For people who have gone through a change in millennium, the mere entrance of a new decade may not seem like much. But what a decade! Why, has anyone ever seen anything so awful?

Think of all the “worsts” that blessed the business world since 2000: worst stock-market performance, worst scandals, worst companies, worst CEOs, worst regulators, and, all too often, worst journalism. We missed a lot, but then again, we were part of the decade’s agony (see No. 10).

So in compiling this list of the top-10 biggest stories of the decade, I had a great deal of big and usually bad news to choose from, and some of gaudier stories of the decade didn’t make the cut. Martha Stewart's trip to prison didn’t make the cut, and neither did Dick Grasso's nine-figure paycheck. Sure, there were smatterings of good news here and there, but they got muscled out by the Big Terrible (No. 1) and its accomplices.

So here they are, in inverse order of importance:

10. The Death of Old Media

As the decade began, AOL was merging with Time Warner in what was widely heralded as an indication of the future for old-fashioned paper-and-ink media properties. It was a sign of the future—as in “funeral.” By 2009, AOL was de-merging from Time Warner, and the old media were in a state of disintegration. Magazines shuttered, and newspapers were on the endangered-species list. The formerly august Miami Herald was actually asking for reader contributions. The 1980s newspaper film Absence of Malice today would have the title Absence of Advertisers.

9. Automakers Go Bust

In any other decade, the bankruptcy of two of the Big Three automakers, General Motors and Chrysler, would be the defining events of an epoch. In this decade, they rate also-ran status. It was hardly earth-shattering news that the Big Three were failing to make cars Americans wanted to buy, after all. In a sense, this was just the dénouement of four decades of mismanagement and decay.

8. Enron and Friends

Jeff Skilling, his cohorts at Enron, and all the other corporate bad actors of the first half of the decade—John Rigas of Adelphia Communications, Dennis Kozlowski of Tyco International, and their counterparts at Global Crossing and WorldCom—made people mad as hell. Until, that is, they stopped being mad and forgot about the whole thing. Sarbanes-Oxley was passed to prevent it from ever happening again. By the end of the decade, it was all ancient history and Sox was being dismantled.

7. Bernard Madoff

The corporate scandals of yore could not compete with the man who is arguably the worst financial criminal in history. Madoff stole more, over a longer period of time, than anyone since the Spaniards robbed the Incas. But look where he stands on the list: Lots worse to come.

6. The Real Estate Bubble

The all-American act of buying a house became a crucial part of a gargantuan pump-and-dump scheme. Take overvalued assets, combine with predatory lending and Wall Street bankers selling toxic derivatives to uninformed institutional investors based on absurd credit ratings, and one has the ingredients for a pretty wild crash.