In a heated appearance on CNN’s NewsNight Tuesday, entrepreneur and Shark Tank star Kevin O’Leary reportedly issued a blistering rebuke of CBS’s Late Show host Stephen Colbert for launching an explicit attack on President Donald J. Trump — and predicted that CBS won’t let the late-night comedian finish out the week.
O’Leary’s remarks came after Colbert kicked off his monologue Monday night with a profane outburst, telling the president of the United States, “Go f— yourself!”
The outburst followed CBS’s announcement that The Late Show would be coming to an end in May of next year — a move that surprised many in the entertainment world but may have just become more urgent.
“Here’s the problem for Colbert,” O’Leary said. “His contract is a payout contract through a transaction where there’s a change of control. Only a moron would tell the president to F off before he gets his check.”
O’Leary, known for his no-nonsense business acumen, made clear that Colbert’s politically charged tirade wasn’t just distasteful — it was stupid business.
While CBS has said that Colbert will remain on air through next May, O’Leary dismissed that timeline as implausible. “So what’s gonna happen now, in my opinion, is tomorrow, CBS — his boss — will fire him, and they will litigate for the next five years his payout,” he said.
For O’Leary, this wasn’t just about one offensive monologue — it was about professionalism, contracts, and accountability.
“Get rid of this guy!” O’Leary added. “If I were them, I’d whack this guy tomorrow.”
WHOA: Kevin O’Leary predicts CBS will FIRE Stephen Colbert TOMORROW instead of letting him finish out his contract.
Remind me in 24 hours if this comes true.
“Only a moron would tell the president to F off before he gets his check. So what’s going to happen now, in my opinion,… pic.twitter.com/TP42dy9C6B
— The Vigilant Fox 🦊 (@VigilantFox) July 23, 2025
The controversy points to a broader divide in American media and culture, where increasingly, late-night television hosts have abandoned comedy in favor of partisan hostility — usually aimed at conservative figures and, above all, Donald Trump.
Colbert, a longtime critic of the former and current president, has made Trump-bashing a central feature of his show for years. But even by those standards, Monday’s remarks were a departure — brazen, coarse, and deeply disrespectful.
For many viewers — and evidently for CBS executives — the question is no longer whether this kind of rhetoric is acceptable, but whether it’s worth the fallout.
With network ratings under pressure and advertisers more cautious than ever, the risk-reward calculus of Colbert’s brand of “resistance comedy” appears to be shifting.
O’Leary’s prediction — that Colbert may be fired immediately and locked in litigation over the remainder of his contract — reflects a growing sense that corporate media may finally be running out of patience with the costly divisiveness of its liberal stars.
Whether CBS moves swiftly to remove Colbert or waits out his contract remains to be seen. But what’s increasingly clear is that for networks in the Trump era, unchecked hostility toward a sitting president — especially when it turns vulgar — may no longer be a survivable business model.
[READ MORE: Trump Claims Other Liberal Comedians to Soon be Fired In Wake of Colbert Cancellation News]
