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Portfolio's Worst American CEOs of All Time

The Worst American CEOs of All Time
Throughout the history of business, the failure or success of a company has relied on many factors, not the least of which is the corporate savvy or managerial shortcomings of the executive at the top. Recently, many CEOs have come under fire for mismanagement, costing taxpayer and shareholder money alike amid the worst economic downturn in decades. So how do these corporate leaders stack up against the worst CEOs of all time? To answer that question, assembled a panel of professors from top bu

Throughout the history of business, the failure or success of a company has relied on many factors, not the least of which is the corporate savvy or managerial shortcomings of the executive at the top. Recently, many CEOs have come under fire for mismanagement, costing taxpayer and shareholder money alike amid the worst economic downturn in decades.

So how do these corporate leaders stack up against the worst CEOs of all time? To answer that question, Portfolio.com assembled a panel of professors from top business schools, surveying them on records of CEOs who most effectively destroyed value and innovation while displaying the worst management skills throughout their management tenure. Here is the result of their findings: The 20 Worst American CEOs of all time.

Rankings By: Portfolio.com
Posted 30 Apr 2009

20. Vikram Pandit
Pandit didn’t create the mess Citi is in, but he is the financial services equivalent of the Titanic’s Edward Smith—a commander ill-equipped to save his ship. When Pandit took over, Citi was already on track to report write-downs and increased credit costs of $20 billion. Today, the banking supermarket is propped up by $45 billion in bailouts and is, in effect, owned by the U.S. government.THE STAT: Although Pandit’s currently earning $1 a year, his pay package was valued at $38.2 million for 20
By Portfolio.com

Pandit didn’t create the mess Citi is in, but he is the financial services equivalent of the Titanic’s Edward Smith—a commander ill-equipped to save his ship. When Pandit took over, Citi was already on track to report write-downs and increased credit costs of $20 billion. Today, the banking supermarket is propped up by $45 billion in bailouts and is, in effect, owned by the U.S. government.

THE STAT: Although Pandit’s currently earning $1 a year, his pay package was valued at $38.2 million for 2008, a year when taxpayers kept the firm in business.
Citigroup's Company Website

19. Carly Fiorina
A consummate self-promoter, Fiorina was busy pontificating on the lecture circuit and posing for magazine covers while her company floundered. She paid herself handsome bonuses and perks while laying off thousands of employees to cut costs. The merger Fiorina orchestrated with Compaq in 2002 was widely seen as a failure. She was ousted in 2005.THE STAT: HP stock lost half its value during Fiorina’s tenure.
By Portfolio.com

A consummate self-promoter, Fiorina was busy pontificating on the lecture circuit and posing for magazine covers while her company floundered. She paid herself handsome bonuses and perks while laying off thousands of employees to cut costs. The merger Fiorina orchestrated with Compaq in 2002 was widely seen as a failure. She was ousted in 2005.

THE STAT: HP stock lost half its value during Fiorina’s tenure.

HP's Company Website

18. Stan O’Neal
O’Neal’s abrasive personality and ruthless cost cutting earned him many enemies, but his push toward riskier bets and subprime exposure led to his ouster. After Merrill posted the biggest quarterly loss in its 93-year history—and O’Neal was caught approaching Wachovia about a merger without the board’s approval—he was finally fired.THE STAT: O’Neal walked out the door with $161.5 million in severance.
By Portfolio.com

O’Neal’s abrasive personality and ruthless cost cutting earned him many enemies, but his push toward riskier bets and subprime exposure led to his ouster. After Merrill posted the biggest quarterly loss in its 93-year history—and O’Neal was caught approaching Wachovia about a merger without the board’s approval—he was finally fired.

THE STAT: O’Neal walked out the door with $161.5 million in severance.

Merrill Lynch Company Website

17. Bob Nardelli
Nardelli was fired from Home Depot after losing market share, alienating executives, downplaying customer service, and refusing to cut his fat pay package. He was then hired by the private equity group Cerberus, which put him in charge of its struggling Chrysler unit. There, he took billions in government aid, only to face an ultimatum: Merge or face certain liquidation.THE STAT: Nardelli’s Home Depot exit package of $210 million was regarded as one of the largest ever.
By Portfolio.com

Nardelli was fired from Home Depot after losing market share, alienating executives, downplaying customer service, and refusing to cut his fat pay package. He was then hired by the private equity group Cerberus, which put him in charge of its struggling Chrysler unit. There, he took billions in government aid, only to face an ultimatum: Merge or face certain liquidation.

