Name: Top 10 Most HATED CEOs of All Time
Uploaded: 2026-01-16T17:04:26.000Z
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Martin Shkreli apologized to investors and admitted he'd made mistakes as he sobbed and pleaded for leniency.

And today we're counting down our picks for the CEOs whose leadership failures caused serious, well documented harm and permanently destroyed their reputations.

We're focusing on executives whose decisions had large scale impact and earned clear blame from courts, regulators or the public.

That means we're leaving out CEOs who are simply controversial or unpopular, but

whose companies continue to succeed or whose legacies remain divided.

Poking the books to the tune of $11 billion.

Bernie Ebbers was convicted on nine felony counts in 2005.

Even though WeWork is 50 square foot per person, a third of all WeWork spaces are actually open in open common spaces that give access to everybody that we don't measure as seats.

So the way we do it is people think that WeWork is all open.

But we create a lot of common space for everybody.

Few corporate leaders managed to blend messianic ambition with financial recklessness quite like Adam Neumann, the charismatic co founder of WeWork.

He cultivated an image of a visionary leader building a co working space empire that promised to elevate the world's consciousness while racking up staggering losses at an astonishing rate.

There was an interesting piece in the New York Times over the weekend titled Adam Newman and the Art of Failing Up.

The report detailed how Adam Newman was able to create and build WeWork fail spectacularly at an attempt to go public and still walk away with a potential billion dollar payday.

It cites his ability to read people, his persuasive charisma, and his taste for risk.

Details emerged of Newman selling the trademark rights to we back to we work for nearly $6 million purchasing properties, then leasing them back to the company and even flying private jets with investors money while laying off employees.

The planned 2019 IPO, which was supposed to be a crowning achievement, instead exploded, exposed the company's unsustainable business model, leading to a dramatic valuation plunge from 47 billion to under 10 billion.

What would it take for Mark to buy this ipo?

So I've got an issue with the business model in general.

So you've got a company that's signing all these long term leases and then they're subleasing to little, you know, small businesses.

Maybe one Employee kind of companies on very short term leases.

We're sorry for the massive disruption it's caused to their lives.

And, you know, weird, there's no one who wants this thing over more than I do.

The water and all that lives in and around it could be harmed.

For years, the catastrophic Deepwater Horizon oil spill wasn't just an environmental disaster.

For BP CEO Tony Hayward, it became a personal public relations inferno.

The explosion on the offshore drilling rig in 2010 killed 11 workers and unleashed the largest marine oil spill in history, spewing millions of barrels of crude into the Gulf of Mexico, devastating ecosystems and livelihoods.

As the catastrophe unfolded, Hayward's handling of the crisis was nothing short of a public relations nightmare.

It's not just Hayward's reputation that's taken a hit.

Hayward's 623,000 shares of BP were worth almost $38 million.

His infamous plea for his life back, uttered just weeks after the spill began, exemplified his apparent detachment from the immense suffering and environmental ruin his company had caused.

Hayward was criticized for downplaying the spill's impact, for perceived arrogance during congressional hearings, and

for a general inability to convey genuine empathy.

How do you feel about this imminent change?

He was the one that allowed the company to run up the worst safety record of any oil company in the world.

Travis Kalanick, founder and CEO of ridesharing giant Uber, suddenly resigning late Tuesday after intense pressure from five major investors.

In a statement, Kalanick said, I have accepted the investors request to step aside so that Uber can go back to building rather than be distracted with another fight.

Revolutionizing an industry often requires an uncompromising vision.

But for Uber co founder and former CEO Travis Kalanick, that drive came at an immense ethical cost.

Under Kalanick's tenure, Uber was embroiled in scandal after scandal, allegations of sexual harassment and discrimination, a culture described as bro like and cutthroat, the use of gray ball software to evade regulators, and

even alleged attempts to steal trade secrets from competitors.

It is day two of the Uber vs Waymo trial, and

controversial Uber founder and former CEO Travis Kalanick took the stand.

Kalanick is the most anticipated witness at this trial, which is set to last three weeks.

And Waymo went after him over the technology at the center of this case.

His personal conduct Including a heated argument with an Uber driver caught on video, further eroded public trust.

This pileup of ethical breaches, among other factors, culminated in crushing board and investor pressure and Kalanick's eventual forced resignation in 2017.

It is not clear at this point who will take over.

Kalanick will remain on the board of directors.

We reached out to Uber tonight, but have not heard back yet.

In my wildest imagination, when I would project myself into my late 50s and early 60s, where I would be or what I would be doing if I make a list of 100 different places or 100 different things here, would never make that list.

He now earns a dollar a day mopping floors and slinging hash to his fellow inmates.

Prepare for a tale of corporate larceny so extravagant it almost reads like fiction.

Starring Dennis Kozlowski, the former CEO of Tyco International, Kozlowski epitomized the era of excessive corporate spending and blatant self enrichment at shareholder expense.

His opulent lifestyle, funded directly by company coffers, became legendary.

What's it like to earn that kind of money?

Keeping score meant keeping up with the masters of the universe.

$30 million to build a mansion in Boca Raton.

Acquiring homes in Nantucket and Colorado and just loose change.

$16 million for Endeavor A vintage yacht.

Among the most infamous expenses were a two million dollar birthday gift for his wife on the Italian island of Sardinia, complete with a gladiator ice sculpture, all paid for with Tycho funds.

His spectacular fall from grace, culminating in a 2005 conviction for grand larceny, Conspiracy and securities fraud cemented his status as a man whose avarice knew no bounds.

Would Dennis Paslowski a few years ago even contemplate and going to Europe to buy old master paintings?

You know, it came with earning the amount of money I was earning at the time.

This Theranos blood test put my cholesterol at 170.

My own doctor found it to be 169 just the week before.

Holmes says she wants to make this sort of testing available anywhere, anytime.

There's no reason why these can't be distributed in in very, very decentralized locations.

Holmes captivated investors and the public with promises of a revolutionary technology that could perform hundreds of tests from a single drop of blood.

She cultivated an almost cult like following, mimicking Steve Jobs aesthetic and speaking in a deep modulated voice.

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Top 10 Most HATED CEOs of All Time

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