If you’re someone who’s been unlucky enough to get fired from a job — whether it was for cause or the result of mass layoffs — there’s a good chance you remember it as one of the worst days of your life. The experience brings with it such a potent mix of shame, insecurity, and anxiety that it triggers a feeling almost akin to shell shock. 

Chris Cillizza certainly experienced all of those emotions when he was let go from CNN in December of 2022, but he has the added bonus of getting to relive them whenever someone wants to be cruel to him on the internet. On October 3rd, for instance, a Twitter account with the username Brady Eyestone tweeted a reply that read, “Jesus man. This is why CNN fired you.” A few days before that, another user named Sann Diamond tweeted, “There's a reason why CNN fired you.” In fact, if you run a Twitter advanced search for the terms “@ChrisCillizza,” “cnn,” and “fired,” you’ll see that someone lodges this attack roughly every other day, on average. In September alone, 17 tweets contained those three words.

Cillizza has developed a thick skin after so many years of writing about politics on the internet, but it’s clear that this particular brand of insult gets to him, especially because he thinks it mischaracterizes his firing. “As far as I know, I was a number on a spreadsheet for a company that we knew needed to cut money,” he told me. During his entire tenure at the network, he had received nothing but positive feedback from his bosses, and his pieces were a major traffic driver for CNN’s website.

Cillizza also doesn’t understand why someone would celebrate such a uniquely horrible event, even if it happened to someone they didn’t like. “About 40% of people who work will be laid off at some point in their life. So it's not 90%, but it's also not 5%,” he said. “It fucking sucked. It was awful … Let's say a person I really don't like in politics gets laid off. I could never imagine being like, ‘hey, man, still unemployed?’ It’s a weird flex.”

But whatever pain Cillizza feels from these cheap shots is at least partially assuaged by the progress he’s made in his post-CNN career. In early 2023 he soft-launched a Substack publication that, as of this writing, has reached 3,654 paying subscribers, which translates roughly to $200,000 in annual revenue. His YouTube channel has grown to over 46,000 subscribers and its videos regularly amass tens of thousands of views — not exactly MrBeast numbers, but also not that far off from the viewership for your average CNN segment. And in November he’ll begin hosting a weekly TV series for the Monumental Sports Network where, per Washingtonian, “he’ll interview politicians and politics-adjacent people about their own athletic experiences and fandom.”  

This is the kind of success most independent content creators only dream of, but Cillizza readily acknowledges he’s still a far way off from replacing his CNN salary (he once quipped on Twitter that he made “8 figures” but later clarified he was joking). He also doesn’t pretend he didn’t enjoy the prestige of working for such an esteemed news brand. “I liked that people knew me,” he said. “I'm honest enough to admit that to myself. It wasn't just like, oh, I'm doing great journalism. I liked not having to explain where I worked to people I called. And I think that this whole experience has taught me that I liked it too much, to the point where it was not good for me. It was too definitional.”

Now Cillizza is trying to define himself as something else. A creator. An independent journalist. An entrepreneur who built a business that isn’t subjected to the vicissitudes of a media conglomerate that views its employees as numbers on a spreadsheet.

But the question remains: can it ever provide him with the same satisfaction he received from working for the world’s largest news brand? Can a viral YouTube video ever produce the same high as knowing his face was beamed out to every airport and doctor’s office in America? 

That’s a question he still doesn’t know the answer to.

The birth of a politics junkie

Growing up, Cillizza didn’t aspire to become a journalist — nor did he have much interest in politics, really. “I wanted to be a novelist,” he told me. In the late 1990s, he was attending Georgetown University and got a job working for the conservative columnist George Will; as luck would have it, Will's office was in Georgetown and he tended to hire undergrads from the school purely for proximity reasons. “I didn't work for him because I was conservative or liberal or knew anything about politics. I worked for him mostly because he paid like $12.50 an hour, which in the mid 1990s was a king's ransom.”

The job wasn’t particularly sexy. Yes, Cillizza sometimes helped Will with researching his columns and books, but he also stayed at the columnist’s house when he traveled for long stints and handled errands like parking his car. Cillizza must have made some sort of impression, however, because Will recommended him to Charlie Cook, one of the nation’s preeminent political analysts and the founder of The Cook Political Report.

