Monstrous Managers: 15 of the Most Hated CEOs of All Time

CEOs take a lot of heat. They’re in lofty positions with a lot of power, and typically the buck stops with them. They’re ultimately responsible for anything and everything that happens under their watch, and that sometimes means earning incredible amounts of money or resigning in disgrace.
There are CEOs we all admire. You probably can name several off the top of your head. Bill Gates, Elon Musk, and Warren Buffett all come to mind. Their companies largely have a positive public impact.
But there are also villainous executives — the Darth Vaders of the business world. These men and women seem to put their interests in front of everyone else’s, sewing chaos and harming their employees, the environment, or their shareholders. There’s a long list of those individuals, too. Some of them never intended to play the part of the bad guy. Others went in knowing they’d be branded as public enemies, but at least they’d be rich.
Here are 15 of those villainous and monstrous managers, starting with one who’s quickly become one of America’s most hated people: the dreaded “pharma bro” himself.

15. Martin Shkreli: Turing Pharmaceuticals

Martin Shkreli, former CEO of Turing Pharmaceuticals, smiles while being questioned by a Congressional committee.
Former CEO of Turing Pharmaceuticals Martin Shkreli smiles during questioning by a Congressional committee. | Mark Wilson/Getty Images
  • Martin Shkreli drew criticism for dramatically increasing the price of a popular AIDS medication.

We’ll kick off with a timely addition. Martin Shkreli was CEO of Turing Pharmaceuticals and found himself in trouble after jacking up the price of a popular drug for AIDS patients from $13 to $750 per pill. Naturally, everyone was angry at him, and it culminated with his arrest. He was even chided by President Donald Trump of all people, who called him “disgusting” and “a spoiled brat.”
“Leadership is morally bankrupt,” a former Turing employee wrote on Glassdoor. “25% of company laid off 3 days before Christmas with 2 weeks of severance. … If you see a job opening at Turing, run the opposite direction — fast.”
Next: A media giant worth more than $12 billion

14. Rupert Murdoch: News Corporation

Rupert Murdoch and sons
The Murdoch family, from left, Lachlan, Rupert, and James Murdoch | John Phillips/Getty Images
  • Some of Rupert Murdoch’s media properties promote his right-leaning views.

Media giant Rupert Murdoch has had a wildly successful career. He’s probably best known for being the man behind the rise of Fox News, part of his News Corporation empire. Originally from Australia, he’s amassed a fortune of more than $12 billion as of 2017. He is a villain in the eyes of many because of his hard-right views and politics, which are pushed by some of his media properties.
“The company’s reputation is well deserved,” a former employee wrote on Glassdoor. “Business practices are right on the edge of acceptable and sometimes cross the line. Some units are extremely aggressive in promoting the company’s political viewpoint.”
Next: One of the greatest frauds of all time

13. Ken Lay: Enron

Former Enron chairman Kenneth Lay leaves the courthouse
Former Enron chairman Kenneth Lay leaves the courthouse after the day’s proceedings in his fraud and conspiracy trial. | Dave Einsel/Getty Images
  • Ken Lay was one of the people behind the Enron scandal.

Ken Lay was one of a handful of executives who went down in the Enron scandal. It ultimately left the company bankrupt and thousands of employees without jobs. By hiding losses, Enron’s execs were able to convince investors the company was on the up-and-up, only for it all to come crashing down. Lay was one of the men behind it all, though he ended up dying of a heart attack before he could actually be sentenced for his crimes.
Next: You either love him or hate him (and his products).

12. Steve Jobs: Apple

Apple CEO Steve Jobs holds up an iPhone
Apple CEO Steve Jobs holds up an iPhone. | David Paul Morris/Getty Images
  • Many people thought Steve Jobs was a jerk.

Now here’s a confounding figure. Steve Jobs is one of those people who’s paradoxically loved and despised by millions. A visionary and unrelenting jerk, according to those close to him, Jobs led Apple to the forefront of the tech boom. Jobs has since died, and even Apple fans seem to have a love-hate relationship with him.
“Brow beat to do the job one way in the exhausting training and expected to the opposite on the job,” a former Apple employee wrote on Glassdoor. “Complete lack of respect for anyone who doesn’t use or own an Apple computer. Expected to worship the ground Steve Jobs walks on.”
Next: Another controversial Apple figure

11. John Sculley: Apple

John Sculley speaks onstage at the Kairos Society Global Summit At One World Observatory
Former Apple CEO John Sculley speaks on stage at the Kairos Society Global Summit At One World Observatory. | Brad Barket/Getty Images for Kairos Society
  • John Sculley was blamed for Apple falling behind the times during his tenure.

