That’s alt-weekly, folks

A decade at the storied ‘Chicago Reader’ mirrored the struggles and triumphs of media across the nation.

That’s alt-weekly, folks

A decade at the storied ‘Chicago Reader’ mirrored the struggles and triumphs of media across the nation.

A series reflecting on the 2010s as we head into the new decade.

Two weeks after I started working at the Chicago Reader in the fall of 2011, the alt-weekly celebrated its 40th anniversary. There was a boisterous party at a loft in the city’s Pilsen neighborhood, where contributors and employees from every era of the publication’s history slammed drinks while wearing yellow and black clothing, the same colors of the Reader’s ubiquitous newspaper boxes. The mood was boozy and optimistic; the Reader had weathered tough times but the future looked rosy.

From its ascendant years in the 1970s until the early 2000s, the Reader made its money on classifieds and local advertisements and earned its journalistic reputation by giving talented writers as much space as they wanted to tell stories how they needed to be told. The extent of that coverage was (and still is) broad: a decades-long series of articles on police torture; a 14,500-word feature about brick salvagers; a 100-word takedown of Alien. The emphasis in “alternative weekly” was on the “alternative”: You knew you would read the opposite of what you’d find in the more conventional Tribune or Sun-Times, the city’s two major dailies. And though the writers had unusual freedom, that latitude was grounded by rigorous editors, fact-checkers, and proofreaders, all of whom ensured high standards.

By 2007, Craigslist had devoured most of the revenue from classifieds and an internal lawsuit forced the paper’s cofounders to sell. Ben Eason, the CEO of southern alt-weekly chain Creative Loafing, persuaded the owners that he could solve the Reader’s financial troubles. After he bought the paper he presented his solution: He eliminated the entire production staff and slashed the editorial budget. Eason’s brash ineptitude extended to his business acumen — he could never pay off the loan he took out to purchase the Reader, so his creditor, a hedge fund called Atalaya Capital Management, took over the publication and every other title in the Creative Loafing chain (which at that time included five other properties).

Mara Shalhoup, a prominent investigative reporter and top editor at the flagship Creative Loafing in Atlanta, had been named editor in chief of the Reader in mid-2011, inheriting a staff and paper on the brink of collapse. Mara had exquisite taste and a contemporary vision that was easy to buy into. Immediately after she started, she rehired Mick Dumke — a prolific features writer with a focus on city politics, who’d left the previous year to join an ill-fated local news outlet called the Chicago News Cooperative. She also sped up a redesign of the print edition, most prominently by adding a glossy cover and sending the music section to the back of the book, where it was flipped upside-down and called the B Side.

I was hired six months later as the “Digital Content Editor,” a newly created title that emphasized the Reader had its sights trained on an online-first future. At the time, the paper was still making a good chunk of its revenue on classifieds, but that money dwindled annually, and we presumed that web display ads, and eventually mobile ads, would catch up to once-lucrative print rates.

We were ready to improve the website, which required filling it with actual writing. Unfortunately, most of the staff was already working overtime to put out a paper every week — nominal staff writers were either copy editing or top editing whole chunks of the Reader — and our freelance budget was so low we couldn’t hire many outside contributors. There were blog quotas and scheduled posts, most of which generated in-house. Signs of burnout were evident, but there was a collective understanding that all our efforts were being done in pursuit of a common goal: restoring the Reader’s past success.

Six months after my first day, we pulled off an improbable, full-scale overhaul of the website. The renovation was cosmetic. We were still saddled with a restrictive content management system, or CMS, that made it feel like we were running the publication on a TI-83 graphing calculator, a holdover from a more digitally illiterate era. But our mischievous and beloved art director, Paul Higgins, had navigated around the system’s limits, adding stylish fonts and icons that helped the Reader avoid resembling other alt-weekly websites, which seemed like they were stuck in the early 2000s. The redesign was well received, and the feeling was that we were on an upward trajectory.

The story of how alt-weeklies eroded over the past 15 years tends to spotlight the same bad actors — Craigslist, rapacious owners, Facebook — but the decline was also a failure of the surrounding community.