It was there he caught the politics bug. Then as now, The Cook Political Report maintained its competitive edge by providing analysis on little-followed campaigns — the kind for which there isn’t much public polling. While these races don’t attract the same kind of mainstream attention as a presidential campaign, they’re arguably just as important, at least in aggregate. Compiling the report requires a granular understanding of voting trends that isn’t reflected in the commentary from your average cable news pundit.

Cook hired Cillizza to answer the phones, and he simply started learning through osmosis. “Yes, I answered the phones, but the phones didn't ring constantly from 8 a.m. to 5 p.m,” he said. “So a lot of the time I was talking to [the staff] about politics and, eventually, like six months in, I asked whether there was a way that I could kind of get into the editorial side of the business.” Editor-in-chief Amy Walter allowed him to start contributing to reports on the house and governor races, and his interest in politics quickly escalated into an obsession.

Eventually, Cillizza realized he wanted to make the jump to “Capital J, Journalism,” as he put it, so Cook helped him get a job at Roll Call, a twice-weekly print newspaper that was mostly distributed on Capitol Hill (think of it as a sort of proto-Politico). It was there he learned how to write against a daily deadline and break news. In those days, the best way to guarantee a spot on the front page of a Capitol Hill newspaper was to break news of a Senate retirement, so Cillizza focused his efforts on cultivating Senate staffers as sources.

I joked that Cillizza was the politics version of Adrian Wojnarowski — the famed NBA journalist who consistently broke news on major picks and trades — and he laughed. “I still remember all the times when they would publish it, because it was always based on anonymous sources; it would never be a statement from the senator who was retiring, and it was very stressful, which is one of the reasons I got out of breaking news —  because I just couldn't handle the stress.”

The embrace of the “Vegas buffet”

During Cillizza’s entire tenure at Roll Call — which lasted from 2001 to 2006 — the paper operated almost entirely as a print business. Articles often didn’t appear online until after they hit the newsstands. Cillizza kept his focus on getting his byline in the newspaper, but he wasn’t blind to the reality that “the internet as a content vehicle for journalism started to exponentially ramp up” in the mid 2000s. This was the era of the so-called “netroots” — when blogs like Daily Kos and Talking Points Memo and Instapundit generated hundreds of thousands of visits per day. Freed from the confines of a print schedule, these blogs were able to react to the news in real time, which in many ways allowed them to outmaneuver their much bigger mainstream media counterparts.

Eventually, media executives determined that they couldn’t cede entire news cycles to these scrappy bloggers, so they began to erect standalone blogs within their websites in order to keep their homepages fresh throughout the day. Typically, these blogs were staffed with young writers who operated separately from the older veterans, most of whom continued to write around print deadlines. This is how, in late 2006, Cillizza came to be hired by WashingtPost.com to write for its new politics blog.

Now, it’s important to remember that, back then, The Washington Post and WashingtonPost.com were run almost as separate entities, with the latter housing its own staff across the Potomac. As Jim Brady, the former executive editor of the website told the Columbia Journalism Review earlier this year, WashingtonPost.com was “able to experiment like crazy without anybody at the paper being able to say, ‘I’m not comfortable with that,’ because they didn’t know enough to be comfortable or not comfortable. That was really freeing, and it allowed WashingtonPost.com to develop this culture of innovation and ‘Let’s try anything.’”

Cillizza thrived in this independent environment. Originally, his role was pitched as him being a hybrid go-between for the two newsrooms. “I would be someone who would spend like two or three days in the Post newsroom that was, at the time, at 15th and M Street, and I would spend a couple days a week in Arlington in the Post.com newsroom.” The idea was that the veteran reporters would take all the morsels that didn’t fit within their print pieces and feed them to Cillizza to publish on the blog.

This idea proved untenable almost from the get-go. The print reporters didn’t really care about the internet and couldn’t be bothered to collaborate with what they considered a lesser medium. This gave Cillizza lots of free time to write about anything he wanted, and so he began pumping out multiple blog posts a day. Reflecting back on that period, he compared it to investing in undervalued real estate in a burnt-out part of town. “I was buying up houses for cheap because no one else wanted to live there. And then all of a sudden it was like, oh my God, why doesn't everyone live here?”

