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​As we've seen with the recent controversy over Los Angeles Clippers owner Donald Sterling, the worst company heads can be crude and shockingly unenlightened. It takes a special kind of poisonous talent, though, for a boss to engage in actions that wipe out the value of their company.

Luckily for the stock market and individual shareholders, the Clippers are not a publicly traded entity. Some other once-big-name firms, however, aren't so fortunate. Here's a look at several of the more egregious recent examples of destructive CEO behavior.

Kenneth Lay, Enron

Now a byword for corporate fraud on a massive scale, Enron was an energy conglomerate that posted impressive results throughout the 1990s, at one point reporting over $100 billion in revenues.

Such numbers sounded too good to be true, and they were. Lay and company did this through widespread and pervasive fraud using a variety of dirty accounting tricks. Lay was found guilty of 10 counts of securities fraud and related charges in 2006, but he died several months before he was scheduled to be sentenced.

While it was a stock market darling, Enron stock hit nearly $91 per share at one point. Barely a year and a half later, after the scandal broke, it could be had for a mere 12 cents.

Bernie Ebbers, WorldCom

With large-scale deregulation recently behind it and the rise of the Internet ahead, the telecom industry was exciting in the 1990s. And few companies were as thrilling to watch as hungry operator WorldCom.

The busy company grew huge through acquisitions, swallowing companies such as CompuServe and MCI Communications, and reaching an ultimately unconsummated deal to merge with Sprint (S).

But a general corporate pullback on telecom spending started to bite, the debts piled up, and the company's stock began to slide. In desperation, management started to cook the books in order to inflate net profit.

The company was forced to enter Chapter 11, and ultimately Ebbers was socked with a raft of charges, including fraud and conspiracy, for which he was sentenced to 25 years in jail in 2005.

Shareholders were left holding the phone. WorldCom stock was canceled outright, becoming completely worthless. In 2005, Verizon (VZ) bought its successor company for $7.65 billion.

L. Dennis Kozlowski, Tyco

When your company funds a lavish, $2 million party nicknamed "the Roman Orgy," claiming that it's a shareholder meeting, you know you're in trouble. This was only one of the many hallmarks of Dennis Kozlowski's tenure as CEO of sprawling conglomerate Tyco International (TYC).

That lavish soiree was indicative of his style as a boss: Kozlowski was a guy who liked to spend. Tyco under his reign was an insatiable acquirer, buying everything from pharmaceutical companies to sprinkler manufacturers.

The problem was he didn't seem to distinguish between acquiring assets for the company and adding to his personal stash. The law soon caught up with Kozlowski, and in 2005 he and Tyco's ex-CFO Mark Swartz were found guilty of 22 counts of conspiracy, grand larceny and securities fraud. The onetime CEO served time until earlier this year, when he was released on parole.

Tyco shares trade at around $40 a share these days, far from the onetime high of over $120.

John Rigas (and sons), Adelphia Communications

It's bad enough when a single individual wrecks his or her company through greed and mismanagement. It's much worse if their family joins in on the looting.

Cable powerhouse Adelphia Communications was led by CEO John Rigas, whose sons Timothy as chief financial officer and Michael as executive vice president of operations.

In 2002, Adelphia disclosed that the Rigases "co-borrowed" $2.3 billion with the company. Among other misdeeds, they were accused of tapping more than $250 million in corporate funds to meet margin calls on their personal investments,and spending nearly $13 million to build a golf course.

John received a 15-year sentence for fraud and conspiracy. Timothy was hit with a tougher stretch of 20 years. Michael walked away relatively unscathed with a 10-month home-confinement sentence.

In 2006, Comcast (CMCSA) and Time Warner Cable (TWC) carved up the useful assets of the firm, acquiring them for a combined $17.6 billion. Adelphia technically still exists today, but it's essentially a paper entity and a hollow shell of the big company it once was.

Motley Fool contributor Eric Volkman has no position in any stocks mentioned. Nor does The Motley Fool.

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CP Rail stock is wildly overinflated based on Hunter Harrison's lies. Investors beware your money is not safe and the company's performance is based on smoke and mirrors. The collapse is coming soon.

December 06 2014 at 12:52 PM Report abuse rate up rate down Reply

Don't forget Hunter Harrison for his union busting book cooking tactics. The man feels that the only good employee is a fired employee.

