Kevin O’Leary, investor and Shark Tank star, took aim at Democratic Rep. Alexandria Ocasio-Cortez on CNN Friday night, calling her “the American nightmare.” But host Abby Phillip quickly pushed back — with a sharp dose of reality about what the American dream really means to most Americans.
O’Leary’s comment came after CNN host Abby Phillip asked if he was worried that Ocasio-Cortez — a rising star in progressive politics — could become the Democratic presidential nominee in 2028.
“I have a tremendous amount of respect for her,” O’Leary said. “But she embodies the American nightmare.”
Pressed to explain, he claimed, “Because she doesn’t believe people should succeed in wealth.” He argued that America should celebrate financial success, and said Ocasio-Cortez’s criticism of billionaires threatens that ideal.
Phillip wasn’t having it. She pointed out that Ocasio-Cortez came from “a very modest background” — a Bronx-born former bartender who won a seat in Congress.
“She does not support capitalism,” O’Leary fired back.
Phillip hit him with a sharp rebuttal: “There are many Americans who work really hard and their aspiration is not to become supremely wealthy. It is to have strong family units, it is to have community, it is to have a sense of purpose, it is to contribute to their environment.”
“There are many Americans for whom just being filthy rich is not the American dream,” she added.
O’Leary rolled his eyes: “I want to forgive you, but you are making it hard.” Earlier, he said Phillip’s view “tainted the American dream.”
The moment lit up social media. Critics slammed O’Leary as out of touch, saying he ignored the real struggles facing working Americans. Online, many argued that wealth isn’t the only version of success.
While some still see the American dream as making it big financially, research shows the picture is more complicated.
A Pew Research study found only 42% of Americans under 50 think the dream is achievable, compared to 68% of those 65 and older. And only 39% of low-income Americans believe the dream is still alive, compared to 64% of high earners.
Experts say the dream looks different depending on who you are.
“Unless Mr. O’Leary is willing to call 250 years of American criticism of wealth inequality an ‘American nightmare,’ I suggest he reconsider his critique,” said Rutger Ceballos, a political science professor at the University of Oregon. He pointed out that skepticism of extreme wealth dates back to the American Revolution.
Other experts agree that capitalism has helped some but left others behind.
“The American dream doesn’t mean the same thing for everyone,” said Sunyee Yoon, a marketing professor at the University at Buffalo. For many, she said, the dream is simply “a safer, more stable life” — not luxury cars or stock portfolios.
For people in low-income communities, it might mean a job that offers healthcare or being able to attend college without crushing debt. For immigrants, it could be safety and freedom. For marginalized groups, it’s about dignity and equal opportunity.
Megan Hyska, a philosophy professor at Northwestern, said O’Leary’s version of the dream is misleading. “This is a sleight of hand that equates the widespread dream of material security with the elite dream of unregulated wealth acquisition,” she said.
Watch the exchange below from CNN:
O’Leary: People come to America to achieve the American dream. She embodies the American nightmare.
Phillip: What if some Americans think the most important thing is not the rich getting richer?
O’Leary: You just tainted the American dream with that statement. You tainted what… pic.twitter.com/1qU6ORNQvx
— Acyn (@Acyn) April 26, 2025