This was a mostly pre-social media era when the websites that generated the most traffic were usually the ones that posted the most often. In 2007, several Washington Post staffers left to launch Politico, a website that atomized political news into microscoops and really crystalized the idea that the internet was a bottomless well of content where no news was too petty or small to post. Cillizza completely bought into this philosophy. “It was just like, how many swings can you take?”

Meanwhile, Politico didn’t just change the game for how web journalism was done, it also operated on the principle that its reporters needed to own the narrative across all available mediums, and in that era, TV was still dominant. It hired two publicists whose full-time jobs were to develop relationships with cable news producers and pitch Politico journalists to come on to provide analysis on that day’s news.

Up until then, most print reporters considered TV news to be beneath them, but once again Cillizza found himself the beneficiary of these changing norms. In 2008, he started receiving frequent invites to come on cable news shows, including near daily hits with MSNBC’s Andrea Mitchell. This got even easier when the Washington Post built out its own in-house studio so that its reporters could do these hits without leaving the newsroom.

Cillizza discovered he loved doing TV hits as much as he loved blogging. “My basic theory of journalism at that point was that, 50 years ago, if you were hungry, your options were meatloaf, potato, and broccoli. That's what CBS, NBC and ABC served, and that's all you could eat because no one else was serving food.” But by the late 2000s, the media environment was more analogous to a 24-hour Vegas buffet. “You want to get barbecue at two o'clock in the morning? Sure. You want an omelet? Sure. You want ham? Sure. And my view was like, okay, I want to be at as many of these buffet stations as possible. Some people are going to consume me on TV. Some people are going to consume me on podcasts. Some people are going to consume me in the written word. And TV obviously was, and probably still is, the biggest of those buffet stations.”

At some point in 2011 or 2012, Cillizza became a paid MSNBC contributor, which basically meant that he maintained his job at the Post but his TV hits were exclusive to the network. For the most part, his bosses at the Post were fine with this, but sometimes those two roles could come into conflict. “The problem with that was you're a servant of two masters at some level. Like on election night, am I at MSNBC or am I at the Post?” He didn’t like having to choose. 

That was why the CNN offer was so appealing to him. At the 2016 Democratic convention, he sat down with Andrew Morse, then an executive vice president at CNN, and Jeff Zucker, who ran the network. The deal they eventually fleshed out basically took every aspect of his existing career and made it better. CNN had one of the biggest websites in the world in terms of traffic, and, at that point, its TV ratings were still beating MSNBC. “And by the way, it was more money,” he said. “So I would have a bigger platform, more eyeballs, more money. I can do everything I want under one roof.” In March 2017, CNN announced it had hired Cillizza to serve in a dual role that involved both online writing and on-air commentary.

The CNN era and the rise of the Trump #resistance movement

Yet again, Cillizza had timed a career shift perfectly. In normal times, interest in political news waxes and wanes depending on whether it’s an election year, and if Hillary Clinton had won in 2016, then his hiring at CNN would have coincided with a downshift in web traffic and cable news ratings. 

But Clinton didn’t win the election. On the first day of his presidency, Donald Trump stunned the world when he forced his press secretary to take the podium and claim that his boss’s inauguration had been the most-attended in history. The White House immediately became the epicenter of what was arguably the highest-rated reality TV show in existence, and the entire Earth tuned in each day to watch in horror. News organizations started experiencing what they later referred to as the “Trump bump” — massive surges in traffic that spiked every time Trump tweeted from his Oval Office toilet.

Cillizza was the perfect animal to benefit from this Trump bump; he could write copy fast and, because his job entailed political analysis more than original reporting, he could react to the news almost in real time. From his earliest months at the job, according to a CJR profile from 2017, his posts were regularly generating north of 1 million unique visitors each. 

Not all of this attention was positive; in fact, much of it wasn’t. Even before joining CNN, Cillizza has been criticized for having a callous approach to his coverage, one that sidestepped the cruelty and the lies perpetrated by the Republican party and instead treated politics as a game of balls and strikes. The NYU journalism professor Jay Rosen coined the phrase “view from nowhere” to describe this kind of context-free coverage all the way back in 2003, and over the years he’s repeatedly accused Cillizza of being one of its worst practitioners.  

