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How Soledad O’Brien Became CNN and the Mainstream Media’s Most Outspoken Critic

The former CNN host turned CEO and film producer sounds off to Lloyd Grove about why the cable news media’s been such an embarrassment during the Trump era.

Lloyd GroveNov. 18, 2019 4:44 AM ET

For Soledad O’Brien, the presidency of Donald Trump has ripped the cover off a lot of things, including the fragility of American democracy, the cravenness of many of our elected officials, and—most urgent for O’Brien—the soft and vulnerable underbelly of U.S. journalism.

“Poor journalism does drive me crazy. It does make me lose my mind,” O’Brien told The Daily Beast as her latest project, Hungry to Learn, was premiering at the DOC NYC documentary film festival.

It’s a feature-length exploration of the little-known yet pervasive phenomenon of financially strapped college kids facing food insecurity; after paying for tuition, housing and textbooks, they don’t have enough money for regular meals, with debilitating consequences.

But first: O’Brien’s sharp insights on journalism in the Trump era.

“What drives me more nutty than the president—who I think is obviously a terrible human being in a lot of ways—is the way in which the media does not know how to handle him,” she said. “Quoting people who are saying lies is a really bad strategy. When President Trump says the moon is made of cheese, well, it’s not,” she continued, speaking metaphorically.

“What drives me really crazy is to see all the mistakes the media makes around [the problem of], how do you report on somebody who’s a liar, who won’t hold press conferences in a place where you can ask real questions?” O’Brien continued. “How do you use your access? Every so often, someone writes a story about Ivanka that sounds like it’s been written by Ivanka. And you can tell that this is the access piece, so you can get that little drip, drip, drip that she’s giving.”

O’Brien, who identifies as black and Latina as the daughter of an Afro-Cuban mother and Australian-Irish father, is especially troubled by what she sees as the mainstream media’s tendency to soft-pedal toxic rhetoric emanating from the White House and Trump’s followers in Congress and elsewhere.

“As a woman of color,” she said, “you sit there and think, this shit is just racist, and I’m disappointed when journalists have a really hard time in just saying ‘this thing is a lie, this thing is racist, this thing is bigoted, this thing is misogynistic.’ It’s not super-complicated.”

O’Brien added: “The idea of something being ‘racially charged’ or ‘racially tinged’—what the fuck is that? Journalists will bend over and literally do gymnastics to avoid calling someone a racist. Or ‘verifiably untrue.’ It’s just a lie! What is wrong with you? That actually drives me insane. It’s just a failure of journalism.”

Shortly before the election, for instance, O’Brien was incensed when Mother Jones magazine published an article about neo-Nazi Richard Spencer that politely described Spencer as “an articulate and well-dressed former football player with prom-king good looks” and “the alt-right’s outlaw version of William F. Buckley.” 

“Remember when Mother Jones did the whole Richard Spencer ‘he’s so dapper’ story?” O’Brien said. “This whole idea of, like, they’re racists but they’re so lovely. Or they might be racially tinged, but they’re so alt-right.”

At 53, after three decades in the television-news business as a high-profile anchor on MSNBC, NBC and CNN, and for the past six years the self-styled “boss lady” of her own production company, the Starfish Media Group, O’Brien has taken on the public role of media critic.

Although she offers her blunt and occasionally brutal assessments mainly on Twitter, where she boasts 1.1 million followers, it’s clear she approaches this venture not as a mere hobby, but with the fiery passion of an avenging angel.

“One of the nicest things about being in your fifties is I don’t need any more friends,” she said. “I think it is more important to credit people when they do a good job and ask a good question and call them out on their bullshit when they do a bad job.”

One of the nicest things about being in your 50s is I don’t need any more friends. I think it is more important to credit people when they do a good job and ask a good question and call them out on their bullshit when they do a bad job.

Her targets include her former employer CNN, especially politics reporter and editor-at-large Chris Cillizza; NBC News’ Chuck Todd, the moderator of Meet the Press—whom she compares unfavorably to Fox News’ Chris Wallace—and MSNBC’s Joe Scarborough and Mika Brzezinski.

“I’m never going to be friends with Joe Scarborough. That’s OK. That’s not happening. And I’m sure he doesn’t want to be friends with me,” O’Brien said with a laugh. Despite their generally fierce criticism of Trump over the past three years, “I think Joe and Mika have a short memory about how much they had President Trump on and were his besties when he was running for office,” O’Brien said. “And it was all a big joke. I don’t think that’s mean, I think it’s just honest about people’s roles.”

On a recent podcast, O’Brien was even more pointed in her scolding of the married Morning Joe duo. “They’re tiresome,” she told interviewer Michael Golden. “He and Mika had Trump on their show dialing in, all laughing, going to give him advice and consulting with him. I mean, come on! Give it a break!… It’s a little too precious and a little too exhausting. Also, where are they? I think they live in Florida now. But they’re never actually on their show. It’s the weirdest thing. I thought ‘tiresome’ was a good word because they’re just a waste of time, honestly.”

Scarborough, Brzezinski and MSNBC—which recently celebrated a record-breaking October for the 6-9 a.m. program, with an average of 1.23 million viewers—declined to comment on O’Brien’s broadside.

