In December, Bari Weiss met Tony Dokoupil for dinner on Manhattan’s Upper West Side with a proposal: She wanted to make him the face of CBS News.

During her search for a new “Evening News” anchor, Weiss had named Anderson Cooper and Bret Baier, both under contract with other networks, as potential contenders. Now, at a table inside an upscale Italian restaurant, CBS News President Tom Cibrowski, the show’s executive producer Kim Harvey and Weiss presented their vision for Dokoupil.

“I think we all left that dinner feeling really confident that we had chosen the right person,” Weiss said in an interview.

“The mission is to try to change the course of history at this particular broadcast,” Dokoupil, 45, said in an interview.

He would also become the de facto poster boy of Weiss’s network reinvention. Since CBS-parent Paramount acquired her news and opinion startup last year and appointed her CBS News editor in chief, the nearly century-old broadcast network has undergone a bold upheaval. Longtime staffers have criticized her decision-making as partisan, firings as targeted and her TV news experience as significantly lacking. CBS News has denied any political interference.

Ahead of his first broadcast, Dokoupil made a litany of public promises. He vowed to be more transparent than Cronkite, to prioritize viewers over the network’s corporate owners and to listen to everyday Americans over academics and elites.

“I think all journalism has a trust problem,” Dokoupil told The Wall Street Journal. “If we’re the yogurt industry, and 70% of people didn’t trust yogurt, it would be a crisis. I think it’s a crisis for journalism.”

In Dokoupil’s first months on the job, the show’s gaffes have been memorialized in news reports. Weiss’s CBS overhaul has thrust him to the center of the network’s tumult, which has played out against the backdrop of Paramount’s deal to acquire rival media company Warner Bros. Discovery.

The merger, which the Justice Department cleared this month, would also place CNN under the control of Paramount CEO David Ellison, whose father is a close ally of President Trump. It has stoked concerns from CBS staffers and media observers about the role American politics is playing in the industry’s era of mass consolidation.

Dokoupil insists there are no tea leaves to read, at least as far as his program is concerned.

“When it comes to Bari Weiss, she’s the editor in chief, she runs a 9 a.m. meeting and has lots of ideas,” he said. “When we like the idea, we use it. If we don’t and if it doesn’t work for our show, we don’t.”

Likewise, he said, “I’ve never met David Ellison. He’s never had a comment about my show. He’s never called me to complain about coverage. If he tried to, it wouldn’t have an impact.”

Growing Pains

Dokoupil’s first day in the anchor chair was in early January, about a month after his dinner with Weiss. The growing pains of his quick transition have been quite public.

“First day, big problems here,” he told millions of viewers during a broadcast when the story teased on-screen didn’t match the text on his teleprompter. Weiss was hands-on during the launch, and with others she had made changes to the script at the last minute, people familiar with the matter said.

Soon after, Dokoupil playfully discussed a series of AI-generated memes depicting Secretary of State Marco Rubio in different jobs, including the Michelin Man and the manager of Manchester United. The images referenced the numerous titles Rubio had taken on in the Trump administration.

“It is a sign of how Florida, once an American punchline, has become a leader on the world stage,” Dokoupil said, referring to the former senator’s home state. “Marco Rubio, we salute you, you’re the ultimate Florida man.”

His comments, perhaps more suited for the levity of a weekday morning show, caught political fire. Dokoupil told The Journal he was making a joke, not trying to be cute about a Trump administration official, but that he wouldn’t do it again.

More recently, the network failed to obtain a visa for Dokoupil to cover the U.S.-China summit. Instead, a last-minute workaround left Dokoupil with little time to pack for a flight to Taiwan on a plane that landed shortly before his show aired. He was also paired with a cameraman—not part of the show’s usual crew—who passed out on set.

“It was a mistake,” Dokoupil said of the visa. “I don’t know. It’s all of our mistake, but someone should’ve got a visa.”

Still, Dokoupil said he was proud of the work he did in Taiwan, where, among other coverage, he spoke with the son of Jimmy Lai, a former tycoon whom a Hong Kong court sentenced in February to 20 years in prison.

“I feel good about what we did, but I’m not going to pretend like it was our first choice.”

The “Evening News” is still a distant third to its competitors, but its May ratings were up 3% year-over-year, according to Nielsen data. In May, the show averaged more than 3.8 million viewers. By comparison, ABC’s “World News Tonight” averaged 8.1 million viewers, up 14%, and NBC’s “Nightly News” brought in 6.1 million, up 7%.

