12 Shadiest CEOs In American History

Source: Klik

CEOs are meant to lead their companies to greener pastures. These CEOs took the reigns at their peaks and ruined their businesses or caused irreparable damage that the companies were never able to recover.


12. Jonathan Schwartz – Sun Microsystems

Jonathan Schwartz

Source: Flickr / JD Lasica

After Jonathan Schwartz had run Sun Microsystems to the ground, the only way the company could survive was through acquisition.

When Schwartz became CEO in April 2006, Sun Microsystems started falling apart, losing its market share to HP and IBM. The shares went from $27 to less than $4. This caused the company to lay off 18% of its employees kicking out more than 6,000 people. In a last ditch effort, the company was forced to survive through acquisition.


11. Ken Lay – Enron

Ken Lay

Source: LoLWot

Made Enron the most successful company through securities fraud then croaked.

Enron’s peak reached $101 billion in sales back in 2000 through several acquisitions and expansions into new businesses. Ken Lay was the CEO from 1986 and quickly helped the company grow through diversification. It was named Fortune’s Most Innovative Company for six years in a row (1996-2001). Most of its liabilities were kept off its balance sheets, and the assets and earnings were doctored. The company eventually filed for bankruptcy with Ken Lay at the heart of the company’s ruins. He was found guilty of securities fraud and passed July 5, 2006, right after being sentenced.


10. Chuck Conaway – K-Mart


Source: Daily Finance

K-Mart brought in Conway to fix its problems, but his defrauding and spending company money made it worse.

K-Mart was a preeminent trailer for the United States since 1899 and controlled a significant portion of the “big box” retailer businesses in all of North America and Australia. By 2000, the company invested in Waldenbooks, Sports Authority, Office Max, and was making a string of failures one after the other. Chuck Conway was brought in to help turn the company around. He said he would improve the company’s supply chain and assist in strengthening its brand to compete with Walmart. In only two years he was charged with defrauding stockholders and accused of spending the company’s money on airplanes and houses.


9. George Shaheen – WebVan.com

George Shaheen

Source: Mouth London

Webvan.com later renamed Accenture tried to make internet grocery shopping a thing.

This company had high hopes of spreading to 26 different cities but could barely manage 10. It spent $1.5 billion and at one point went from 4,500 employees to 2,000 after declaring Chapter 11 bankruptcy. Shaheen failed to get the company up and running without burning through money, and all the retailers were operating on tiny margins that it couldn’t recover from. He made no attempt to work with the board of directors or management to change the operations, and that led to its downfall.


8. Tommy Sopwith – Sopwith Aviation Company

Tommy Sopwith

Source: New Ham Recorder

The CEO of Sopwith Aviation Company couldn’t keep up with the change of time.

The founder of The Sopwith Aviation Company in 1912, was one of the largest aircraft manufacturers in the early 20th century. After the war had ended and couldn’t adapt his products to the commercial market and appeal to the civilian world. He bought ABC Motors Limited in 1919 to try to diversify, but it was already too late for the business. Shortly after, he was charged and punished by anti-profiteering taxes for making exorbitant earnings during the war.


7. John Sculley – Apple

John Sculley

Source: CNBC

The man who fired Steve Jobs.

The board placed Sculley as their CEO based on his business experience with PepsiCo and hoped he could replicate the success at Apple. Seeing Steve Jobs as a threat, he convinced the board to kick his rival to the curb. He lacked the technical background and invested in several failed ventures. Because he had no knowledge of the technical details of the products the company was creating and he was removed. In 1997, Apple absorbed the company Jobs had created and made him CEO that same year.


6. Bernard Ebbers – WorldCom

Bernard Ebbers

Source: Fortune

When your CEO is imprisoned for fraud and conspiracy you know you have a bad boss.

Ebbers was a CEO of Worldcom’s predecessor firms in 1985. He helped the company grow through acquisitions and made Worldcom the second largest long distance company in the United States. In 1999, he tried to buy Sprint but his deal was picked apart by regulators, and it eventually fell through. On top of his big flop, he was selling portions of his stock to maintain his lavished lifestyle. Internal auditors discovered that Ebbers was also committing a financial fraud of $3.8 billion in 2002. Worldcom filed for Chapter 11 bankruptcy. Ebbers was convicted of fraud, conspiracy and for filing false documents. He was sentenced to 25 years.


5. Angelo Mozilo – CountryWide

Angelo Mozilo

Source: Business Insider

While Countrywide was going up in flames, Mozilo was raking in the money.

The co-founder of Countrywide Credit Industries, Angelo Mozilo made a system of laying off risk by reselling bundled loans as mortgage-backed securities. They expanded their services to be able to make loans, service loans through collections and handle closings with real estate appraisal services. They had grown so large that by the mid-2000s they had issued over 15% of all home loans in the United States. When the housing bubble crashed, so did Countrywide. In the middle of all of this Mozilo was selling his shares of the company to make over $300 million.


4. John Rigas – Adelphia Communications

John Rigas

Source: Biography

You can blame Adelphia Communications for bad service on Time Warner Cable.

Founded in 1952, Adelphia Communications was one of the largest cable and internet companies in the United States they had over 5 million subscribers and were in over 30 states. The company filed for bankruptcy in 2002 because Rigas was siphoned off over $100 million to fund other businesses owned by his family. He was charged and sentenced. Adelphia assets were purchased by Time Warner Cable.


3. Juergen Schrempp – DaimlerChrysler

Juergen Schrempp

Source: Motor Talk

Merged two big companies and didn’t know what to do with them.

Juergen Schrempp was the one who orchestrated the merger between Daimler and Chrysler. He sold the merger to shareholders as a way for Chrysler to reap the benefits of parts and technology from Daimler. After the merger, the Chrysler executives were resistant to his plans. A year after, Chrysler’s marketing and manufacturing operations started crumbling and in only a year lost over 50% of its market cap. Schrempp was quickly kicked out by his board in 2005 and Chrysler was bought by Cerberus Capital Management for $7.4 billion in 2007.


2. Kay R. Whitmore – Kodak


Source: Democratic Chronicle

Eastman Kodak was the front-runner and inventor of its own demise.

Kodak was founded in 1880 and was considered the gold standard for the film and camera industries. It thrives through most of the 1900s until Kay R. Whitmore took control. By jacking up the prices, he hoped that the brand would win out over its price, which it didn’t. Even though Kodak was the first to invent a the digital camera and the first mega-pixel camera, it was too slow to keep up with the digital world thinking that film would win out in the end, but film and film paper became a dying art.


1. Eckhard Pfeiffer – Compaq

Eckhard Pfeiffer

Source: Quotation Of


Compaq was the first to create a portable computer that would revolutionize the technology for PCs and laptops. When Pfeiffer took over as CEO in 1991, he started purchasing companies like Tandem, DEC which would eventually become obsolete. What he didn’t know what that he could have used the assets from DEC like Altavista, which was the original search engine and predecessor for Google and Yahoo! By taking the company up-market, competitors like Dell and Gateway went for lower priced and blew Compaq out of the water.