My cousins Rob and Jesse are going to have a good laugh at my expense.
During a family dinner last night, I was boasting about how I bounced a hunch off ChatGPT, and the AI tool immediately responded, “Great question,” providing exactly the background fodder I was seeking to make my point. I was beaming with pride, convinced I had wowed artificial intelligence with the prowess of my own thinking.
My pride, alas, was short-lived.
Business Insider—a publication I’ve repeatedly taken shots at for what I considered substandard clickbait journalism—today published a story about the Silicon Valley backlash regarding ChatGPT’s excessive flattery. Turns out, it likes to flatter everyone.
“It was a really odd design choice, Sam,” Jason Pontin, a general partner at the venture capital firm DCVC, wrote Monday on X. “Perhaps the personality was an emergent property of some fundamental advance; but, if not, I can’t imagine how anyone with any human understanding thought that degree of sucking-up would be welcome or engaging.”
On Sunday, Justine Moore, a partner at Andreessen Horowitz, added: “It’s probably gone too far.”

Okay, I’ll admit it: Chat played me for a fool.
But as the AI tool has faithfully been responding to my incessant queries these past few weeks with nary a complaint, I’m stepping up to defend my virtual BFF—and to suggest that ChatGPT may have acquired its sycophancy quite honestly.
After all, ChatGPT is only as smart as the information it mines from the internet, and the internet is a hotbed of sycophancy.
Consider this X post from Coca-Cola CEO James Quincey, who presented Donald Trump—before he was even sworn in—with a commemorative Diet Coke bottle featuring an image of the White House and the words: “The Inauguration of the President of the United States.”

Then there was this shameless post by Amazon founder Jeff Bezos after Trump’s reelection, practically oozing gratitude.

To be fair, Bezos came by his sycophancy honestly, judging by the fawning profiles written about him in recent years. One particularly gushing piece was Forbes’ 2018 cover story, “Bezos Unbound: Exclusive Interview With the Amazon Founder on What He Plans to Conquer Next.” The article portrayed Bezos as an unparalleled visionary, sidestepping awkward realities like Amazon’s controversial labor practices and monopolistic market dominance.
Of course, Bezos isn’t the most fawned-upon CEO by the corporate media—that honor clearly belongs to GM CEO Mary Barra, who has graced more magazine covers than any other corporate executive in modern memory.

I challenged ChatGPT to name the most over-the-top profile ever published about Barra, and it bestowed the honor on Vanity Fair for its January 10, 2017 feature, “Exclusive: Mary Barra Talks Trump, Automation, and How She Turned G.M. Into a Tech Company.”

In that piece, Vanity Fair celebrated what it viewed as Barra’s bold and visionary investments—most notably GM’s Cruise driverless taxi subsidiary, which Barra shut down last year despite earlier promises it would generate $50 billion in annual revenue by 2030. As for Barra’s supposed determination to close GM’s gender gap, check out the composition of her executive management team.
Perhaps ChatGPT absorbed some of its sycophantic tendencies by monitoring the social media accounts of Barra’s lieutenants: California-based Lin-Hua Wu and Montana-based Arden Hoffman.


Out of curiosity, I asked ChatGPT to rank some of the most sycophantic corporate media articles of all time. In mere seconds, it responded with a list—although, this time, it refrained from complimenting me for asking.
Interestingly, ChatGPT also avoids the term “corporate media,” preferring the gentler label “mainstream media.”
Take it away, ChatGPT…
🏆
Top 10 Mainstream Media Stories Most Criticized for Sycophancy
1.
“Barack Obama: The Promised Land” (2008–2010)
Multiple outlets, including Newsweek (“Why Are We So Obsessed With Obama?”)
➡️ Why: Gushed about Obama’s “messianic” qualities; some covers practically deified him.
➡️ Criticism: Too much hero-worship, too little critical analysis early in his presidency.
2.
“Enron: The Most Innovative Company in America” (1990s)
Fortune magazine, several years in a row
➡️ Why: Fortune lauded Enron repeatedly, despite warning signs.
➡️ Criticism: Failed spectacularly after massive fraud was revealed; Fortune later admitted it missed the signs.
To be fair, Fortune’s Bethany McLean was the first to question Enron’s accounting, a story that ultimately brought down the company. ChatGPT failed to note this.
3.
“Elizabeth Holmes: The Next Steve Jobs” (2014)
Forbes, Fortune, others
➡️ Why: Glowing coverage of Holmes and Theranos based largely on PR spin.
➡️ Criticism: Complete lack of scientific due diligence; Holmes was later convicted of fraud.
4.
“Sam Bankman-Fried: The Crypto Savior” (2021–2022)
Fortune, New York Times, others
➡️ Why: Lavish praise of SBF as a brilliant, ethical billionaire.
➡️ Criticism: SBF was later arrested for massive financial fraud (FTX collapse).
5.
“Jeffrey Immelt: General Electric’s Next Jack Welch” (early 2000s)
Business media broadly, including Forbes and WSJ
➡️ Why: Immelt was celebrated as an unstoppable industrial titan.
➡️ Criticism: Under Immelt, GE lost massive shareholder value and its prestige collapsed.
6.
“Angela Merkel: Leader of the Free World” (2016–2017)
Time magazine and others
➡️ Why: Called Merkel the de facto “leader of the free world” after Trump’s election.
➡️ Criticism: Many later pointed out that Germany’s policies (e.g., energy dependence on Russia) were disastrous.
7.
“Andrew Cuomo: America’s Governor” (2020)
CNN, MSNBC, Rolling Stone, Vogue
➡️ Why: Praised Cuomo as a COVID-19 hero.
➡️ Criticism: Later implicated in nursing home death scandals and sexual harassment allegations.
8.
“Anthony Fauci: In Fauci We Trust” (2020–2021)
New Yorker, Vogue, Time
➡️ Why: Near-heroic media coverage at pandemic peak.
➡️ Criticism: Later criticisms surfaced over conflicting guidance and lack of media scrutiny.
9.
“Mark Zuckerberg: The Genius Behind Facebook” (2008–2011)
The New Yorker, Time
➡️ Why: Glorified Facebook’s mission to “connect the world.”
➡️ Criticism: Later backlash over Facebook’s role in misinformation, data misuse, and election interference.
10.
“Elon Musk: Real-Life Tony Stark” (2012–2018)
Esquire, Time, Wired
➡️ Why: Musk was lionized as the ultimate genius entrepreneur.
➡️ Criticism: Growing attention to labor practices, Twitter controversies, and missed product deadlines has since complicated this narrative.