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.