20 CEOs Who Drove Their Companies Into the Ground

Sometimes, the person at the top can steer the ship right into an iceberg. These CEOs had the power, the paycheck, and the platform—and somehow managed to fumble the whole bag.

From tone-deaf decisions to ignoring reality, these executives took thriving or promising businesses and ran them straight into the ground. Remember that being in charge doesn’t always mean you know what you’re doing.

20. Ron Johnson – JCPenney

Ron Johnson, CEO of JCPenney
Wikipedia

Ron Johnson tried to turn JCPenney into Apple, forgetting that JCPenney customers wanted coupons. The rebranding backfired so hard that the company lost billions, and customers vanished.

19. John Sculley – Apple

John Sculley
Wikimedia Commons

Sculley famously ousted Steve Jobs and led Apple into a creatively stale slump. The company floundered so severely that it had to beg Jobs to return years later.

18. Marissa Mayer – Yahoo

Marissa Mayer
Flickr

Mayer came in with big plans and an even bigger paycheck, but she never quite turned the ship around. Yahoo’s slow decline continued under her watch, eventually ending in its sale.

17. Bob Nardelli – Home Depot & Chrysler

Bob Nardelli
Wikipedia

Nardelli left Home Depot with a golden parachute after alienating employees and shareholders. Then he took the wheel at Chrysler and drove it straight into bankruptcy.

16. Adam Neumann – WeWork

Adam Neumann
Wikimedia Commons

Neumann turned WeWork into a cult of personality—and an expensive one. Wild spending and questionable decisions led to one of the most dramatic startup collapses ever.

15. Leo Apotheker – HP

Leo Apotheker
Flickr

Apotheker made baffling strategic moves, including ditching HP’s core PC business and buying Autonomy for too much. It was a short and catastrophic tenure.

14. Elizabeth Holmes – Theranos

Elizabeth Holmes, founder and CEO of Theranos
Wikimedia Commons

Holmes had the charisma and the black turtleneck, but not the working tech. Her reign at Theranos ended in scandal, lawsuits, and a cautionary tale for the ages.

13. Steve Case – AOL Time Warner

Steve Case
Flickr

Steve Case masterminded the AOL-Time Warner merger, which might still be the worst corporate combo in history. Billions were lost, and egos were bruised.

12. John Antioco – Blockbuster

John Antioco
Wikimedia Commons

Antioco passed on buying Netflix for peanuts and focused on late fees instead. Blockbuster didn’t just miss the boat—it sank while streaming sailed off.

11. Martin Winterkorn – Volkswagen

Martin Winterkorn
Wikimedia Commons

Winterkorn’s watch included the infamous emissions cheating scandal. The fallout cost VW billions and wrecked its reputation globally.

10. Tony Hayward – BP

Tony Hayward
Flickr

Hayward’s leadership during the Deepwater Horizon disaster was as disastrous as the spelling. His “I want my life back” comment didn’t help either.

9. Carly Fiorina – HP

Carly Fiorina
Flickr

Fiorina’s mega-merger with Compaq was supposed to make HP unstoppable. Instead, it created chaos, lost jobs, and tanked morale.

8. John Chen – BlackBerry

John Chen
Flickr

Chen bet big on software just as BlackBerry’s hardware was gasping for air. It was too late for a company that once ruled the mobile world.

7. Jeffrey Skilling – Enron

Jeffrey Skilling
Wikipedia

Skilling was the architect of Enron’s “innovative” accounting practices. His leadership ended with a prison sentence and one of the most notorious collapses in corporate history.

6. Brian Dunn – Best Buy

Brian Dunn
Youtube-BSR

Dunn oversaw shrinking sales, closing stores, and an internal scandal simultaneously. It was a dark chapter for what was once the go-to electronics giant.

5. Dennis Kozlowski – Tyco

Former Tyco C.E.O. Dennis Kozlowski (right)
Flickr

Kozlowski turned Tyco into his ATM, buying yachts and throwing million-dollar birthday parties. His greed caused the company to fall apart.

4. Travis Kalanick – Uber

Travis Kalanick
Flickr

Kalanick helped build Uber into a powerhouse, but the toxic culture he fostered nearly tore it down. Investors eventually forced him out to save the brand.

3. Kenneth Lay – Enron

Kenneth Lay, the founder and former CEO of Enron
Wikipedia

Lay’s leadership was all smiles and spin until the truth came out. Enron’s collapse exposed massive fraud and became a business school horror story.

Read More: 20 CEO Blunders That Turned Into Full-Blown Nightmares

2. Richard Fuld – Lehman Brothers

Richard Fuld
Flickr

When Lehman Brothers collapsed during the 2008 financial crisis, Fuld was at the helm. His decisions helped ignite a global recession and wiped out a 158-year-old firm.

Read More: Scandal in the Corner Office: 10 CEOs Who Totally Blew It

1. Sam Bankman-Fried – FTX

Sam Bankman-Fried
Wikimedia Commons

SBF was the crypto wunderkind until everything crashed spectacularly. FTX’s implosion was a chaotic blend of mismanagement, hubris, and alleged fraud.

Read More: 10 Rising Power Players Who Could Be the Next Billionaires

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