Two weeks later we were all called into a meeting, where we were given two options: Either people would be laid off — we were never told how many — or we could take a five percent pay cut across-the-board and knock some full-time staffers down to part-time. No one wanted to go through another brutal wave of firings, so the decision made itself. Shortly afterwards we got an explanation for the pay reduction: The Reader had been purchased by Wrapports, a new media company headed by Michael Ferro, a venture capitalist who made his fortune on business software and already owned the Chicago Sun-Times. The price was just shy of $3 million. The Reader had occupied a five-story building near Michigan Ave. since 1983, with an enormous painted logo on the east brick facade, but Wrapports decided it didn’t want to pay its rent. That summer, we squirmed into the Sun-Times’ office on the Chicago River, which boasted a game room, free candy, and primary-colored furniture that half-assedly mimicked Google.

Once the Reader moved over to the Sun-Times, digital strategy turned into a comically overblown affair. We’d bounce 40 e-mails back and forth debating web headlines and trick out features with unnecessary supplements like audio and video. We were cognizant of the ways in which other media outlets were cravenly trying to goose Facebook or tantalize readers with clickbait about celebs, so we thankfully avoided those easy targets. But the payoff for all our agonizing over how to appear more web-savvy was unclear, and there were no signs that all our efforts were actually making us money.

The gains were particularly difficult to identify during the making of our special issues like Best of Chicago, which were time-consuming projects in pursuit of momentary bursts of web traffic. Some of these packages were carryovers from the heyday of print media, and didn’t cleanly apply to the logic of online publishing. Fall arts previews, for instance, started because most cultural institutions make big promotional efforts to get people back indoors as the weather cools down, so newspapers and magazines responded by creating a feature that they could sell around this seasonal push. But the internet doesn’t operate under the strictures of print production schedules or with the objective of appeasing local advertisers; it’s an endless expanse where scale dictates success.

On the print side, it made less sense to create special issues for local advertisers when many of them had long ago stopped buying space in the paper. Back in the ’90s, virtually every retail shop, music venue, gallery, and theater advertised in the Reader. Why did they stop? When I asked my friends who work in advertising, they’d usually say that it was much cheaper to advertise on websites and social media, where there are more eyeballs anyway. Which, duh.

A less-discussed but equally obvious culprit in the Reader’s struggle is that the ebbing of local print advertising is a byproduct of corporate infringement on urban life. Independent businesses support each other, and many of the ones that advertised in the Reader struggled to maintain that support as rents went up due to escalating property taxes and then-mayor Rahm Emanuel’s push to make Chicago more of a “global city.” It’s depressing when a Lululemon moves into a flower shop or a Yeti supplants a music venue — not just because a lame and ubiquitous company overtakes a local one with character, but because the collapse mushrooms outwards and other local businesses get hit with the shrapnel. The story of how alt-weeklies eroded over the past 15 years tends to spotlight the same bad actors — Craigslist, rapacious owners, Facebook — but the decline was also a failure of the surrounding community.

Not to take away blame from the Reader’s owners — they deserved most of it. “I won’t touch you guys,” Ferro told me at a grandiose Christmas party at a bowling alley shortly after the sale. “I don’t want you guys to change anything.” When I relayed that to J.R. Jones, the film editor and my closest friend at the paper, he said if it was true then Ferro was the smartest owner we could have. But there were two ways of looking at that statement: Wrapports might not fuck with us, but it wouldn’t invest in us either.

Neglected ‘Chicago Reader’ boxes, circa 2016/2017.

Neglected ‘Chicago Reader’ boxes, circa 2016/2017.

Neglected ‘Chicago Reader’ boxes, circa 2016/2017.

Instead, Ferro and Wrapports sunk $12.5 million into the Sun-Times Network, a dystopian, lobotomized website of aggregated news that bled money and went nowhere. Had Wrapports invested even a fraction of that sum in the Reader, it’s possible that the paper would have been profitable and successful for years — and the staff would be able to earn a livable wage. But what ownership knew, and what all media owners know, is that ultimately it will always be able to leverage the scarcity of editorial positions and the emotional investment of the employees to get people to work harder for less money.

The salary freezes and long hours persisted. Eventually, enough people decided it wasn’t worth it any longer. In a downtown conference room the color of an airport security office, the Newspaper Guild made their case for why we should organize. We volleyed arguments for and against unionization until a longtime staff writer became vocally irate. Sure, the wages in the ’90s weren’t great — but under the paper’s original owners the employees were at least treated well. You got freelance rates on top of your salary, and there were bonuses at Christmas. It was obvious that Wrapports treated us badly; we were exhausted and had little to show for it financially. The vote to organize, which took place in January of 2015, was unanimous.

