Photo courtesy of CNN

Chris Cillizza might be the only person in America who can have goofy fun talking about Trumpcare, Russian election interference, and the emoluments clause. CNN’s new political analyst and editor at large—long a punching bag for fellow journalists who tend to be less adept at stacking up digital clicks—somehow maintains an affable, enthusiastic obliviousness even as he tosses out apocalyptic scenarios about the state of democracy.

Whether he’s on CNN discussing Medicaid, or chatting with you about baseball, Cillizza comes off like a normal guy, your brother-in-law from the Midwest, the one who actually seems to like you and won’t get mad at you for talking about the Paris climate accord at Thanksgiving. His enthusiasm is almost tangible: Do you like barbeque? He loves barbeque! You live in Cedar Rapids, Iowa? He loves Cedar Rapids, Iowa, and remembers talking to then-candidate Barack Obama there! And that’s the small difference between Cillizza and a normal guy—he knows, loves, and obsesses over politics.

CNN is banking on Cillizza, the nucleus of its new multi-platform brand “The Point,” as a simulacrum of an “everyman” who can reach out across the great American political rift, needling both Democrats and Republicans with relentless hot takes. That would be great, except Cillizza’s analysis—much like cheese curds, the hors d’oeuvres of the everyman he exudes—is delightful, easy-to-eat, yet often problematic upon digestion.

Why do so many journalists think you suck?”

Consequently, Cillizza tends to be a fly trap for criticism about his criticism. The best recent example is the recent Ask Me Anything (AMA) thread Cillizza did on Reddit. The questions were brutal.

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“Hi Chris, I’m curious as to whether or not you feel your approach to journalism can in any way be damaging to the public dialogue,” asked one user. Another chimed in: “Why do you adopt such a shallow writing style that focuses on subjective emotional reactions towards important political events and not on any type of cognitive analysis that could provide further insight into current events?”

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And in a deleted question, later restored, journalist Libby Watson of Fusion asked, “Why do so many journalists think you suck?”

Despite the relentless Reddit critiques on everything from journalistic ethics to Cillizza’s supposed foot fetish (more later), Cillizza’s responses were upbeat. Unconcerned positivity and genuine zeal are part of the Cillizza brand. In responding to Watson, the critical journalist, he noted, “I would first say that everyone—even reporters—is entitled to their opinion about my work. If that opinion is that it’s terrible, so be it!”

It’s the shruggy emoji of responses—acknowledging criticism, but also noting he has fans. Big fans. Fans who have helped Cillizza, 41, go from a failed novelist and intern for the conservative columnist George Will, to a coveted, high-profile role at CNN. Love him or hate him, people read him: Cillizza’s Reddit AMA attracted more than 100,000 views and 800 questions, making it a top performer for the year.

It’s the Cillizza Catch-22: Amid all the criticism, his traffic stats are unimpeachable. Cillizza is relentlessly popular with mainstream audiences. According to data shared with CJR by CNN, in the first three months of his new job, Cillizza’s most trafficked column (“Donald Trump Just Held the Weirdest Cabinet Meeting Ever”) drew over three million unique visitors. His other most popular columns hold steady at between one and two million unique visitors. Those are big numbers even for an operation that drew 105 million unique visitors in June.

His newsletter, The Point, already is CNN’s second largest after adding 10,000 new subscribers in the first two weeks of July (CNN would not say how many total subscribers it has amassed).

***

BORN AND RAISED in Connecticut, Cillizza’s father taught elementary school and mother worked in human resources for an insurance company. In high school, he attended the elite Loomis Chaffee college preparatory school alongside future professional hockey player Andrew Berenzweig and MTV veejay Jesse Camp. After graduating in 1994, Cillizza studied at Georgetown University as an English major, writing short stories and dreaming of becoming a novelist.

In his sophomore year at Georgetown, Cillizza was recommended by the dean of the college of arts and sciences for a coveted internship with Pulitzer-prize winning columnist George Will. At the time, Cillizza wasn’t interested in politics. He knew about George Will because of his writing about baseball. Will is a Chicago Cubs fan who authored the book Men at Work: The Craft of Baseball.