Dokoupil caught the attention of the Free Press, Weiss’s startup, in late 2024. He and his “CBS Mornings” co-hosts were interviewing the author Ta-Nehisi Coates about his book “The Message,” which is critical of Israel. The conversation quickly turned tense when Dokoupil, who converted to Judaism in his 20s, said that the section of the book about Israel “would not be out of place in the backpack of an extremist.”

The interview prompted a conversation in a CBS editorial meeting about bias and objectivity. At the time, the audio from that meeting was leaked to the Free Press, which, like Weiss herself, has consistently defended Israel in its war against Hamas. “How Is CBS Marking October 7? By Admonishing Tony Dokoupil” the outlet headlined a story.

“If I were to do it again, and the moment was the same, I would ask the very same questions,” Dokoupil said.

Weeks before Paramount merged with Ellison’s Skydance in 2025, the company, which was then led by Shari Redstone, agreed to pay $16 million to settle a lawsuit with President Trump over the editing of a “60 Minutes” interview with Kamala Harris.

Weiss’s takeover of CBS News and her editorial decision-making have led to spats with the network’s top talent that have spilled into public view.

The network recently parted ways with Sharyn Alfonsi, a “60 Minutes” correspondent who, in December, accused Weiss of holding a segment critical of the Trump administration for political reasons. Weiss countered that the piece needed additional reporting; the segment eventually ran with some additional material bookending it. Cecilia Vega, another “60 Minutes” correspondent, and the show’s executive producer were also let go in May. And after network veteran Scott Pelley accused Weiss of “murdering” “60 Minutes” in a recent meeting, he was fired.

Pelley and Vega also accused management of making editorial decisions for political reasons, which a CBS spokesman denied.

“What’s being called ‘editorial interference’ is in reality the job description of an editor in chief,” Weiss said.

“When they make comments like that, I pay attention,” Dokoupil said of his colleagues. “But I can only speak for what’s happening on this side of the street, and it’s not the experience that I’ve had.”

What some employees view as a cozy relationship between the Ellison family and the Trump administration has fanned the flames of internal dissent. David Ellison hosted a dinner “honoring the Trump White House” in April, which Weiss also attended. Dokoupil was invited, but declined.

Man of the People

While reporting for his show in Hartford, Conn., known as the “insurance capital of the world,” Dokoupil scurries around, approaching strangers with boy-next-door eagerness, asking them how they feel about their health insurance as part of a series on affordability. “I hate it,” one woman tells him.

He believes his background helps him relate to the everyday people he wants to reach, offering this summary: “Parents weren’t married or divorced. There’s a lot of drinking. There’s drugs. You gotta move a lot. You have money, then you don’t have money,” he said. “That’s the stuff of American families.”

Dokoupil grew up mostly in Florida and Maryland, raised by a public school teacher mother and a drug dealer father.

“If you smoked Colombian weed in the 1970s and 1980s, I owe you a thank-you card,” Dokoupil wrote in his memoir, referencing the tons of marijuana he said his father moved during that time. “You paid for my swim lessons, bought me my first baseball glove, and kept me in the best private school in South Florida, alongside President George H.W. Bush’s grandsons, at least for a little while.”

He launched his journalism career at Newsweek, writing unconventional and splashy stories about Forrest Fenn’s treasure and “free sperm donors.”

Dokoupil said he was worried about the job security of writing for news websites when he began his TV career. At one point, he sold an essay to the New Republic on the “drawing of blood” he underwent while converting to Judaism.

“I was a print reporter, making a print reporter salary with no trust fund to fall back on,” he said of the essay, titled “My Adult Circumcision.” “I needed the cash, I needed the publicity and I thought it was a funny essay.”

Back when Dokoupil was trying to land a full-time TV gig while working at MSNBC, his now-wife, journalist Katy Tur, offered him sage wisdom: “Get rid of your corduroy jacket and your glasses look,” he recalls her telling him. “Do a hundred push-ups, put on a black T-shirt, nothing else. And put your hair up real big.”

“I did it,” he said, and ABC reached out. But he sought out CBS: “I think I fit here. Would you hire me?” he asked. “And they did.”

Tur still advises his outfit choices and weighs in on his on-air performance.

“If there’s any whiff of fakery or performance or inauthenticity, my lovely wife will let me know about it,” he said. “And I’ll get back to reality.”

Former colleagues have watched Dokoupil’s rise at CBS from a distance. Some of it didn’t seem very “Tony-like” to Tina Brown, who worked with him earlier in his career. But difficult transitions can make for great stories.

“I think he’ll probably have a wonderful memoir at the end of this period, which he should write,” she said.

Write to Isabella Simonetti at isabella.simonetti@wsj.com