At one point, Apple’s board relieved Jobs of his CEO duties and gave John Sculley the reins. This is the period during which Apple seemed to regress and fall behind the times. Sculley was blamed for it, as during his 10-year tenure he refocused the company on profitability rather than innovation. Jobs returned in 1993 and turned Apple into the company we know today. Sculley has, however, gone on to be successful in many other areas.
Next: This CEO couldn’t save his retail company.

10. Edward Lampert: Sears Holdings

Alan J. Lacy, vice chairman and CEO of Sears Holdings; Edward S. Lampert, chairman of Sears Holdings; and Aylwin B. Lewis, president of Sears Holdings and CEO of Kmart and Sears Retail
Alan J. Lacy, vice chairman and CEO of Sears Holdings; Edward S. Lampert, chairman of Sears Holdings; and Aylwin B. Lewis, president of Sears Holdings and CEO of Kmart and Sears Retail | PRNewsFoto via Getty Images
  • Edward Lampert hasn’t been able to right his sinking retail ship.

Edward Lampert might not be a household name like Jobs. But he is one of the least popular CEOs in the world. He’s the CEO of Sears Holdings, which controls Sears, as well as Kmart. As most of us know, both brands are in serious trouble, and Lampert’s leadership hasn’t been able to right the ship. Also, Lampert seems to feel that everything is fine, despite the warning lights flashing for the retail industry.
Next: This CEO even had a documentary made about him.

9. Roger Smith: General Motors

Former GM CEO Roger Smith
Former GM CEO Roger Smith | WDTN/Dayton
  • Roger Smith was unable to make GM competitive.

If you are familiar with the Michael Moore documentary Roger & Me, you probably know about Roger Smith. Smith was the chairman and CEO of General Motors from 1981 until 1990 and oversaw a huge change to the company’s inner workings. This included downsizing, automation, and new trade deals with foreign automakers. Ultimately, Smith’s attempts proved fruitless, and GM took a beating.
Next: This guy claimed nicotine wasn’t addictive.

8. James W. Johnston: R.J. Reynolds Tobacco Company

James Johnston, then-chairman and chief executive of R.J. Reynolds Tobacco Company, holds up a recent copy of U.S. News and World Report.
Then-chairman and CEO of R.J. Reynolds Tobacco Company, James Johnston holds up a copy of U.S. News and World Report. | J. David Ake/AFP/Getty Images
  • James Johnston said under oath that nicotine wasn’t addictive.

There have been many tobacco executives, but we’re going to zero in on James Johnston, the former CEO of R.J. Reynolds Tobacco Company. Johnston famously appeared before Congress, under oath, and declared nicotine wasn’t addictive. This, of course, was a lie. And it was one backed up by other execs who had one key interest in mind: Keep selling cigarettes at any cost.
Next: This CEO experienced disaster under his watch.

7. Tony Hayward: BP

Former BP CEO Tony Hayward answers questions from the media on an oil-stained beach.
Former BP CEO Tony Hayward answers questions from the media on an oil-stained beach. | John Moore/Getty Images
  • Tony Hayward was the CEO in charge of BP during the Deepwater Horizon disaster.

You’ll remember Tony Hayward from the Deepwater Horizon disaster. Hayward was, at the time, the CEO of BP and was thus on the hook for the disaster. The company’s clumsy and slow response to the disaster made him public enemy No. 1. An employee wrote on Glassdoor after the spill that a con to the company was “uncertainty due to the potential impact of the oil spill. A large reorganization is in the works with little communication to the employees of what it will entail.”
Hayward was eventually fired after 4.9 million barrels of oil leaked into the Gulf of Mexico. He did say he was sorry, though, for what it’s worth.
Next: This CEO made bad fiscal moves.

6. Dick Fuld: Lehman Brothers

Richard Fuld
Lehman Brothers former chairman and CEO Richard Fuld | Chip Somodevilla/Getty Images
  • Dick Fuld took Lehman Brothers down the path to bankruptcy.