As an intern, Cillizza learned about civics, statecraft, research, and the political act of car parking. Will drove a Ford Mustang convertible and would drive the car up to the office so one of the college interns could park it for him.

By the time he graduated from college in 1998, Cillizza’s career as a novelist was going nowhere. “If you’ve never published anything,” Cillizza quipped in an interview with CJR, “it’s hard to be a novelist.”

He briefly considered a career as a sports writer, but after a friend interned at CBS, he decided sports would be less fun as a job. Besides, sports and politics have a lot in common—history, personalities, numbers, unpredictability. In the way he collected baseball cards as a kid and poured over stats, Cillizza began pouring over the history of politics.

Through Will, Cillizza heard that political reporting legend Charlie Cook needed some help at his newsletter. So he interviewed with Cook and a got a job as a political reporter. Cook’s favorite “everyman” story about Cillizza comes from the job offer itself, which came with a stipend for parking. Cillizza misunderstood the offer and thought he was being offered a chance to get paid to park Cook’s car.

Cillizza said eagerly, “Great. I used to park Mr. Will’s car.”

“No, Chris,” Cook responded, as Cillizza recalls. “We pay you for parking your own car.”

***

CILLIZZA LANDED at The Cook Political Report in 1998, just as the Monica Lewinsky scandal was erupting into a full-blown frenzy. Then there was impeachment, the 2000 presidential race, the Florida recount, and September 11. It was a trial by political fire, and Cillizza met each story with relentless energy. The Cook Political Report, owned by Charlie Cook, shared an office with the National Journal empire, owned by David Bradley, which encompassed The Hotline and eventually, The Atlantic. The Washington, DC building hosted a group of young reporters on the cusp of their careers—Eliza Newlin Camey, Louis Jacobson, Siobhan Gorman, Shawn Zeller, Amy Walter, Mark Murray, and Chuck Todd. When they weren’t working they were drinking together or playing softball.

Cilliza has never been interested in appearing at fancy parties or rubbing elbows with DC’s elite. Instead, he plays pickup basketball twice a week, and he met his wife, Gia, on the softball field. Cillizza recruited her for his team because the former scholarship field-hockey player at Miami University has a competitive streak.

In addition to his wife, Cillizza met many of his lifelong friends over softball. Lou Jacobson recalls taking dancing lessons with his fiancee and Cillizza and Gia. Cillizza was not a good dancer. “At least he was better than me,” joked Jacobson. Cillizza and Amy Walter sang the 1995 Rob Base and DJ EZ Rock pop hit, “It Takes Two” at each other’s weddings.

Whether he was working on a story about Dwayne “The Rock” Johnson at a Rock the Vote rally or a detailed look at redistricting, “he always wanted to talk to everyone,” recalls Walter, who sat near Cillizza while he worked at The Cook Political Report and often worked on stories with him.

Cook recalls that Cillizza was always motivated by his enthusiasm and his love for people. It was also in these early years that Cillizza showed a gut-level aptitude for the hustle. Even before the web was a regular staple in political reporting, Walter notes that Cillizza was always following up with sources to let them know when and where his stories had been published—promoting himself and his work in a way Walter remembers as evidence of an early acumen for building a brand.

Cillizza himself describes his enthusiasm as the “zeal of the converted.” He considers himself a disciple of the Richard Ben Cramer style of political reporting, which he defines as looking beyond the politics and into what makes the people in politics who they are. In 2010, Cillizza was able to meet Cramer, a legendary political journalist and author of the book What it Takes, a 1,000-plus page look at the 1988 presidential race, who was living in Maryland. Jack Bohrer, who worked for Cramer at the time and is now the author of The Revolution of Robert Kennedy: From Power to Protest After JFK, got together a group of young Cramer devotees—Sasha Issenberg, Jonathan Martin, Ben Smith, and Chris Cillizza—and brought them to Cramer’s home on a political pilgrimage.