THE STAT: Nardelli’s Home Depot exit package of $210 million was regarded as one of the largest ever.

Chrysler Company Website

16. Gerald Levin
Levin’s failure comes down to one colossal mistake: In his desperate eagerness to become a new-media CEO, he orchestrated a megamerger between Time Warner and a vastly overvalued AOL—one of the worst acquisition deals ever. “He had the largest midlife crisis in the history of American capitalism,” one of our panelists quipped.THE STAT: The AOL deal destroyed over $200 billion in Time Warner shareholder value.
By Portfolio.com

Levin’s failure comes down to one colossal mistake: In his desperate eagerness to become a new-media CEO, he orchestrated a megamerger between Time Warner and a vastly overvalued AOL—one of the worst acquisition deals ever. “He had the largest midlife crisis in the history of American capitalism,” one of our panelists quipped.

THE STAT: The AOL deal destroyed over $200 billion in Time Warner shareholder value.

Time Warner Company Website

15. Martin Sullivan
Get out your tomatoes. This is the guy who approved those “retention” bonuses that AIG tried to pay after sucking up nearly $200 billion from U.S. taxpayers. Sullivan was ousted before the bailout, but his inaction as CEO helped create AIG’s mess. He brushed off the firm’s subprime exposure as “manageable” while writedowns mounted and the firm recorded its two largest-ever quarterly losses.THE STAT: Sullivan’s severance package was $25.4 million, including $322,000 for private use of corporate a
By Portfolio.com

Get out your tomatoes. This is the guy who approved those “retention” bonuses that AIG tried to pay after sucking up nearly $200 billion from U.S. taxpayers. Sullivan was ousted before the bailout, but his inaction as CEO helped create AIG’s mess. He brushed off the firm’s subprime exposure as “manageable” while writedowns mounted and the firm recorded its two largest-ever quarterly losses.

THE STAT: Sullivan’s severance package was $25.4 million, including $322,000 for private use of corporate aircraft.

AIG Company Website

14. John Sculley
Sculley forced Steve Jobs out of Apple. Enough said. But let’s continue: Though he was a brilliant marketer at Pepsi, he proved to be disastrous as the top manager of a tech company and unsophisticated about the technology field. His tenure was marred by infighting among top managers and expensive projects that flopped in the marketplace. (Remember the Apple Newton?) Sculley boosted the price of the Macintosh when personal computer prices were falling. The board ousted him in 1993, when Apple wa
By Portfolio.com

Sculley forced Steve Jobs out of Apple. Enough said. But let’s continue: Though he was a brilliant marketer at Pepsi, he proved to be disastrous as the top manager of a tech company and unsophisticated about the technology field. His tenure was marred by infighting among top managers and expensive projects that flopped in the marketplace. (Remember the Apple Newton?) Sculley boosted the price of the Macintosh when personal computer prices were falling. The board ousted him in 1993, when Apple was slipping toward bankruptcy.

THE STAT: In 1987, Sculley was ­reported to be the highest-paid executive in Silicon Valley, earning a then-unheard-of $2.2 million.

Apple Company Website

13. Roger Smith
The CEO’s job is often thankless, and no one was ever thanked less than Roger Smith, General Motors chairman from 1981 to 1990 and the unwitting stooge of Michael Moore’s mockumentary Roger and Me. He started his career at the company in 1949 as a green-eyeshade guy, a lowly accounting clerk. His 1984 reorganization attempted to streamline GM’s back-of-the-house operations but was, in a word, a disaster. It sowed confusion and disorder that practically idled the automaker for months. Current CEO
By Portfolio.com

The CEO’s job is often thankless, and no one was ever thanked less than Roger Smith, General Motors chairman from 1981 to 1990 and the unwitting stooge of Michael Moore’s mockumentary Roger and Me.

He started his career at the company in 1949 as a green-eyeshade guy, a lowly accounting clerk. His 1984 reorganization attempted to streamline GM’s back-of-the-house operations but was, in a word, a disaster. It sowed confusion and disorder that practically idled the automaker for months. Current CEO Rick ­Wagoner has said, “We’ve been 12 to 14 years digging out from that.”

