Anna Wintour has voiced her support for the newly appointed editor-in-chief of CBS News, Bari Weiss. “Clearly, she’s an accomplished young woman with a commanding personality and a distinct perspective,” Wintour commented to Variety during the Only Make Believe 25th Anniversary Gala in New York City on Monday night. “Such traits often contribute to effective leadership.”
Wintour has been at the helm of Vogue’s U.S. edition since 1988, a role she maintained for 37 years. Chloé Malle, the daughter of actor Candice Bergen and director Louis Malle, recently succeeded her as the head of editorial content for U.S. Vogue in September.
Wintour remarked, “My schedule is quite busy,” affirming her ongoing responsibilities as the chief content officer of Condé Nast and global editorial director of Vogue.
When asked if she envisions a time when she may retire, the 75-year-old fashion powerhouse responded, “That moment hasn’t come yet.” Wintour was honored with the James Hammerstein Award at the annual charity gala, hosted by John Oliver at the Shubert Theater, raising over $1.3 million to support interactive theater initiatives for children in hospitals and special education facilities across the East Coast.
Just the day prior, Oliver devoted an episode of his HBO show Last Week Tonight to exploring Weiss’ career, highlighting articles from her platform, The Free Press, which he described as “poorly fact-checked,” raising concerns about Weiss’ lack of traditional newsroom experience.
“Of course, I was aware of what was being produced at The Free Press beforehand, and that’s acceptable,” Oliver shared with Variety. “The issue arises when someone oversees a news organization without a journalism background.”
Weiss transitioned from her role as an op-ed editor at The New York Times after departing the conventional media outlet in 2020 to establish The Free Press. Last week, Paramount Skydance CEO David Ellison revealed plans for his company to purchase Weiss’ Free Press for $150 million, a decision that’s elicited mixed reactions throughout the media landscape.
While Oliver expressed grave concerns regarding the future trajectory of CBS News, he stressed the importance of distinguishing Weiss’ new position from the diligent work undertaken by the network’s journalists.
“What’s alarming is the remarkable work being produced at CBS,” Oliver asserted to Variety. “They will continue to excel until a potential worst-case scenario occurs, where individuals begin losing their jobs or resigning. Until then, I firmly want to champion the great work being accomplished at CBS News. I hope that can persist, despite the circumstances. I fear it may change.”
John Oliver on Donald Trump’s response to the shifts in power at CBS News and Paramount: “He’s certainly pleased about Ellison taking charge of Paramount and CBS. So this is more of that.” pic.twitter.com/HzUSvrLdyM
— Variety (@Variety) October 14, 2025
Former President Donald Trump remarked on Sunday that he sees “great potential” in CBS News following the merger of Skydance and Paramount, which placed David Ellison at the helm of the media company.
“I’m sure he’s pleased,” Oliver commented. “He’s certainly enthusiastic about Ellison’s leadership over Paramount and CBS. So, this is another instance of that. I doubt his happiness is ever purely genuine.”
Concluding, Oliver stated, “Generally, if he expresses genuine happiness about something, it’s worth questioning the validity of that subject.”