Writing in his book, The Gospel According to the Fix: An Insiders Guide to a Less Than Holy World of Politics, Cillizza notes that John Harris of Politico called the visit the equivalent of a young Bob Dylan going to visit Woody Guthrie. Cillizza went back afterward and formed a friendship with Cramer that lasted until Cramer’s death in 2013. For Cillizza, Cramer’s work, and their friendship, forged his identity as a writer, noting for his generation of political reporters, Cramer’s What it Takes “spoke to something elemental about why were were drawn to the field. It tried like hell to get who these people, who were arrogant enough to believe they among all others in the country should represent us in the White House, were before they ever became bold-faced names.”

That interweaving of personality and politics is now a hallmark of Cillizza’s style of writing, which often makes it hard to separate the pundit from the person. Eschewing the dry, formal style of many of his mentors, Cillizza wrote about Ron Paul through the lens of his favorite TV show, Friday Night Lights, noting, “Both Paul and ‘Friday Night Lights’ have in­cred­ibly deep but not all that wide bases of support.”

In a paragraph emblematic of Cillizza’s style, he wrote about Ted Cruz’s endorsement of Donald Trump in 2016:

Ted Cruz called Donald Trump a “serial philander.” He called him a “pathological liar.” He warned the real estate mogul to leave his wife “the hell alone.” And then, on Friday, Cruz endorsed Trump’s presidential candidacy. Er, what?

John Harris, editor in chief of Politico and a Cillizza mentor, notes that while Cramer and Cillizza both saw stories in that intersection of character and politics, Cillizza’s writing is “of the moment. So in that sense they are different. But the spirit is similar and perhaps as Chris’ career will develop into something more long-form in the future.”

***

AFTER COVERING CAMPAIGN POLITICS at the presidential and congressional level for three years, Cillizza in 2005 became Roll Call’s White House correspondent. By then, his fervent energy and penchant for breaking news was getting noticed.

Harris, who was national politics editor at The Washington Post in 2005, remembers being aware of Cillizza because Cillizza was always breaking stories before his team. “When the competition breaks a story, you usually say, ‘That’s no big deal.’ ‘We had that.’ Or ‘That’s not that interesting,’” says Harris. “But sometimes, you say, ‘Dammit! We just got beat.’ And Chris was producing those ‘Dammit!’ stories.”

Harris interviewed Cillizza and was impressed by his unique combination of gravity and entertainment. “Chris is a combination between being a serious student of politics with a level of depth and perception that is uncommon. All that, combined with fun. He can talk about a serious subject in a fun way.”

The most recent example of Cillizza’s “fun” and/or exasperating writing style was his use of a smiley face emojis, when assessing the Republican healthcare alternative to the Affordable Care Act.

“Which brings me to a new feature I am going to do every day between now and whenever we get a Senate vote on the health care bill: An emoji-based assessment of the chances of the health care legislation passing,” he wrote for CNN. “There are three options: 1) Smiley face (good chance of passage) 2) Meh face (50-50-ish chance) and 3) Sad face (less than 50% chance). Every day I’ll write a post with an emoji update of the bill’s chances.”

This attempt at light-hearted analysis of a bill that could have made millions lose their healthcare (if it passed, that was a smiley face) was savaged on Twitter.

Ben Dreyfuss, senior editor at Mother Jones, and others took to Twitter to call Cillizza out.

So, Chris Cilliza has a new feature where the sad face emoji means "people live" https://t.co/IViynQ9OtB pic.twitter.com/NVx7cMrluB — Ben Dreyfuss (@bendreyfuss) June 27, 2017

somebody stop Chris Cillizza. please dear god just make it stop. pic.twitter.com/xVbslpziPf — Mac McCann (@MacMcCannTX) July 14, 2017

Of course, Cillizza was having fun with politics long before the smiley-face emojis. He was known at the Post for distilling a week’s worth of political news into a “winners and losers” column, and quick, cheese curd-sized analysis on who had the worst week in Washington.