Smith, a tightly wound, work-all-night autocrat, remote and austere, had the right idea but may have lacked the intuition to understand how his rip-up-the-carpet redo would affect the delicate web of informal communication that GM relied upon. Few today would dispute that GM had to consolidate the sprawling conglomerate Alfred Sloan took control of in the 1920s. If only Smith had done the job more artfully.

General Motors Company Website

12. Bob Allen
Bob Allen misjudged where the telecom industry was going. He forced a disastrous merger with computer company NCR Corp. and allowed AT&T to wither under his lack of strategic direction. In 1997, after AT&T lost more than $12 billion in a few months, Time called the company a “monolithic screwup.”THE STAT: To stem the company’s losses on his watch, Allen had to lay off 50,000 AT&T employees.
By Portfolio.com

Bob Allen misjudged where the telecom industry was going. He forced a disastrous merger with computer company NCR Corp. and allowed AT&T to wither under his lack of strategic direction. In 1997, after AT&T lost more than $12 billion in a few months, Time called the company a “monolithic screwup.”

THE STAT: To stem the company’s losses on his watch, Allen had to lay off 50,000 AT&T employees.

AT&T Company Website

11. Henry Frick
A father of the modern steel industry (along with his business partner, Andrew Carnegie), Frick was a vicious anti-unionist who was once voted the most hated man in America. His response to a strike at one of his steel mills—which began after he attempted to lower wages—resulted in 16 deaths and is regarded as one of the most notorious incidents in U.S. labor history. Afterward, he was shot three times and stabbed twice by an irate activist. He survived and made a full recovery. THE STAT: Under
By Portfolio.com

A father of the modern steel industry (along with his business partner, Andrew Carnegie), Frick was a vicious anti-unionist who was once voted the most hated man in America. His response to a strike at one of his steel mills—which began after he attempted to lower wages—resulted in 16 deaths and is regarded as one of the most notorious incidents in U.S. labor history. Afterward, he was shot three times and stabbed twice by an irate activist. He survived and made a full recovery.

THE STAT: Under Frick, Carnegie Steel became the largest steel company in the world, valued at $25 million.

10. John Akers
While the rest of the world was moving toward personal computing, ­Akers remained stuck in the mainframe age, never quite figuring out what to do with IBM at a critical point in the tech industry’s evolution. Many outsiders viewed Akers as being in over his head. IBM was paralyzed by his lack of decisiveness. THE STAT: Akers stepped down shortly after the company announced a $4.97 billion net loss for 1992.
By Portfolio.com

While the rest of the world was moving toward personal computing, ­Akers remained stuck in the mainframe age, never quite figuring out what to do with IBM at a critical point in the tech industry’s evolution. Many outsiders viewed Akers as being in over his head. IBM was paralyzed by his lack of decisiveness.

THE STAT: Akers stepped down shortly after the company announced a $4.97 billion net loss for 1992.

IBM Company Website

9. John Patterson
The tyrannical Patterson liked to fire and then rehire executives to break their self-esteem. He banned “harmful” foods—including bread and butter—from company premises and had employees weighed and measured every six months. In 1913, he and 29 NCR officials were convicted of various antitrust violations, including the use of “knockout men” to intimidate store owners and keep them from buying from NCR’s competitors. (The conviction was overturned a year later.) Patterson may be best known for fi
By Portfolio.com

The tyrannical Patterson liked to fire and then rehire executives to break their self-esteem. He banned “harmful” foods—including bread and butter—from company premises and had employees weighed and measured every six months. In 1913, he and 29 NCR officials were convicted of various antitrust violations, including the use of “knockout men” to intimidate store owners and keep them from buying from NCR’s competitors. (The conviction was overturned a year later.) Patterson may be best known for firing Thomas Watson, who went on to build IBM.

THE STAT: Today, NCR is worth $1.5 billion.

8. Jay Gould
When it comes to unscrupulous behavior, Gould makes Milken look like a sweetheart. A railroad developer and speculator, Gould sold out his associates, bribed legislators to get deals done, and even kidnapped a potential investor. He duped the U.S. Treasury, pushing up the price of gold and prompting a scare on Wall Street that depressed all stocks. After hiring strikebreakers during a railroad strike in 1886, he was reported to have said, “I can hire one half of the working class to kill the oth
By Portfolio.com

When it comes to unscrupulous behavior, Gould makes Milken look like a sweetheart. A railroad developer and speculator, Gould sold out his associates, bribed legislators to get deals done, and even kidnapped a potential investor. He duped the U.S. Treasury, pushing up the price of gold and prompting a scare on Wall Street that depressed all stocks. After hiring strikebreakers during a railroad strike in 1886, he was reported to have said, “I can hire one half of the working class to kill the other half.”