Chuck Todd—who likewise declined to comment—is also a recurring subject of O’Brien’s Twitter feed.

“Why is Chuck Todd grinning and laughing through an interview that is at it’s [sic] core about disrespecting a military family with a long legacy of service?” O’Brien tweeted in June about a Meet the Press episode in which acting White House Chief of Staff Mick Mulvaney defended hiding the Navy destroyer USS John S. McCain, docked in Japan, from a visiting President Trump so as not to annoy him. “This is so utterly inappropriate and lame.”

“He never follows up. It’s a hallmark,” she complained in July.

“When you’ve lost Chuck Todd, it literally means nothing,” O’Brien tweeted later in July—a retort to Trump acolyte Steve Cortes’s remark, “When you’ve lost Chuck Todd…,” referring to the NBC News anchor’s assessment of Robert Mueller’s halting congressional testimony: “On optics, this was a disaster” for Democrats.

On the other hand, O’Brien praised Todd’s more recent contentious interview with Wisconsin Republican Sen. Ron Johnson, who insisted on spinning conspiracy theories until Todd cut him off and forced him to answer why he “winced” at Trump’s notorious phone call with Ukraine’s president: “This was very strong from @chucktodd,” she tweeted. “Young journos—this is how to press. Respectful, but it’s your show. Hold your guests accountable and keep them on track.”

Perhaps surprisingly, O’Brien saves her most effusive endorsement for a Fox News anchor. “Chris Wallace is not afraid of his guests. Chris Wallace is a very tough interviewer,” she told The Daily Beast. “And you can see that he views his show as his turf. You cannot come onto his turf with some kinda bullshit.”

As for CNN—where O’Brien spent a decade as a morning anchor and the creator of prime-time documentary specials such as Black in America and Latino in America—“it’s really problematic,” she said.

“How can they put Kellyanne Conway on as a badass woman?”—a reference to Washington correspondent Dana Bash’s sympathetic profile of the top White House adviser. “Literally, she’s got all these Hatch Act violations, and she’s clearly lying when she comes on TV. Listen, when people lie, they shouldn’t be invited back—on the left or the right.”

Citing CNN’s recent hiring of pro-Trump former Republican congressman Sean Duffy (“who doesn’t know shit about anything… Why is he weighing in?”), O’Brien is especially critical of the cable network’s “strategy to create drama and conflict,” as she described it, “by putting people on who are willing to say despicable things. I get it. And it’s cheap. It costs little money. All the people who are talking heads are paid a salary for the year and you just rotate them through show after show.”

O’Brien has repeatedly attacked CNN’s Cillizza, meanwhile, for breezily treating the Trump administration as an entertaining spectacle rather than exploring its substantive, serious impact on real people—as with a March 2018 column headlined: “Donald Trump is producing the greatest reality show ever.”

“This terrible analysis by @ CillizzaCNN is in part why people hate the media,” O’Brien tweeted. “It’s not accurate. It’s not funny. It’s not clever. It’s not analysis. It’s facile,” she added. “It shows an actual lack of understanding of reality tv (can’t believe I’m typing that). It’s mediocre. It’s a time when viewers need to understand what’s going on at the highest levels of govt.”

Cillizza didn’t respond to an email requesting comment. A CNN spokesperson, however, fired back: “Soledad is certainly entitled to her opinion. But let’s acknowledge that she’s become more of a liberal activist than a journalist. Slinging insults on Twitter is easy. Reporting on the President and understanding the complexities, perspectives and personalities driving his administration and supporters is much more important, and also more difficult.” 

Harvard graduate O’Brien might be politically liberal, but she’s also an accomplished broadcast journalist. She’s a regular contributor to PBS, the host of Hearst Television’s nationally syndicated public affairs show, Matter of Fact, a correspondent for HBO’s Real Sports with Bryant Gumbel, and the recipient of two Peabody awards and other prestigious laurels over a career that has ultimately led her—after CNN Worldwide President Jeff Zucker didn’t retain her as an on-air personality—to forming her own for-profit Manhattan-based media company that employs a dozen full-time staffers.

With her husband Brad Raymond, an investment banker, O’Brien also runs the charitable PowHERful Foundation, which has raised more than $5 million, she said, toward sending girls to college.

Hungry to Learn—for which O’Brien is executive producer and secured grants from the ConAgra and William T. Grant foundations to the tune of around $500,000—is her seventh independent documentary. Over a period of more than two years, it tracks the struggles of four college students from families that can’t help them financially as they try to meet their academic obligations while taking onerous loans and working at off-campus jobs—frequently facing the cruel choice of either eating or paying their semester fees.

At the recent premiere, where two of the spotlighted students spoke about their experiences to a full house at New York’s SVA Theater, O’Brien explained why she was drawn to the subject. “There are so many students” facing food insecurity, “but there’s so much shame and embarrassment,” she said. “I think it really was the data…We had originally thought it was a handful who are struggling, and then you realize, oh my goodness! It’s not a handful. It’s actually a massive number. And so we were very interested in exploring where that number is coming from. Then we could start exploring this issue that was just a data-point. How many students are hungry on campus?”

It’s the sort of in-depth journalism that O’Brien wishes were more the norm than the exception in the Age of Trump.

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