- still a far cry from the UPS Store's 4,700 franchises.

That's a lot of red ink
No matter how strong a company is, it can only suffer so many losses before requiring outside help or going bankrupt. The story of how General Motors eventually sought both of those can be traced to its 2007 annual report, which revealed a staggering $38.7 billion loss for the year when it was released on Feb. 12, 2008.

Despite a narrow fourth-quarter profit of $46 million (mostly due to tax benefits), the automaker still set an industry record for annual losses. This was only partly due to one-time charges, such as the buyouts of 19,000 hourly workers and $2.8 billion in liabilities stemming from former auto-parts division Delphi, which had been spun off years earlier and which had suffered its own financial problems leading up to the global crisis. Skyrocketing gas prices and economic weakness had put a double whammy on the American auto industry, and as its largest representative, GM felt the pain most acutely. Its North American revenue plummeted by nearly $10 billion in the second quarter alone. Despite sales of 9.4 million vehicles, GM's revenue still plunged to $181 billion, a 12% drop from 2006.

This report came only four months after the Dow Jones Industrial Average reached its all-time high of 14,165 points, and it was one of the clearest signals yet that the U.S. economy was on shaky ground. In those four months, the index had lost 13% of its value. An investor who escaped the market that day after hearing about GM's woes would have avoided the 47% drop to come, but virtually no one would have the impeccable timing to avoid the worst of the Great Recession.

Unable to continue its current employment practices profitably, GM took the unprecedented step of offering its entire U.S. hourly workforce lucrative contract buyouts, which could amount to as much as $140,000 for 10-year veterans willing to forgo future pension and health care coverage. None of GM's efforts could stave off further losses, which amounted to another $30.9 billion in 2008. By mid-2009, GM had filed for bankruptcy. A combined $67 billion in bailout funds have been injected into GM and its former finance arm, GMAC (now Ally Financial), of which $31 billion remained outstanding five years after GM reported its record loss. However, all is not lost. GM's 2011 net income amounted to $7.6 billion -- a record annual profit earned only four years after a record-breaking loss.

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The article Two of the Worst Losses in Business History originally appeared on Fool.com.

Fool contributor Alex Planes holds no financial position in any company mentioned here. Add him on Google+ or follow him on Twitter @TMFBiggles for more insight and occasional attempts at comedy. The Motley Fool recommends Chevron, FedEx, General Motors, and United Parcel Service. Try any of our Foolish newsletter services free for 30 days. We Fools may not all hold the same opinions, but we all believe that considering a diverse range of insights makes us better investors. The Motley Fool has a disclosure policy.

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