THE STAT: When Gould died, his fortune was worth an estimated $67 billion in inflation-adjusted dollars.

7. Fred Joseph
As Michael Milken’s boss, Joseph led Drexel to “it” firm status on Wall Street in the 1980s. He then oversaw its plunge into bankruptcy in 1990, after company executives were convicted of insider trading and forced to pay $650 million in fines. There was no evidence that Joseph himself committed a crime, but his poor management left the company without a crisis plan. In 1992, Drexel defaulted on $100 million in loans and closed up shop. Unlike Milken, Joseph didn’t go to jail, but he was banishe
By Portfolio.com

As Michael Milken’s boss, Joseph led Drexel to “it” firm status on Wall Street in the 1980s. He then oversaw its plunge into bankruptcy in 1990, after company executives were convicted of insider trading and forced to pay $650 million in fines. There was no evidence that Joseph himself committed a crime, but his poor management left the company without a crisis plan. In 1992, Drexel defaulted on $100 million in loans and closed up shop. Unlike Milken, Joseph didn’t go to jail, but he was banished from being a Wall Street CEO for life.

THE STAT: Joseph has since become managing director of Morgan Joseph & Co. In 2007, an industry group named him investment banker of the year.

6. Al Dunlap
Picked by the board of Scott Paper Co. as the man to turn the struggling company around, Dunlap earned his nickname “Chainsaw Al” by ­slicing 11,000 employees. When Scott merged with Kimberly-Clark, Dunlap’s payoff was estimated at more than $100 million.Dunlap’s memoir/manifesto, Mean Business, roughly coincided with his next CEO star turn, which was also to be his last. Sunbeam’s stock surged on the news that the Chainsaw was coming; massive workforce reductions and factory closures followed w
By Portfolio.com

Picked by the board of Scott Paper Co. as the man to turn the struggling company around, Dunlap earned his nickname “Chainsaw Al” by ­slicing 11,000 employees. When Scott merged with Kimberly-Clark, Dunlap’s payoff was estimated at more than $100 million.

Dunlap’s memoir/manifesto, Mean Business, roughly coincided with his next CEO star turn, which was also to be his last. Sunbeam’s stock surged on the news that the Chainsaw was coming; massive workforce reductions and factory closures followed within months. His book clearly explained what set him apart from “addle-brained” and “weak” executives: “I’m a superstar in my field,” he wrote.

Could there be a clearer sell signal? Unable to flip Sunbeam to a new buyer, as he’d done with Scott, Dunlap was stuck actually running the company. He failed spectacularly. Within two miserable years, the board fired him. The tactics he’d used to stave off losses—the company overstated its net income by $60 million, which was real money back then—earned him a civil suit from the SEC and a class-action suit by shareholders. Dunlap eventually settled both and was barred from serving as an officer or director of any public company. You could call Chainsaw Al’s story a fall from grace, but in his case, that’s probably not the proper word.

5. Bernie Ebbers
The ultimate corporate shopaholic, Ebbers bought an obscure telephone carrier in the 1980s and went on a 17-year acquisition binge that turned it into the world’s largest telecom company. Alas, his passion for deal­making didn’t translate into the savvy necessary for running the complex business. When telecom stocks went south in 2000, the company’s massive debt was exposed. Ebbers tried to disguise it through fraudulent accounting. In 2005, three years after WorldCom filed for bankruptcy, he wa
By Portfolio.com

The ultimate corporate shopaholic, Ebbers bought an obscure telephone carrier in the 1980s and went on a 17-year acquisition binge that turned it into the world’s largest telecom company. Alas, his passion for deal­making didn’t translate into the savvy necessary for running the complex business. When telecom stocks went south in 2000, the company’s massive debt was exposed. Ebbers tried to disguise it through fraudulent accounting. In 2005, three years after WorldCom filed for bankruptcy, he was convicted of overseeing $11 billion worth of accounting fraud. He’s now serving a 25-year prison term.

THE STAT: When Ebbers resigned, in 2002, WorldCom stock had fallen to $1.79 from a peak of $64.50 in 1999.

