There may be a new entrant in the annals of corporate hole-digging: Media titan Paramount, which owns CBS and recently said it’s canceling the top-rated “Late Show with Stephen Colbert.”

Paramount said it needs to cancel the Colbert show for “financial reasons” and leaked reports likely sourced to the company suggest the show loses around $40 million per year. But the decision reeks of Trumpian subterfuge, putting Paramount in the fraught corporate position of picking sides in one of President Trump’s many disputes over business and cultural priorities.

Paramount plans to merge this year with media firm Skydance, to help stabilize its finances and ease the transition from legacy media behemoth to a nimbler streaming operation. The two companies agreed on the $8 billion deal last year, when Joe Biden was president. The Securities and Exchange Commission approved the deal in February. That left the Federal Communications Commission, which must also sign off since the deal involves the transfer of broadcast licenses.

FCC approval was “widely seen as a formality,” as Deadline reported in April. But it didn’t come until July 24, months later than would have been likely under any president other than Trump. In the meanwhile, Paramount paid tribute to Trump in unprecedented ways likely to dog the company for months or years, with the cancellation of Colbert’s show fueling a barrage of criticism from Colbert himself and many allies, some of it on Paramount’s own airwaves.

Paramount clearly didn’t anticipate this sort of trouble when it arranged the deal last year. But when Trump won the presidency in November, Paramount faced new barriers to a buyout that otherwise might have been routine. That’s because of Trump’s personal beef with CBS and the news show “60 Minutes.” Trump sued the network last year as an individual, claiming the show distorted a 2024 interview with Kamala Harris, Trump’s foe in the presidential election, to give her favorable treatment.

Shortly after taking office in January, Trump appointed loyalist Brendan Carr to head the FCC. Then Trump converted the formerly independent agency into an arm of the White House’s policy and political operations. One of Carr’s first moves as Trump’s FCC boss was opening an investigation into the CBS for its interview with Harris, an unprecedented effort to use government power to intimidate a news organization.

“The chairman of the FCC has cagily created a new and coercive technique for operating outside the agency’s established statutes and procedures to attack corporate decisions he and Donald Trump do not like,” former FCC commissioner Tom Wheeler, now of the Brookings Institution, wrote in February. “Prime targets are media company editorial decisions.”

Heather Cousinsspeaks at the SAVE COLBERT! solidarity rally and petition delivery to CBS on July 23 in New York City. (Eugene Gologursky/Getty Images for Progressive Change Campaign Committee) · Eugene Gologursky via Getty Images

The Los Angeles Times and other news organizations reported that Shari Redstone, non-executive chair of umbrella company Paramount Global, pushed her executives to settle with Trump. Redstone and her family stand to net about $1.75 billion from the Skydance deal. So she has a clear interest in pushing barriers to the deal out of the way. That may explain why earlier this month, Paramount and CBS agreed to settle the Trump lawsuit for $16 million.

Colbert roasts Trump regularly on his show and is far more political than David Letterman, whom he replaced in 2015. On July 14, the cheeky host called the $16 million Paramount payment to Trump “a big, fat bribe”—on CBS’s own air.

Three days later, Paramount canceled Colbert’s show. There’s no public evidence that the company axed Colbert to appease Trump. Yet it did please Trump. “I absolutely love that Colbert got fired,” Trump posted to social media on July 18.

Then on July 24, Paramount received the FCC blessing to close the deal with Skydance. Mission accomplished … Except for what is sure to be a very messy aftermath. Colbert’s contract lasts until next May (same as the tenure for embattled Federal Reserve Chair Jerome Powell), and the show will air until then. “For the next 10 months, the gloves are off,” Colbert told his audience on July 21.

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Colbert cronies Anderson Cooper, Andy Cohen, Jimmy Fallon, Seth Myers, Jon Stewart, John Oliver, Adam Sandler, Christopher McDonald, Lin-Manuel Miranda, and Weird Al Yankovic joined that show for a spoof that ended with a Trump-Paramount kiss-cam exposé.

The same day, Jon Stewart devoted half of his weekly Comedy Central program to blasting Paramount for trying to “make yourselves so innocuous, that you can serve a gruel so flavorless, that you will never again be on the boy king’s radar.” Stewart ended the show with a musical number, backed by a gospel quintet, featuring the refrain “Go f— yourself,” which may or may not become an instant classic but is certainly giggly.

Stewart’s show, like Colbert’s, runs on a network owned by Paramount. So does the animated series “South Park,” which just debuted the premiere episode of its 27th season, in which a fictional Trump tries to seduce a [fictional] Satan, who mocks fictional Trump for having diminutive [fictional] genitalia.

Maybe Paramount won the battle. But will it win the war? Will Trump really be satisfied that Colbert’s Paramount-supported mockery of him might continue until next year? Or that Stewart and the diabolical “South Park” brain trust will keep tweaking him indefinitely? If Paramount cites contractual obligations requiring it to continue airing the Trump-bashing resistance, will Trump nod and say, right, of course?

NEW YORK CITY - JULY 21: The Late Show with Stephen Colbert during Monday's July 21, 2025 show. (Photo by Scott Kowalchyk/CBS via Getty Images)
Ten more months of Trump bashing: ‘The Late Show with Stephen Colbert’ during the July 21 show. (Scott Kowalchyk/CBS via Getty Images) · CBS Photo Archive via Getty Images

Big public companies make mistakes all the time.

The memorable ones are those compounded by a corporate reaction that amplifies the original sin and makes everything worse. In 2023, Target tried to back away from its own LGBTQ outreach effort, offending the very people it was wooing and making no new friends in the process. In 2017, United Airlines appeared to defend thuggish security guards who forcibly dragged a passenger off a plane, igniting a firestorm of bad publicity that wiped nearly $1.5 billion off its market value. Uber co-founder Travis Kalanick resigned as CEO in 2017 after failing to shake months of controversy over a toxic company culture rife with sexual harassment and discrimination.

Those incidents are now textbook examples of how to worsen a crisis, rather than fix it. Paramount now seems headed toward its own chapter in that cringy volume.

Colbert, Stewart, et al. won’t do Trump any harm, since they’ve been slamming him for years and have long been speaking to like-minded audiences. But now they’re aiming their comedic lances at Paramount, which most of their viewers have probably never thought much about. That will change.

Rick Newman is a senior columnist for Yahoo Finance. Follow him on Bluesky and X: @rickjnewman.

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