The Trump era brought this sort of criticism to a whole new level. A growing #resistance movement sprouted up and seized on a narrative that the mainstream media had been complicit in Trump’s success. By carrying his rallies live (CNN) or publishing dozens of front-page stories about Hillary Clinton’s private email server (the New York Times), the journalism profession had failed to paint a clear picture of the dangers Trump posed.

And, perhaps more than any other media figure, Cillizza became the punching bag for this sort of criticism, with people being especially vicious on Twitter. 

Want an example? In 2017, a Republican congressional candidate named Greg Gianforte body slammed a Guardian political reporter to the ground and began punching him. A few days later, after Gianforte had already been charged with misdemeanor assault, Cillizza tweeted, “Did you spend a second over Memorial Day weekend thinking of Greg Gianforte's choke slam? Me neither. Which means Republicans bet right.”

The tweet generated 1,300 comments, and most were not kind. The now-infamous Olivia Nuzzi responded simply with, “You are so fucking dumb.” Kate Aurthur, who was then a reporter at Buzzfeed News, asked, “Do you ever regret these tweets that are met with universal mockery?” Writing for Pajiba, Kayleigh Donaldson described Cillizza as being “poisonous milquetoast”:

This is a political journalist, a man whose job is to inform the people and provide a greater understanding of often complex issues, reducing a public assault to a C-List talking point. Essentially, he’s doing the GOP’s job for them, by barely acknowledging there may be a problem with a candidate choke-holding a journalist. There’s no intellect here, nor is there any humanity. For Cillizza, people’s lives are just another sport to bet on. It’s cynicism without the decency to be witty or interesting.

Chris Cillizza wants to view the world as a game, an abstract concept where the stakes have no real consequences, and his continuing efforts to seep politics of that search for truth is simply fake news with a veil of false neutrality.

I of course asked Cillizza about this type of criticism. His response, as I interpreted it, is that he covers politics like a game because it sort of is one. The results of an election are binary; there’s a winner and a loser, and a dispassionate analysis of why each side won or lost has informational value (after all, Gianforte won that congressional election and later went on to become the governor of Montana, despite the almost universal condemnation from liberals and the press). If Democrats want to beat Trump, they need to understand why he appeals to so many Americans. “At a minimum, he's going to get 46% of the vote. So I want to try to understand why … I'm not interested in saying, like, every one of the 74 million people that voted for Donald Trump in 2020 is a racist and an idiot. I just don't think that's true. Are there racists and idiots in his coalition? Sure. But is it 74 million people? No.”

He’s also just unapologetic about what interests him. “The reason that I got into political journalism was not because I was driven by a viewpoint or an issue — like, oh, I really care about the environment and I want to write about the environment. I got into it because I love the history of it, the personalities, the strategy, like that's all the stuff I cared about, and I wanted to be as sort of genuine about that as possible.” Those who aren’t interested in horse race coverage, he argued, have no shortage of other outlets to choose from. “It's not mandatory that you read me … I get there are people who are like, ‘I want to know about education policy, and you're not writing about that.’ I think that's totally fair, and there are places where you can go read that. It's just not me.”

I had a hard time believing that he was completely devoid of political opinions. “Is there anything that Trump does or says that kind of pierces that veil and just horrifies you as a person?” I asked. Cillizza responded that Trump’s actions on January 6th undermined “a basic tenant of our democracy” and that they were “bad and disqualifying,” But at the same time, “it didn't move people when Joe Biden spent months talking about capital D democracy. And so I think part of my job is to grapple with, OK, why not? Like, why do people actually not think that's a big deal?” He doesn’t let his personal feelings get in the way of trying to answer that question.

Regardless of the blowback on Twitter, Cillizza continued to receive high marks from the executives who had hired him. The problem, as he later determined, was that those higher-ups gradually started to disappear. In 2022, CNN’s parent company completed its merger with Discovery, and then a few weeks later Netflix announced its first quarterly loss in subscribers, a revelation that not only sent its own valuation tumbling, but also cratered the stock prices of every publicly-traded media conglomerate, including the freshly-minted Warner Brothers Discovery. CEO David Zaslav had inherited tens of billions of dollars in debt from the merger, and now he faced thousands of increasingly-impatient shareholders who were no longer convinced of streaming’s bright future.