Enron Creditors Recovery Corp.

4. Jimmy Cayne
Talk about an out-of-touch leader. Cayne was playing bridge when two Bear Stearns hedge funds collapsed in July 2007, and was again the following March when a liquidity crisis at the firm led to its emergency sale to J.P. Morgan. Never mind that its share price was $10 (less than 3 percent of its high of $170); Cayne will spend the rest of his days living down reports that one of his other favorite pursuits was smoking pot. THE STAT: What a difference a year makes: A share price of $10 doesn’t s
By Portfolio.com

Talk about an out-of-touch leader. Cayne was playing bridge when two Bear Stearns hedge funds collapsed in July 2007, and was again the following March when a liquidity crisis at the firm led to its emergency sale to J.P. Morgan. Never mind that its share price was $10 (less than 3 percent of its high of $170); Cayne will spend the rest of his days living down reports that one of his other favorite pursuits was smoking pot.

THE STAT: What a difference a year makes: A share price of $10 doesn’t sound too bad these days.

Bear Stearns Company Website

3. Ken Lay
When it comes to bad CEOs, Lay was the complete package: He was not only dishonest but disastrously inept as a manager as well. Lay, who founded Enron and turned it into a $70 billion energy company, was uninterested in the day-to-day tasks of running the business. Consequently, he gave free rein to untrustworthy subordinates like Jeff Skilling and Andy Fastow. He also signed off on a maze of convoluted transactions that formed the basis of a massive accounting fraud that would wipe out investor
By Portfolio.com

When it comes to bad CEOs, Lay was the complete package: He was not only dishonest but disastrously inept as a manager as well. Lay, who founded Enron and turned it into a $70 billion energy company, was uninterested in the day-to-day tasks of running the business.

Consequently, he gave free rein to untrustworthy subordinates like Jeff Skilling and Andy Fastow. He also signed off on a maze of convoluted transactions that formed the basis of a massive accounting fraud that would wipe out investors and bring down the corporation. Lay was convicted of securities fraud in 2006. If he hadn’t died soon afterward, he would have faced as many as 30 years in prison.

THE STAT: Enron stock lost 99.7 percent of its value in 2001.

Enron Creditors Recovery Corp.

2. Angelo Mozilo
Meet the man who made subprime a household word. Once a symbol of self-made accomplishment—a butcher’s son who built the largest mortgage lender in the country—Mozilo became blinded by success and began going after the riskiest and most unsavory of borrowers to boost his company’s market share. In doing so, he legitimized a sector that would ultimately bring down the economy. THE STAT: Mozilo’s once-secret, now-infamous “Friends of Angelo” program provided loans on favorable terms to politically
By Portfolio.com

Meet the man who made subprime a household word. Once a symbol of self-made accomplishment—a butcher’s son who built the largest mortgage lender in the country—Mozilo became blinded by success and began going after the riskiest and most unsavory of borrowers to boost his company’s market share. In doing so, he legitimized a sector that would ultimately bring down the economy.

THE STAT: Mozilo’s once-secret, now-infamous “Friends of Angelo” program provided loans on favorable terms to politically influential borrowers, including Senators Kent Conrad and Chris Dodd.

1. Dick Fuld
It’s one thing to oversee the collapse of one of Wall Street’s most esteemed firms. But when your hubris triggers a national financial panic as well, you’re a shoo-in for top prize. Fuld’s reckless risk-taking may have been typical of Wall Street, but his refusal to acknowledge that his firm was in trouble—and take the steps necessary to save it—was beyond the pale. Since filing the largest bankruptcy in U.S. history ($613 billion in debts outstanding), Fuld has been belligerent and unrepentant.
By Portfolio.com

It’s one thing to oversee the collapse of one of Wall Street’s most esteemed firms, Lehman Brothers. But when your hubris triggers a national financial panic as well, you’re a shoo-in for top prize. Fuld’s reckless risk-taking may have been typical of Wall Street, but his refusal to acknowledge that his firm was in trouble—and take the steps necessary to save it—was beyond the pale. Since filing the largest bankruptcy in U.S. history ($613 billion in debts outstanding), Fuld has been belligerent and unrepentant. Even Bernie Madoff said he was sorry.

THE STAT: Fuld was recently spotted trying to figure out the Jet Blue check-in machines at La Guardia Airport.