In Cillizza, Harris recognized a someone who could make politics palatable, and in 2005 he hired Cillizza to start a blog for the Post. With this move, Cillizza became the first person on the inside of political journalism to make the web his full-time home. At the time, Blogger had been around for six years and and WordPress for two. Matt Drudge was online, of course, and so was Andrew Sullivan, Instapundit, and Red State. Ana Marie Cox founded Wonkette in 2004, the same year Jessica Valenti founded Feministing. And Gawker had been around since 2003. Daily Kos was founded in 2002.

But Cillizza was the institutional inside man and so, as he put it, he “bought up real estate in a place nobody else wanted.” An early web gentrifier, Cillizza tried to persuade colleagues to participate. They scoffed, so it was solo Cillizza writing his now-standard rapid-fire, voicy, political analysis on a blog he eventually called “The Fix.”

The Post didn’t use metrics at first, and Cillizza believes if they did, he probably wouldn’t have lasted long. But that lack of pressure allowed him to experiment with his voice, style, and approach. A brand was born.

I have made mistakes. I have tweeted dumb things. I have said dumb things on television. I will again say something dumb.”

Not all of Cillizza’s friends were fans of what he was doing. Louis Jacobsen, a senior correspondent for PolitiFact, remembers being skeptical about Cillizza’s move to the web, thinking he had taken a step down from his job at Roll Call, and worried about all the contests he was running on the site to drum up readers. Cook, taken aback at Cillizza’s informal style, told him to ask himself, “What would David Broder do?”

In hindsight, Cook is glad Cillizza ignored his advice. “The world has changed, and political journalism has changed,” Cook says in an interview with CJR. “Now I think he’s in exactly the right place and coming across in a serious but enthusiastic way.”

Cillizza barrelled forward despite the skepticism of his colleagues, making himself indispensable to the Post. Reporter David Fahrenthold notes that so many of the things that are now considered basics of political reporting at the Post—quick takes, aggregation, linking out, social media promotion—started with Cillizza.

When Harris founded Politico, he tried to lure Cillizza away from the Post to work for him. Cillizza ultimately refused, a decision Harris chalks up to Cillizza’s wife, Gia, a former college field hockey coach, who he describes as a keen appraiser of the Washington scene.

Harris ended up hiring Ben Smith, who is now editor in chief at BuzzFeed. Harris laughs imagining an alternate political journalism reality where Cillizza had become an editor at Politico. But he ultimately agrees Cillizza made the right call.

After he began at The Washington Post, Cillizza’s profile and brand began to grow, and so did criticism of his work. In 2009, The Washington Post canceled his comedy series “Mouthpiece Theater” when he and co-host Dana Milbank suggested in a segment that Hillary Clinton should drink “Mad Bitch Beer.”

Jay Rosen, media critic and professor of journalism at New York University, is a relentless critic of Cillizza’s informal style of political punditry. He believe’s Cillizza’s work weakens the country’s trust in journalism.

In 2014, Rosen described Cillizza’s emphasis on “savvy” journalism as a mistake. He warned that the quick-infotainment approach to politics would turn analysis into gamesmanship, cultivating a class of people who were just into politics for the fun, rather than assessing real-world implications. Rosen explained, “The savvy severs any lingering solidarity between journalists as the providers of information, and voters as decision-makers in need of it.”

You could put a cactus in my job and people would criticize the cactus.”

The social media back and forth between Rosen and Cillizza got heated and eventually, Cillizza blocked Rosen on Twitter. He’s since unblocked him and reached out to Rosen to collaborate on a story. Rosen tells CJR in an email that he cooperated with Cillizza as a means to get his message out.

Other prominent critics of Cillizza did not respond to interview requests. Liz Spayd, former public editor for The New York Times, was managing editor for national news at The Post during the “Mad Bitch Beer” incident and said at the time that Millbank and Cillizza had “crossed the line.” Spayd declined to comment about working with him, but noted, “Chris was a creature of the web far ahead of his peers at The Post. He understood that the battle for readers wasn’t going to be fought on the front pages of newspapers.”

