“The course of true love never did run smooth.” – William Shakespeare
Some CEOs get a little too used to the people around them always saying yes.
Maybe this explains why they sometimes blow it all on love, or lust, or blatant sexual harassment.
Here’s a look at top CEOs who’ve lost their high-paying jobs for office naughtiness.
These are just some of the guys who got caught. And to think they were paid millions for their judgement.
Kohl’s CEO Ashley Buchanan – May 2025
Struggling retailer Kohl’s gave Ashley Buchanan a $20 million compensation package in hopes he could reverse its sagging fortunes. He was fired three months later for reportedly steering millions of dollars in business to his girlfriend.
“Before I took the job was when I assessed the entire business, I just saw opportunity, right?” Buchanan said in a March 2025 conference call.
Opportunity knocked … and it knocked Buchanan right out the door.
Read more: Million-Dollar Baby
Norfolk Southern CEO Alan Shaw – September 2024
Never give your critics ammunition. Alan Shaw made this crucial mistake by having a tryst with the railroad’s Chief Legal Officer Nabanita Nag.
Activist shareholders were gunning for Shaw’s resignation as the railroad’s financial performance slid off off the tracks. Union employees were steamed about him, too. He was especially under pressure after a train derailment decimated East Palestine, Ohio, spilling 100,000 gallons of hazardous materials and costing the company about $1.7 billion.
Shaw kept his job through all of this, but his affair – which was against the corporate ethics policy and rife with conflicts – did him in.
What a train wreck.
Read more: Drivin’ That Train
Comtech CEO Ken Peterman – March 2024
A CEO who has an affair with an underling cheats on his company, his shareholders and often his spouse in a single folly. Ken Peterman may be a case in point.
The company wouldn’t say why it fired him last year, but it all came out after Peterman was arrested on insider trading and securities fraud charges in December 2024.
Before this series of blunders, Peterman was a well-respected aerospace and defense executive.
Comtech’s annual report once touted a line from a cloying profile on him: “Unique and visionary leadership through integrity, passion, and innovation are the qualities that define Ken Peterman.”
Integrity is something you have. Not something to tout in your annual report.
Read more: A CEO’s Road To Hell
[[[Don’t Miss These Blunders]]]
Helios Technologies CEO Josef Matosevic – July 2024
Josef Matosevic ran a company that provided electronic controls technology, but he couldn’t control himself.
The company said it replaced him following an investigation into his consensual relationship with an employee.
“The Board does not tolerate any actions that are inconsistent with our Company’s values and code of conduct and upon notification of the allegations, took swift and decisive action,” the board’s chairman said in a press release.
Yeah, but for Helios, this was hardly the first time.
The company fired a previous CEO Wolfgang Dangel in April 2020 for the same thing.
Read More:
Helios Technologies Provides Update on Leadership Transition
Helios Technologies Announces Leadership Transition
BP CEO Bernard Looney – September 2023
Some CEOs treat their companies like a dating app.
BP CEO Bernard Looney resigned following an internal investigation that revealed not one, but multiple dalliances with colleagues. Looney was hired as a drilling engineer in 1991. He became CEO in 2020.
In an earlier investigation, he admitted to having affairs but didn’t disclose them all.
“All leaders in particular are expected to act as role models and to exercise good judgement in a way that earns the trust of others,” the London-base petroleum giant explained in a press release.
All that lovin’ cost him $40 million in severance.
Read more:
BP’s former CEO is forfeiting $40 million in severance for misleading company board
CBOE Global Markets CEO Edward Tilly – August 2023
Edward Tilly joined CBOE as a floor trader in 1987 and worked his way through the ranks to become CEO in 2013.
He resigned after the board found he failed to disclose “personal relationships with colleagues.”
There was no telling how many relationships, but the trading company executive must have figured he had options.
Read more: Cboe Global Markets Announces Leadership Transition
NBCUniversal CEO Jeff Shell - April 2023
Comcast fired the head of NBCUniversal after an internal investigation corroborated allegations of sexual harassment and discrimination.
Jeff Shell had this much to say about it:
“I had an inappropriate relationship with a woman in the company, which I deeply regret. I’m truly sorry I let my Comcast and NBCUniversal colleagues down, they are the most talented people in the business and the opportunity to work with them the last 19 years has been a privilege.”
An “inappropriate relationship?” The company called it “sexual harassment.”
Was the Peacock streaming the wrong content?
Take The Tour: The Business Blunders Hall of Shame
Barclay’s CEO Jes Staley - November 2021
Jes Staley stepped down as CEO of Barclays after the British banking giant uncovered his ties to the infamous late sex offender Jeffrey Epstein.
Later, Staley admitted in court that he had consensual sex with one of Epstein’s staffers. But he claimed he had no knowledge of the twisted financier’s “monstrous activities,” trafficking underaged girls to wealthy pedophiles.
In a 2010 email chain, Staley reportedly told Epstein: “That was fun. Say hi to Snow White.” Epstein asked, “What character would you like next?” Staley replied: “Beauty and the Beast.”
It could have been worse. At least he didn’t ask for the “Little Mermaid.”
Read on: Former JPMorgan and Barclays exec Jes Staley tells court he slept with Epstein assistant
McDonald’s CEO Steve Easterbrook – November 2019
Mickey D’s fired its CEO Steve Easterbrook for a consensual relationship with an employee in November 2019. Several months later, an internal investigation uncovered even more inappropriate relationships with employees.
Then in 2023 the Securities and Exchange Commission fined Easterbrook $400,000 for allegedly lying about the terms of his firing in an attempt to keep his massive severance benefits.
Easterbrook ended up losing a $105 million severance package.
They say money can’t buy you love, but that would have been enough to buy more than 20 million Happy Meals.
Read more:
McDonald's Corporation Announces Leadership Transition
SEC Charges McDonald’s Former CEO for Misrepresentations About His Termination
Intel CEO Brian Kranzanich – June 2018
Brian Kranzanich stepped down from Intel after the chipmaker learned about his past consensual relationship with an employee.
“An ongoing investigation by internal and external counsel has confirmed a violation of Intel’s non-fraternization policy, which applies to all managers,” the company said.
The affair began a decade earlier and ended before he was named CEO in 2013, but it cost him a fortune once it was finally uncovered.
Kranzanich was making upwards of $21 million a year and enjoyed a generous package of perks, including transportation and personal security.
“That’s the power of Intel inside.”
Read more:
Intel CEO Brian Krzanich Resigns, Board Appoints Bob Swan as Interim CEO
Maybe they just couldn’t score a date for the prom
Sometimes I wonder if maybe some of these guys were zit-faced geeks who couldn’t get a date for their high school proms. Then one day they got promoted to CEO and suddenly fancied themselves love machines.
It’s a common problem with out-of-check egos.
Going back further, here’s a list of more CEOs who found themselves lost in love.
As Nazareth sang, "Love Hurts".
A take as old as time…