The end of each year is a time for reflection for corporations, assessing the wins and the mistakes, the result of strategies for which there are no “give-backs.” In 2025, President Donald Trump and his policies served as the fulcrum for many companies in media and entertainment that based their moves on how best to escape his wrath or win his favor. But not all of the bad decisions in 2025 were solely because of the president.
TheWrap prides itself on having a critical eye when reporting about Hollywood, trying to make sense of ill-fated strategies and holding the companies accountable.
We are highlighting here, in no particular order, some of the biggest blunders of the year.
Disney Dropping Jimmy Kimmel
In September, the Walt Disney Co. said it was suspending production of “Jimmy Kimmel Live” indefinitely from its ABC network, citing comments the late night host made in the wake of the murder of right wing activist Charlier Kirk.
The decision came as a huge shock and left some wondering immediately whether the suspension was an attempt to appease Trump, with one of his regulators, FCC Chairman Brendan Carr, threatening to take action against ABC and its affiliates.
Kimmel’s comments raised raised hackles on the right for criticizing the response by “the MAGA gang” to the Kirk assassination, and implying the shooter might have come from that world. That led to a rising firestorm and an open threat by Carr to take action against ABC and its affiliated stations.
The fervor over the suspension wasn’t just limited to First Amendment proponents, with outrage building on social media and prompting consumers to boycott Disney businesses, including dropping subscriptions to Disney+. It was becoming clear benching Kimmel was going to have an effect on the bottom line.
Days later, Disney announced it was putting Kimmel back on the air. “It is a decision we made because we felt some of the comments were ill-timed and thus insensitive. We have spent the last days having thoughtful conversations with Jimmy, and after those conversations, we reached the decision to return the show on Tuesday.” Ooops.
- Jimmy Kimmel Suspension Is Latest Move in Trump’s Assault on Free Speech
- 5 Options for Disney to Get Out of the Jimmy Kimmel Fiasco
- Disney+ and Hulu Cancellation Rates Doubled Amid Jimmy Kimmel Suspension Saga
Rolling Back DEI
Since President Trump was inaugurated in January, major conglomerates, including Disney, Amazon, Paramount Global and Warner Bros., cut or adjusted their diversity, equity and inclusion programs. It was stunning to see how quickly studios retreated, particularly since Hollywood’s efforts in recent years focused on championing diversity. Still, many programs had already begun to be pared as more time passed from when the murder of George Floyd had elevated the Black Lives Matter movement.
Experts and advocates were quick to tell TheWrap that pulling back on DEI will ultimately leave a hole in their bottom line. “It’s a horrible business decision and certainly not the right thing to do,” Darnell Hunt, UCLA’s executive vice chancellor and provost, told TheWrap.
- Media Went All-In on Diversity. Now It’s in Full Retreat
- With DEI Rollbacks, the Business of Hollywood May Take a Hit
- As the DEI Pendulum ‘Swings Back,’ Hollywood’s Top Female Producers Stand Their Ground | Video
Lionsgate + Disney hit AI roadblocks
Granted, AI is still largely an experiment in Hollywood and a topic that is still deeply divisive. Still, some decisions for implementing artificial intelligence stand as cautionary tales. Whether it’s hyping up the capabilities of large language models that weren’t quite ready yet, or juggling actors, writers and directors who are steadfast against it, AI faced a ton of challenges.
Our managing editor Roger Cheng has documented some of the larger mishaps, but teased that AI could see significant leaps in 2026 as the technology improves and the conversations shifts to how the technology can be used as a tool vs. a way to replace people.
- What Happened to Lionsgate’s Splashy Plan to Make AI Movies With Runway? It’s Complicated | Exclusive
- How Disney’s AI Ambitions Hit a Wall | Exclusive
LA Times’ Confounding IPO Strategy
One of the year’s biggest head-scratchers was the decision by the Los Angeles Times’ billionaire owner Patrick Soon-Shiong to solicit $500 million from private investors as a pre-cursor to an IPO next year. Soon-Shiong’s tenure as owner of the once-storied paper has been by most accounts a disaster, with it reporting a net loss of $21.5 million for the first six months of 2025 while carrying short and long-term debt of $301 million. Not exactly an enticement for an investor, private or public.
“This seems to me like a way to get suckers to cover part of his exposure while he remains in control. I think the guy is basically clueless about the business and doesn’t know what he doesn’t know, which is always dangerous,” a former senior newspaper executive told TheWrap.
The Washington Post’s AI Podcast Slop Flop
The Washington Post, under the ownership of Jeff Bezos and the leadership of William Lewis, has seen its fair share of strife and negative media attention. So one might think launching any new products into the marketplace would be buttoned-up to avoid yet more criticism.
Yet the release of a new personalized AI podcast in December ended up being anything but buttoned-up, rife with embarrassing errors, like misattributing or inventing quotes and inserting commentary.
A Post spokesperson declined to comment to TheWrap, but they pointed to its public touting of the product as an early, “experimental” effort.
The post The Biggest Business Blunders in Media and Entertainment in 2025 appeared first on TheWrap.
