The Decade's 10 Worst Career Moves

Heidi Gutman, NBC NewsWire / AP Photo

Heidi Gutman, NBC NewsWire / AP Photo

Eliot Spitzer

Lesson: If you’re going to cheat on your wife, don’t be a hypocrite

Before he was known as Client No. 9, Eliot Spitzer built his career by taking down Manhattan’s organized crime as New York’s attorney general. It led to the governor’s mansion. But after his misdeeds (in socks) with prostitutes became public, he resigned within hours. At least the hooker in question, Ashley Dupre, did OK: She’s now an advice columnist.

Andy Kropa / AP Photo

Mischa Barton

Lesson: If it ain’t broke….

In its first season on Fox in 2004, teen angst drama The O.C. averaged 9.7 million viewers, but by 2006 star Mischa Barton wanted out. "My character has been through so, so much and there's really nothing more left for her to do,” she said. She had a fledgling film career and a Keds endorsement contract to keep her occupied, but neither lasted very long. A recent return to the small screen didn’t revive her career, either. The Beautiful Life was canceled this fall after just two episodes. Paging Shelley Long…

Davis Turner / Getty Images

Mark Sanford

Lesson: If you’re going to cheat on your wife, don’t lie to your constituents.

Finding his “soul mate” cost Mark Sanford his career. Sanford, the governor of South Carolina, told the world he was “hiking the Appalachian Trail” but instead retreated to Argentina to visit his mistress for six days in June without alerting his family, staff, or security. Predictably, the lapse caused public outrage and investigations into whether Sanford used state funds to finance the romantic affair. Impeachment was threatened, but the South Carolina House Judiciary Committee chose to censure the governor instead. In January, he’ll face the State Ethics Commission.

Ross Kinnaird / Getty Images

Tiger Woods

Lesson: If you’re going to cheat on your wife, try to stay in single digits

Tiger Woods made $1 billion from his winning, pristine image. But the car wreck-sparked revelation that Tiger had apparently been involved in extramarital affairs for years with at least dozen women shattered his facade. His statement, “I have let my family down and I regret those transgressions with all of my heart,” didn’t do much to engender support. Gillette shelved its advertising campaigns and Accenture canceled its sponsorship. Wife Elin is reportedly seeking a divorce.

WHAT WERE THE 10 BEST CAREER MOVES OF THE DECADE? CLICK HERE TO FIND OUT.

Lee Celano / AP Photo

Gerald M. Levin

Lesson: Don’t believe the hype

Gerald Levin masterminded one of history’s most ill-fated deals, merging his company, Time Warner, which controlled some of the best brands and businesses in media, with AOL, which dominated the then-hot business of paid email and Internet access. It was the equivalent of trading gold for a bag of beans, revealed less than a year later when the dot-com bubble burst. Nearly a decade later, Levin’s gaffe has finally been reversed—AOL was spun off December 9, but not after tens of billions of dollars in lost shareholder value.

AP Photo

Robert “Joe” Halderman

Lesson: Love and work don’t mix

Joe Halderman, a CBS News producer who was burdened by debt and hurt by a recent breakup, allegedly decided to blackmail the man with whom his former girlfriend had been sleeping. The problem: the other man was CBS cash cow David Letterman, the asking price was $2 million, and the plot backfired. Letterman admitted all transgressions on television, boosting ratings, and Halderman was arrested and charged with first-degree grand larceny in October. CBS suspended him without pay, ruling that his actions violated a contractual morals clause. He pleaded not guilty to the charge in November.

Gary Malerba / AP Photo

Robert Nardelli

Lesson: Greed is bad

Nardelli became known in business circles as a possible successor to Jack Welch at GE. When that didn’t happen, he was anointed chief executive of Home Depot in December 2000. Under Nardelli, expansion slowed, the company became involved in a backdating investigation (though Nardelli was absolved of fault), and the share price remained stagnant, though revenue and profits grew. But it was his refusal in 2006 to have his pay, which included a $3 million guaranteed annual bonus, tied to the company’s stock performance that instigated his resignation in January 2007. He then became CEO of Chrysler—that run ended this year when the auto maker filed for Chapter 11. Fun.

Louis Lanzano / AP Photo

Dennis Kozlowski

Lesson: Greed is really, really bad

Executive extravagance reached new heights with Dennis Kozlowski, the former CEO of Tyco International who spent $1 million of shareholder funds for his wife’s 40th-birthday bash on Sardinia, complete with a Jimmy Buffett performance and a Statue of David-shaped ice sculpture that urinated vodka. Kozlowski was also given a $19 million loan (that was later forgiven) for a Florida home, as well as $13 million to cover the associated income taxes. In total, Kozlowski was given $135 million from Tyco over five years in loans, charitable donations, and personal expenses. The day before New York City’s district attorney charged him with evading sales tax on art purchases in 2002, Kozlowski stepped down from his post at Tyco. Three years later, he was convicted on 22 counts of grand larceny and securities fraud and sentenced to at least 8.5 years in prison and fined $70 million

Mario Tama / Getty Images

Kenneth D. Lewis

Lesson: Trees don’t grow to the sky

As CEO of Bank of America, Ken Lewis was a Wall Street whiz with a knack for acquiring competitors like FleetBoston and MBNA. Then he botched the biggest deal of his career, as his $50 billion purchase of Merrill Lynch in September 2008 sunk the nation’s largest commercial bank into the heart of the subprime-mortgage sewer. Even a $45 billion government lifeline couldn’t save Lewis’ job. "My decision and the board's to go ahead with the merger was not about a selfish desire to keep our jobs," he said at the time. "Every member of this board, including me, would be all right if we had to leave the company." Lewis announced his “retirement” five months later.

Pat Sullivan / AP Photo; David J. Phillip / AP Photo

Ken Lay / Jeff Skilling

Lesson: Fuzzy math doesn’t add up

In one of the largest bankruptcy filings in American business, Enron went from a $100 billion company in 2000 to the corporate poster child for fraud and scandal. Ken Lay and Jeff Skilling, the chairman and CEO, respectively, at the time of the bankruptcy, had led the Houston energy company to Wall Street success. It later turned out that their success came by using illegal accounting practices to keep losses and debts off its balance sheet. The aftermath included the dissolution of accounting firm Arthur Andersen. Skilling and Lay were found guilty in 2006 on 29 criminal counts, including securities fraud and conspiracy. “Certainly this is not the outcome we expected,” Lay said. “I firmly believe I am innocent of the charges against me, as I have said from Day One.” Then he died.