By that point, CNN was already in chaos. Jeff Zucker had been thrown out and replaced with Chris Licht, a former late night producer who came in with a mandate to shake up the network’s programming and wrestle viewership back from Fox News and MSNBC. He promptly shut down CNN+, the company’s $300 million bet on streaming, and began hiring and firing talent at a rapid clip. At some point, it dawned on Cillizza that nobody who had sat in on his initial hiring meeting was still at the company. “So I didn't really have a person high up who was kind of looking out for me.”

Still though, his articles continued to generate great traffic, so he assumed his job was safe. But then in late 2022, roughly a week after Thanksgiving, he received an email asking him to come in and meet with Sam Feist, who was then the DC bureau chief. “So I immediately forwarded it to my agents at UTA, and I was like, ‘this seems bad.’” Indeed it was. “I went into Sam's office and he was like, look, as you've probably figured out in the three hours since we sent the email, you're gonna be let go.” Cillizza still had over a year on his contract, which meant CNN would continue to pay out both his salary and benefits, but any day-to-day involvement with the company was over.

This firing was arguably his first major setback in a 20+ year career. “Aside from losing my father and my father-in-law, it was the most difficult thing I've ever gone through, certainly the most difficult thing professionally.” It didn’t help that the entire event occurred in public. “When you get laid off as a public figure and it's in Politico, well, everybody knows about it. So you can't pretend like, Hey, I've got this next great opportunity coming. It was like the lead item in Playbook.”

Cillizza tried to stay off Twitter in the days following the news — after all, it wasn’t hard to guess how people would react — but he couldn’t help himself. “It's not like I went there being like, ah, Twitter will affirm that I'm actually a good human. Like I knew that wasn't what it was going to be, but I still went back to it probably more times than I should have. So yeah, it sucked.”

Probably the worst part was having to tell his children so they could be prepared if someone brought up the news at school. His younger kid, who was then in fifth grade, asked why it had happened, and Cillizza told the cliche about how these things happen, and it’s not how many times you get knocked down but how many times you get back up. “Here’s the wonderful thing about kids, though,” he said. “The eighth grader was like, I'm sorry, I bet that made you sad. And then the next day he was like, when are you taking me to practice?”

A newsletter emerges from the ashes

Cillizza spent the next few weeks in a state of shock. “It's not exactly like losing a loved one, but it's a kind of death of a certain image of yourself,” he explained. “Up until that day I had been able to tell myself that I was on a ladder slowly and consistently moving upward, and then what I thought of as linear progression sort of ended.” 

I asked him if he had any inkling then of what he wanted to do next. “My initial thought was not just that I have to find another media job, but I need another job in mainstream media. I need to get another job like the job I just had. I've got to replace at least a chunk of the salary, the profile, the opportunity, the health care.” His agents at UTA sounded optimistic about finding him a new role, but not many media executives were taking meetings so close to the holidays.

But Cillizza’s agents suggested he talk to one person who actually was still taking meetings. On December 22nd, he got on the phone with Sophia Efthimiatou, the head of writer relations at Substack. While Substack operates as a platform that anyone can sign up for, Efthimiatou works on a team that offers a sort of white glove treatment to its high-profile creators. Many of the folks on the team have niche specialties like finance, politics, and fashion, but Efthimiatou often floats across all content categories.

Efthimiatou described Cillizza’s demeanor as “humbled.” “I think he was probably still processing what was happening,” she told me in an October interview. He showed lots of interest in Substack, but he was also skeptical that an audience would pay him directly for his work. “He was a natural fit for this, even though he probably did not think that initially,” she said. “He was so used to, I think, having a structure around him. Sometimes what I've seen is that people think that the structure brings so much to the table for them that they don't know who they are without a newsroom around them.” But Cillizza was boisterous and clearly had both a strong personality and point of view — traits that Efthimiatou considers perfect for running a successful paid newsletter.   

Cillizza left that phone call intrigued by the Substack opportunity but still doubtful. What ultimately led to him posting there wasn’t entrepreneurial ambition, but boredom. “Some people were telling me to enjoy it, like you've got more than a year on your contract, just enjoy some of this time with your family.” That worked for the duration of the holidays, but then came the day his kids went back to school. “It was like January 9th or something. I drop them off at the bus at like 7:45 and I come back to the house and it's like 7:50 or whatever, and I'm like, what to do, what to do? And I looked at my calendar and the next item on it was to pick the kids up from the bus at 3:45. I'm like, well, okay.”