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The fight for audience has brought Cillizza to some ugly blows on social media with his colleagues in the world of political reporting.

Cillizza says criticism of his work isn’t unique to him, but just another facet of political reporting. “You could put a cactus in my job and people would criticize the cactus,” he says.

As Sam Feist, a CNN senior vice president and Washington bureau chief, noted in an interview, “Chris writes five times a day. There is a lot of Chris Cillizza to talk about, to agree with, or disagree with.”

A few highlights (or lowlights, depending on who you ask):.

He wrote a second-by-second analysis of a handshake between Trump and French president Emmanuel Macron.

In a piece on a weird Trump cabinet meeting, Cillizza wrote:

Donald Trump did something very different in his Cabinet meeting Monday. First, he reviewed the various alleged successes of his first 143 days and made this remarkable claim: “Never has there been a president….with few exceptions…who’s passed more legislation, who’s done more things than I have.” Um, ok. While Trump has signed a number of executive orders and actions — the most high profile of which, the so-called “travel ban” was, again, blocked by a court on Monday — what he hasn’t really done is pass actual legislation through Congress. The health care bill is tied up in Senate machinations. Tax reform hasn’t moved an inch. Funding for the border wall hasn’t happened.

In an article on Trump’s battle with Jeff Sessions he wrote:

“We love this job,” Sessions, seemingly unbowed by Trump’s smackdown, said. “We love this department, and I plan to continue to do so as long as that is appropriate.” Um, ok. As if being called out by your boss, who also happens to be the President of the United States, isn’t bad enough for a week, Sessions took another gut punch on Friday night.

Writing in defense of Ivanka Trump, he explained:

You can hate Donald Trump’s views on and treatment of women — and lots of people do! But, to expect Ivanka Trump to publicly condemn her father or his record on women’s issues is a bridge too far. It’s impossible for us to know what Ivanka Trump does (or doesn’t do) to influence her father’s views behind the scenes. And, because of that — and the fact that she is his daughter! — booing her for defending her dad is poor form.

Oh, and about that shoe fetish. Only weeks on his new job, Cillizza tweeted a picture of CNN Chief Political Reporter Dana Bash’s choice of footwear.



Responses to the tweet accused Cillizza of voyeurism and worse.

There have been other social media dustups, too. Recently, journalist Olivia Nuzzi of New York magazine called Cillizza out for his analysis that Joe Scarborough might be running for office.

As the author of the story, let me just say: no, he isn't. https://t.co/GJtNUGb2fY — Olivia Nuzzi (@Olivianuzzi) July 25, 2017

When reached for comment, Nuzzi simply replied via email, “In the words of Sean Spicer, my tweets speak for themselves.”

In response to all of this criticism, Cillizza tells CJR, “I’ve never tried to portray myself as someone who is not human. I have made mistakes. I have tweeted dumb things. I have said dumb things on television. I will again say something dumb.”

But Rosen is not so easily swayed by Cillizza’s “meh” response. “I think Chris would be smart to reflect on why so many people who follow political news closely are so frustrated with him,” Rosen writes in an email to CJR. “Maybe ‘I’m independent, I call it the way I see it, and that means clashing with partisans who see only virtue in their side,’ which is the kind of answer he would probably give, doesn’t fully explain it. He should treat this as a mystery he is going to resolve.”

Cillizza admits the criticism does get under his skin at times. But he finds relief offline—playing pickup basketball, going over sports stats with his two young sons who are already fervent Nationals fans, and dining out with his wife.

The key, he believes, is learning to separate the noise of the internet with legitimate criticisms. “If I said, ‘The sky is blue’ people would be like, ‘Typical Cillizza!’ But there are people who are critical and sometimes harshly critical, but in a way that’s worth listening to, I think.”