Dick Fuld is another name that’s likely unfamiliar to most, but his actions (or lack thereof) had an impact on just about everybody during the financial crisis of 2008. At that time, Fuld was the chairman and CEO of Lehman Brothers and got the company thick into the weeds in subprime mortgages. That ultimately bankrupted Lehman, which was one of the first dominoes to keel over during the subprime meltdown. He earned more than $500 million during his tenure as CEO, which started in 1994.
Next: We head far back into history for this CEO.

5. Henry Frick: Carnegie Steel Company

Henry Frick
Henry Frick | U.S. National Parks Service
  • Businessman Henry Frick was against unions.

We’ll go back in time to visit Henry Frick, a ruthless businessman who remains famous for his union-busting ways and cutthroat business tactics. Frick died in 1919, but prior to that he was instrumental in the formation of U.S. Steel. He served as chairman of the Carnegie Steel Company and worked alongside many famous business figures from the time. He’s one of history’s most reviled, yet respected, businessmen.
Next: Another Wall Street exec who contributed to the recession

4. Martin Sullivan: AIG

Members of Code Pink protest former AIG CEO Martin Sullivan.
Members of Code Pink protest former AIG CEO Martin Sullivan. | Alex Wong/Getty Images
  • Martin Sullivan caused AIG to need a bailout.

We certainly aren’t done with the financial crisis of 2008, as many Wall Street execs (not just Fuld) had roles in the economic meltdown that cost so many people so much. Martin Sullivan was the CEO of AIG, and under his watch the company floundered and eventually needed to be bailed out with $180 billion from the government.
Despite that, Sullivan received a severance package most could only dream of. It included “$25.4 million, including $322,000 for private use of corporate aircraft, $153,000 for car and parking, $160,000 for home security and $41,000 for financial planning,” according to USA Today.
Next: This CEO took some bad loans.

3. Bob Nardelli: Home Depot and Chrysler

Bob Nardelli
Bob Nardelli | Bill Pugliano/Getty Images
  • CEO Bob Nardelli didn’t help Chrysler avoid bankruptcy.

Presiding over both Home Depot and Chrysler, Bob Nardelli is yet another chief executive who’s widely disliked. Nardelli’s tenure at Chrysler, which began in August 2007, was troubled. He came in right when the auto companies got into trouble, and Chrysler ended up filing for bankruptcy in April 2009. Nardelli, however, didn’t make things any easier, as he reportedly opted for more expensive loans to save the company in order to avoid an executive pay cap as a part of the deal.
Next: This former presidential candidate was forced to resign as a CEO.

2. Carly Fiorina: HP

Carly Fiorina
Carly Fiorina | Saul Loeb/AFP/Getty Images
  • HP lost about half its value under Carly Fiorina.

If you paid early attention to the 2016 presidential election, Carly Fiorina is probably a recognizable face. But before her ill-fated run for office, Fiorina served as CEO of HP from 1999 until 2005. During that time, HP acquired Compaq and also cut tens of thousands of people from its workforce. When it was all said and done, HP lost approximately half of its value, and Fiorina was forced to resign. Fiorina has had a very successful business career, by most counts, but she just didn’t make for a very good CEO at HP.
Next: This CEO is having trouble running a country.

1. Donald Trump: The Trump Organization and the United States

Donald Trump
In 2012, Donald Trump attends the Success by Trump fragrance launch at Macy’s Herald Square. | Slaven Vlasic/Getty Images
  • Donald Trump so far is the least popular president in history.

You knew he was coming — and here he is. Donald Trump — who is now, of course, the president of the United States — wasn’t always so despised. In fact, he has a 95% approval rating from 12 reviews on Glassdoor for The Trump Organization. But one former employee wrote on Glassdoor, “No upward movement. Education was discouraged. No HR in the office so upper management treated employees as they pleased. Too much playing politics.”
And speaking of playing politics, Trump’s antics and take-no-prisoners attitude during the 2016 election (and after it) have earned him a lot of ire. At this point, he is the least popular president in history. And though being president isn’t what you would think of as a traditional CEO, Trump is the chief executive of the entire country.
Additional reporting by Mary Daly.