‘Read the room’: Kevin O’Leary says Kimmel's 'political trouble' is what can come if comics 'push the envelope' — but he thinks it'll 'resolve itself'

“My attitude is I stay in my lane, I do my job, and I read the room. And I think those that don’t do that find themselves in precarious positions,” he told Moneywise during a wide-ranging conversation on Sept. 19.

Want the full Kevin O’Leary conversation? Subscribe now to watch all our latest interviews before anyone else

Mr. Wonderful reflected on the careful balancing act comedians must perform.

“Going all the way back, for comics in the ’50s that got themselves in political trouble, it’s a very difficult profession because you have to be able to read the room, read society, read the tone of what’s out there in the market and, you know, that’s not easy,” he said. “It’s not just Kimmel — lots of them get into trouble because they push the envelope too far.”

O’Leary said he was optimistic the “very difficult situation” would ultimately “resolve itself.” His comments came five days before Kimmel’s show returned on Tuesday night.

The Kimmel affair, and O’Leary’s response to it, demonstrate how much short-term volatility can be produced when private businesses, even large and powerful ones, clash in the public square with politicians and government.

It’s something every investor needs to be aware of.

Kimmel in the crosshairs

On Monday, the Walt Disney Co., ABC’s parent, announced that Kimmel’s show would return Tuesday night [1] after a weeklong suspension over Kimmel’s controversial on-air comments about the killing of conservative activist Charlie Kirk, an ally of President Donald Trump (whose initial take on the situation was that Kimmel had been “fired for lack of talent”).

The suspension came in response to criticism and barely veiled threats from Federal Communications Commission (FCC) Chairman Brendan Carr, a Trump appointee.

“We can do this the easy way or the hard way,” Mr. Carr said on a Sept. 17 podcast appearance. “These companies can find ways to change conduct and take action, frankly, on Kimmel, or there’s going to be additional work for the FCC ahead.” [2]

Two groups of local ABC station affiliates, operated by the companies Nexstar and Sinclair, did not air Kimmel’s comeback show on Tuesday, during which the host delivered an emotional monologue addressing the situation.

“Notably, this is the first time recently that any local TV stations have pushed back on a national programmer like Disney,” Carr posted on Tuesday on X. “And that is a good thing because we want empowered local TV stations.” [3]

Meanwhile, Trump has implied, via posts on Truth Social, that the White House may pursue legal action against Disney and ABC over the reinstatement.

Comedians in hot political water

O’Leary said that comics getting in political trouble isn’t a new phenomenon and suggested they would be wise to steer clear of politics.

He recalled comments he claimed were made by comedy legend Johnny Carson that stood out to him.

“He said, ‘Every day, every single day when we write our show, we look at the opportunity to get involved in politics and I squash it. I kill it. And I do that because why would I want to p–s off 50% of my audience?’ I thought that was brilliant. It made so much sense.”

It’s not clear whether Carson, who hosted The Tonight Show from 1962 to 1992, said those precise words, but he did appear on CBS’ 60 Minutes in 1979 and was asked if he gets sensitive about the fact that people say he’ll “never take a serious controversy.” [4]

"That's not what I'm there for. Can't they see that?" Carson said. "Once you start that, you start to get the self-important feeling that what you say has great import. And you know, strangely enough, you could use that show as a forum. You could sway people. And I don't think you should, as an entertainer."

O’Leary also referenced basketball star Michael Jordan’s famous quote, "Republicans buy sneakers, too." In 1990, Jordan had been asked to endorse a Democratic candidate in the U.S. Senate race in North Carolina, his home state, but he refused.

Of course, there are also many who believe one of the core responsibilities of comics is to challenge authority, and Kimmel received vehement support from prominent show business figures, politicians and others concerned about free speech violations and the potential chilling effect of an overzealous FCC.

Even former Disney CEO Michael Eisner asked on X, “Where has all the leadership gone? If not for university presidents, law firm managing partners, and corporate chief executives standing up against bullies, who then will step up for the first amendment?” [5]

What’s at stake

Last year, ABC agreed to pay $15 million toward Trump’s presidential library to settle a defamation lawsuit, even though the network had a good chance of winning in court. This time it looks like the company is choosing resistance.

Disney stock took a noticeable hit following the Kimmel suspension, as many social media users claimed they were canceling their subscriptions and selling shares [6]. Prices then rallied on the news that the show would be coming back.

This saga reminds investors that certain categories of stocks, including those of media conglomerates like Disney, can be susceptible to volatility arising from public scandals, disputes with politicians and public boycotts.

Target’s shares have plunged amid a boycott over its scaling back of diversity, equity and inclusion (DEI) initiatives, which the Trump administration has frequently and loudly opposed. The retail giant’s CEO recently announced he would step down.

Shares in electric car company Tesla have also been impacted this year as its CEO Elon Musk engaged in a public feud with the president shortly after having presided over the administration’s “DOGE” cost-cutting frenzy in the spring.

In the case of the Kimmel controversy, the timing of ABC’s actions is notable given other major happenings involving its storied parent company.

Disney is merging its Hulu + Live TV service with Fubo TV. ESPN, another Disney subsidiary, has also recently signed a blockbuster deal with the NFL. Both deals will require regulatory approval from the federal government. [7]

Nexstar, the largest television station operator in the country, also has a mega business deal to think about. It wants to buy Tegna, another local TV operator, for $6.2 billion, which would require the FCC to abolish a rule that caps the number of households a single company can reach with local stations at 39%.