Cillizza engages with his critics with his signature brand of Cillizza fun. When someone on Twitter made fun of his hiring at CNN, writing, “gonna pay someone to hit me in the head with a brick and then just wait to be offered a six-figure media talker job.” Cillizza replied that he was actually earning eight figures.

Try 8 figures https://t.co/Vl9ZoWWI35 — Chris Cillizza (@CillizzaCNN) May 24, 2017

The joke, as it were, took off. And provoked even more backlash. On Reddit, Cillizza acknowledged he definitely does not make eight figures. But the ire the joke drew highlights the tension between Cillizza and the world of media.

Despite the unintended consequences, Cillizza continues to face his critics, valuing a radical transparency that he describes as “showing his work.” After Norm Ornstein, resident scholar at the American Enterprise Institute and a contributing editor at The Atlantic called Cillizza’s journalism “pathetic,” Cillizza reached out to him and they had a back and forth that was eventually published on “The Fix.”

They never reached a resolution, but Cillizza shrugs it off: “You don’t have to please people all the time.”

And who is he trying to please? Well, it isn’t journalists. In a column in The Washington Post, Erik Wemple wrote that Cillizza is playing the long game, growing a mainstream audience and building a perception he’s a regular guy kind of political reporter and not a media insider—an analyst who can appeal to both sides of a divided nation.

A representative of CNN took Wemple’s article as serious and indicative of Cillizza’s focus. I almost took the article as serious, too, until I looked closer. How do you know the article is parody? It’s a list, written exuberantly, and the links poke fun at Cillizza’s own comments.

It’s the perfect example of being Cillizza’d—that thing when you can’t tell where the serious analysis ends and the jokes begin.

Cillizza does come off as an everyman. Talking about BBQ and baseball in our interview, the only thing that was omitted was apple pie. Walter notes that the Cillizza you see on TV is the same Cillizza who sits across from you at a table—same enthusiastic hand gestures and asides. Yet, this everyman appeal might on the surface be idiosyncratic for his new audience— Cillizza, after all, sports an elite education resume (he’s jokingly called his high school the “Loomis Chaffee school for the rich”) and political insider status.

In his work, pandering to both sides is what Cillizza does well. He’s been criticized for his coverage of Clinton’s emails and his defense of Ivanka Trump. And while some media critics like Rosen would say Cillizza’s criticism points to deeper media issues, Feist believes that Cillizza’s divisiveness is indicative of his cross-party appeal. “That’s what a nonpartisan political analyst does,” notes Feist. “He offers analysis and you are criticized by both sides, and I would say generally that’s a good thing.”

Cillizza for his part is trying to move beyond these battles as he moves up. He tells CJR he’s not interested in toxic social media battles, and since moving to CNN, he’s unblocked all his critics on Twitter.

Instead, he’s focusing on the current moment. “My job is not to know the future. My job is to say, ‘Here is what we know about where we are what that would suggest based on prior knowledge, based on reporting.’ And when that’s wrong, say, ‘Here is what we got wrong.’”

And as he tries to direct his political coverage into the void of American political dissonance, Cillizza does so with his trademark enthusiasm, transparency, and sports metaphors. Noting that he can be nothing more than himself. “When I was younger, I would sit down to write something and be like, ‘Okay, I have to be serious now. This is serious.’ And politics is serious, but there is also the sublime in politics. You have to recognize the ridiculous. They go hand in hand. Often second by second.”

With this mix of serious and sublime, Cillizza is holding his own at CNN. And his power to command an audience, whatever they may think, continues to grow. Cillizza’s new brand currently encompasses an email newsletter, and a several-times-a-day column, with much more to come.

And if he makes another mistake? Well, as Harris tells CJR, “When you hire Chris Cillizza, you know what you are getting: Chris Cillizza.”

Correction: This story has been updated to reflect the correct spelling of Dana Milbank.

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Lyz Lenz is a writer based in Iowa. Her writing has appeared in Pacific Standard, Marie Claire, Jezebel, and the Washington Post. Follow her on Twitter @lyzl.