December 06 2014 at 12:49 PM Report abuse rate up rate down Reply

Billionaires' Tea Party, The
How Corporate America is Faking a Grassroots Revolution

Shortly after Barack Obama and a Congressional Democrats swept to power promising a new era of hope and change, a citizens protest movement emerged threatening to derail their agenda. The Tea Party was widely hailed as a exercise in grassroots democracy. But others saw it as a classic example of "astroturfing," a public relations charade designed to mimic a populist revolt. Curious to find out for himself, Australian filmmaker Taki Oldham decided to travel into the heart of the movement. The result is this astonishing look at how moneyed elites have been exploiting legitimate voter outrage to advance their own narrow interests. Oldham takes us inside town hall meetings where angry voters parrot insurance industry PR; finds "citizen groups" working to debunk climate change that are funded by big oil companies; and peels back a movement's down-home image to discover a coordinated network of right-wing shadow groups funded by the likes of billionaire ideologue Charles and David Koch. At once a record of our political moment, and a stunning case study in the power of public relations.

(Previously known as AstroTurf Wars.)

Filmmaker Info
Camera, Director, Editor, Producer: Taki Oldham
Voiceover Recording Engineer: Davide Carbone
Additional Editing: Bergen O'Brian
Additional Graphics: Daniel Nicholas

Press Reviews
Vermont Commons

Praise for the Film
"Taki Oldham's documentary is journalism at its best. I wish every American could see it before the election. I just watched it and am even more concerned about the future of our democracy than ever before."
- Wendell Potter | Author of Deadly Spin: An Insurance Industry Insider Speaks Out on How Corporate PR is Killing Health Care and Deceiving Americans

May 10 2014 at 1:14 AM Report abuse rate up rate down Reply

These Liberal CEO's are something else.

May 09 2014 at 11:48 AM Report abuse -3 rate up rate down Reply
1 reply to alfrankenfool's comment

And you little flying koch monkeys flitting in here screeching and shrieking for your nickel a post are the same ol' same ol' boooooooring. Now go flitting back to your koch masters, little flying koch monkey, screeching and shrieking all the way and as you kneel before them tell them we do not need you here. Now BEGONE, little flying koch monkey, BEGONE!!

May 09 2014 at 12:07 PM Report abuse +1 rate up rate down Reply
1 reply to hsenpfeffer's comment

Ahhh yess the little flying koch monkey back with ANOTHER of her many screen names. Now go back to kneeling before your koch masters little koch monkey. No one needs you here.

May 09 2014 at 4:43 PM Report abuse +4 rate up rate down

Barack Obama. Harry Reid. Nancy Pelosi. Timmy "Tax Cheat" Geithner.

May 09 2014 at 11:31 AM Report abuse -3 rate up rate down Reply
1 reply to jdykbpl45's comment

You forgot moderate Mitt Romney who refused to show 10 years of tax returns in the 2012 elections.

May 09 2014 at 4:51 PM Report abuse +2 rate up rate down Reply
2 replies to republicanslostagain's comment

Bengazi anyone?

May 09 2014 at 9:19 PM Report abuse -1 rate up rate down

Bush's war crimes.

May 10 2014 at 1:07 AM Report abuse +1 rate up rate down

Ah.....our daily hate business article on AOL. Try again, these guys were news years ago.

May 09 2014 at 10:05 AM Report abuse rate up rate down Reply
1 reply to chuckhalper's comment

The businessboys make themselves easy to hate. Ever since the takeover of legitimate business by salestrash and finance scammers under the regime of the first worthless salesboy president, ronnie reagan, business in America has few redeeming qualities. It is entirely focused an scamming, skimming, price inflation and gouging and totally without concern for productivity, quality or integrity. Till we throw out 90 percent of the salestrash, marketeering trash and their salestrash parasite non values our businesses and economy will not heal.

May 09 2014 at 11:07 AM Report abuse +1 rate up rate down Reply
1 reply to hsenpfeffer's comment

Now little flying koch monkey go shrieking and screeching back to your koch masters and tell them we do not need you here no matter how many screen names you post under, whether it is truliberal1 or any of the other names you use for your nickel a post nonsense. Now go back to kneeling before your koch masters but tell them we do not need you or any of their nonsense. Now BEGONE little flying koch monkey, BEGONE!!

May 09 2014 at 12:10 PM Report abuse +1 rate up rate down

Today's Banking & Wall Street CEO's don't seem to have to worry. Our criminal system appears to have placed them above any laws.

It's time to replace those in charge of our justice system,. They are only aiding and abetting what may be the the biggets crimnals of all times.

May 09 2014 at 7:46 AM Report abuse rate up rate down Reply