That day he published a short post to serve as a landing page he could link to from Twitter, and then a few days later he published a sort of manifesto explaining his “new theory of news.” Whereas most of the media put much of its focus on reporting the “what” — essentially the news as it happened — he would put his efforts into explaining the greater context of that news, hence why he called the publication “So What?” It sounded grandiose, but he was really just describing a continuation of what he had already done at CNN and the Washington Post, and indeed over the next few weeks he posted on a wide spectrum of topics ranging from Trump’s “low-energy” campaign to how seriously everyone should take Nikki Haley (remember, back then we were in the lead-up to the Republican primaries). 

Efthimiatou watched from the sidelines and would regularly send Cillizza feedback on his strategy. What struck her was that his content was still too buttoned up, too professional. “I kept pushing him,” she said. “I told him that everyone is here for you, and you don't want to bullshit the people who are there for you.” She urged him to occasionally take a break from politics and write more about his personal life.  

Gradually, Cillizza did begin to open up. In March 2023, for instance, he posted about the devastation he’d felt after learning his father-in-law had suddenly passed away (“This was a man who lived to inspire others to their best, to make sure they knew they had someone on their side who was solely concerned with them succeeding in whatever way they sought to define that.”). Later that year, he published a piece about his struggles to maintain adult friendships (“I have started to think of friendship like a muscle. If you don’t lift the weights, it shrinks. If you ignore it for too long, it atrophies — never to recover.”). Earlier this year, he wrote about the “unexpected joy” of driving his son to faraway soccer practices (“I have also really come to take pleasure in the silence we sit in most of the time. Him working. Or staring out the window. Or, occasionally, making a joke about the Henry V podcast he is sort of half-listening to as his nerdy dad nods his head and says stuff out loud like ‘I did not know that!’”)

To his surprise, these types of posts not only resonated with his audience, but they also triggered much higher paid conversions. “People responded in an extremely positive way,” recalled Efthimiatou. “It was like a surprise for him, and he said, ‘Oh, I can do this here, and it's fine.’ And I was like, ‘Yeah, you should actually lean in more to that.’” It was at that point that she saw the lightbulb go off in his head and he realized Substack could serve as more than just a holding pattern as he waited for his next mainstream media gig. “That’s when he became a true evangelist, because I think Substack ended up having such a positive impact on his psychology exactly when he needed that.” 

In addition to launching his Substack account, Cillizza also dusted off a YouTube channel he’d created all the way back in 2008 and started uploading new videos. For the first year or so, he’d write a script, record several takes, and then send the file off to a guy who he paid $200 to edit and polish the video. “After a year of making two or three videos a week, I had 5,000 YouTube subscribers, and I was like, this is not working.” So he switched up his strategy: instead of writing a script, he’d just turn on the camera and start talking. And then instead of sending it off for editing and production, he’d just immediately upload it to YouTube.

That strategy proved much more effective. In the last year, the channel’s subscriber base has grown by a factor of 10, and videos posted just within the last month have racked up over 800,000 views. That’s nowhere near the viewership he needs if he wants to make a living off YouTube Adsense, but then again he’s come to accept that his future career will depend on multiple revenue streams — a mixture that includes YouTube ad money, Substack subscriptions, his contract with Monumental Sports, and even teaching a course on political journalism at Georgetown University, his alma mater.  

Which brings me back to the question I started this piece with: is it enough? If his agents suddenly came to him with a full-time role at a mainstream media organization, would he take it?

He didn’t have a satisfying answer for me. “I like working in a newsroom,” he admitted. “I will say that. I miss being around people like my friend Paul Kane or Mark Preston or Jake Tapper. I like just being around people who've been in this industry for a really long time, and I miss interacting with them.” But regardless of whether that opportunity arises, he thinks the thing he’s built — and continues to build — can be enough. “You do not need to pity or cry for me. I'm doing just fine … It's not as big as I want it to be, but it's definitely a thing. It spits out enough money that allows me to live my life and not make major adjustments. And that's kind of cool, because it's just me and the keyboard really, you know what I mean? It’s something that didn’t exist in December 2022, and now it does.”