From Ford to Enron: Biggest Business Blunders

March 14, 2008— -- A wise man once said that those who fail to learn from history are doomed to repeat it.

Entrepreneurs will need every drop of hard-earned wisdom to navigate the coming year--by all accounts, a challenging one, care of a deepening credit crisis and potential recession.

With those dangers and the above adage in mind, we canvassed the last four centuries for the biggest business blunders of all time, in terms of wealth destroyed and opportunity lost.

Click here to learn more about big business blunders at our partner site, Forbes.com.

The stories span industries from technology to real estate. Market miscalculations, short-term thinking and rotten ethics are the broad themes. Taken together, the collective devastation of these miscues in current dollar value creeps into the trillions.

To be fair, some of these blunders were more unforeseen--and the blunderers more naturally disadvantaged--than others.

Take the Canarsee natives, who, in 1626, traded for trinkets a now rather stylish plot: Manhattan (then called New Amsterdam). The island fondly dubbed "the center of the universe" by many New Yorkers is now worth a cool $1 trillion, estimates Matthew Mondanile of Cushman & Wakefield, a global commercial real estate firm.

In another short-sighted deal, the Dutch later traded New Amsterdam to Great Britain in exchange for what is now the Republic of Suriname, a small country in South America with a wee gross domestic product of $2.9 billion.

Napoleon probably had more financial foresight than the Canarsees, but maybe not much. Back in 1803, the diminutive emperor was struggling to defend France's New World conquests, including Haiti, which was then in the midst of a slave revolt. Stretched thin but not willing to relinquish the island, Napoleon offered to sell the entire Louisiana Territory, rather than just the port of New Orleans, as had previously been discussed.

His offer: $15 million--3 cents per acre--or about $284 million today. The current value of that land, which now includes portions of 15 U.S. states and two Canadian provinces: about $750 billion, figures Mondanile. And Haiti? Less than a year after France inked the sale, Haiti won its independence.

OK, so it's hard to make objective decisions in the heat of battle. But what about when times are good and opportunities aplenty?

In the mid-1950s, Ford Motor, flush from its exceptionally successful Thunderbird, wanted to create a new model to compete head-to-head with General Motors' Oldsmobile. (The Ford Lincoln had served that purpose, but it was getting a makeover to go against GM's higher-end Cadillac.) Ford's solution: the Edsel, named after the son of founder Henry Ford.

Despite all the hype--including a television special called The Edsel Show--the Edsel proved to be one of the biggest bungles ever in the auto industry. Ford whiffed on three fronts: style (the car looked too much like other Ford models), size (too large, given the growing trend toward compact cars), and price (initially intended to be priced between a Lincoln and the lower-tier Mercury, the Edsel actually fell within Mercury's price point, and thus confused consumers). Ford sank $350 million (in 1950s dollars) into the Edsel before calling it quits; production of the model ceased Nov. 19, 1959.

Ford has since bounced back, but the lesson remains. "It's a classic case of perspective taking," says Adam Galinsky, a professor of management and organizations at Northwestern University's Kellogg School of Management. "If businesses don't consult outside perspectives to objectively assess consumers' demands, their products are at risk of failure."

Then there's Enron. The now infamous Houston-based energy company created offshore entities to hide huge losses--maneuvers that proved hard to uncover with even a careful read of its opaque financial statements. Analysts turned sour on the company in the summer of 2001; Enron filed for bankruptcy before year's end. The equity is now worthless, and key executives, including Chief Operating Officer Jeffrey Skilling and Chief Financial Officer Andrew Fastow, are doing jail time on charges including securities fraud and insider trading.

Is crumbling to deception and greed a blunder? It is when you consider that Enron was a legitimate energy company with real assets, like natural gas pipelines, before the insanity set in. Enron's collapse is also a catastrophic blunder when you consider the thousands of employees who had bet their retirements on now-worthless Enron stock.

And let's not forget the fallout from these frauds in the form of more burdensome regulation and higher costs for honest entrepreneurs. Indeed, the damage arguably extends far beyond the $78 billion in market value eviscerated in Enron's flameout.

The biggest blunderers of all time could well be the world's central bankers. Guys like U.S. Federal Reserve Chairman Ben Bernanke have the power to jump-start or derail entire economies by cranking the credit spigot open or closed.

Rubert Mundell, winner of the 1999 Nobel Prize in economics, has argued that "bungled monetary policy in the 1920s and 1930s caused chronic deflation [falling prices] and destabilized the world," writes author Charles Wheelan in his book Naked Economics.

Mundell's argument: "'Had the price of gold been raised in the late 1920s, or, alternatively, had the major central banks pursued policies of price stability instead of adhering to the gold standard, there would have been no Great Depression, no Nazi revolution, and no World War II.'"

Those are fighting words. With any luck, Bernanke and company won't earn a spot on this list.