NEW YORK ( TheStreet) -- Every year on New Year's Eve they count down the seconds before dropping the ball in New York City's Times Square. Down here at the Five Dumbest Lab, we have a year-ending celebration of our own: We count down the 10 biggest moments on Wall Street where a CEO or company dropped the ball.Last week, we offered you
5. Michael & Me(Originally published 6/4/09) Michael Moore is enjoying the last laugh over GM's bankruptcy. But we are having the best laugh over his plan to turn the Motor City into Grand Central Station. Filmmaker and provocateur Michael Moore danced on GM's grave Monday, posting a letter to readers where he expressed "joy" over GM's demise. Writing from his hometown of Flint, Michigan, surrounded by "friends and family who are filled with anxiety about what will happen to them and to the town," Moore cranked the schadenfreude up to 10, reveling in the fact that his once powerful nemesis -- well, his first nemesis since he has now amassed quite a collection -- is now gone. One might think that Moore would cut the company a little slack considering it played such an instrumental role in launching his career. Twenty years ago, Moore shot to fame producing and starring in "Roger & Me," a documentary in which he illustrated the negative impacts of then-GM CEO Roger Smith's decisions to shut several auto plants in Flint.
4. Amazon.com Re-Kindles Orwell(Originally published 7/24/09) Somebody call the Thought Police! Amazon ( AMZN) stole my Kindle copy of 1984. The online bookseller enraged customers last Friday when it remotely deleted electronic editions of certain books already purchased by readers for their Kindle devices. Ironically, and quite hilariously, one of those books wiped out by Amazon was the George Orwell dystopian classic set in a nightmarish world in which speech is repressed by a dark, omnipresent overlord called Jeff Bezos ... oops, we mean Big Brother. Our bad.
3. Inept Insider Trading(Originally published 10/23/09) For such a wealthy, smart guy, Raj Rajaratnam looks like one poor, dumb criminal. Rajaratnam, the billionaire founder of the Galleon hedge fund, is alleged to have conspired with six other people to make illegal trades based on insider information that brought in $20 million in profits, according to a pair of criminal complaints filed in U.S. District Court in Manhattan last Friday. Some of those sketchy transactions involved shares of Google ( GOOG) and IBM ( IBM). Another score for Raj and his merry band of tipsters was Internet infrastructure provider Akamai Technologies ( AKAM), which they successfully shorted after receiving non-public earnings information from an unidentified person at the company. Too bad he allegedly blew it all -- and more -- on a failed attempt to game shares of chipmaker Advanced Micro Devices ( AMD).
2. So Long, CIT(Originally published 11/6/09) Move over Lehman Brothers, WorldCom, Washington Mutual and General Motors. You've got company. And U.S. taxpayers are picking up the tab. Small business lender CIT Group ( CIT) filed for Chapter 11 protection on Sunday, one of the five-largest bankruptcies in U.S. history. The company ultimately could not trim down its $10 billion of debt load following a failed debt exchange offer. According to its bankruptcy petition, CIT had $71 billion of assets and $64.9 billion of liabilities on June 30.