Mara didn’t really have to worry about the union — a month later, she headed west to take over LA Weekly, which would go on to experience its own catastrophic ownership problems. Managing editor Jake Malooley ascended to interim editor, which soon became permanent. Jake came from Time Out Chicago, where he wrote a popular and lively front-of-book column each week. He was a fan of the Reader and seemed to understand its purview — we often stayed late at the office discussing things we wanted to do in the paper, whether it was restoring comic strips or creating a quarterly book review.

But we quickly realized that would be impossible under Wrapports, which provided few opportunities for creative decision making — and beyond that, by this point I’d spent years fantasizing about all the things we might get to do, if given the time and resources that, in a steadily deteriorating media landscape, were unlikely to suddenly materialize.

After three years of ownership, Ferro decided he didn’t want to ignore us any longer. Clearly burned over our unionization, he gave Sun-Times executives more say over the Reader. While they stalled bargaining sessions they decapitated our business side, firing all of the salespeople when they failed to hit impossible quotas. Now, Sun-Times ad reps would sell for both the Sun-Times and the Reader — but only after they hit their Sun-Times sales figures. There was also the matter of people having trouble actually getting the paper. We heard of delivery drivers leaving stacks of newspapers in alleys, and boxes filled with trash or defaced so terribly that pedestrians couldn’t see the cover of the week’s issue.

In 2016, Ferro bought Tribune Media, which owned the Chicago Tribune, and turned it into a national punchline called tronc, a messy portmanteau meaning “Tribune online content,” and yes, it was not capitalized. We stayed in the Sun-Times’ office, but the game room disappeared, along with the free candy. The new head of Wrapports transparently feigned interest in the Reader, so on weekends we’d stand outside of Steppenwolf Theatre, where he was on the board, and hand out postcards explaining our union drive before performances. The experience was clarifying. Older passersby loved the Reader and pledged their support, but many twentysomethings didn’t even know what it was.

We started using Slack, the now ubiquitous workplace messaging system. Slack made it easier for employees to work from home, which people did as often as they could. We cut down on emails, but on some days the office became a ghost town; maybe four people would show up. The erosion was ongoing: Our page count diminished at an alarming rate, and when people jumped ship, their positions went unreplaced; the glossy cover went away, along with many of our longtime advertisers. Reports emerged that Ferro was trying to buy us back for some ominous, undisclosed purpose. Staff meetings became tense under the pressure of the foreseeable prospect of the end of the Reader.

There was no new sales staff; the glossy cover wasn’t coming back; the website was left to languish without repair.

Midway through the year, a former alderman and gubernatorial candidate named Edwin Eisendrath pulled together a consortium of investors including the Chicago Federation of Labor, an organization comprising local unions. They snatched the Sun-Times and Reader away from tronc’s maw with $11.2 million in escrow to cover projected losses. The staff was cautiously optimistic, particularly because our path to a union contract accelerated given the Federation’s involvement and because our new owner cut a chipper, supportive figure. “Call me Edwin,” Eisendrath told us. Edwin was going to relocate us to a new headquarters in the West Loop, Chicago’s hot new tech neighborhood. We were invited to go over there and tour it.

What we discovered was a painfully obvious metaphor. The Reader would be stuffed in the shabby, frigid corner of a windowless loft, where we were expected to line up monitor to monitor. It was a low-budget attempt to replicate the open-floor plans of a start-up media company, and we’d already endured the process of trying to approximate a digital news outlet (and weren’t eager to do it all over again). We sat in meetings in which Edwin asked us “Who reads the Reader?” and then proceeded to dismiss our responses outright. There was no new sales staff; the website was left to languish without repair.

When I told Jake I was leaving at the end of 2017, he was compassionate. “Anyone can look around here and see that there aren’t many other options,” he said. I went to Chicago magazine, which is owned by Tribune Media. At the time, Michael Ferro was in charge, and I was reluctant to work for him again. But I’d always wanted to know how a monthly print magazine operated, and after years of low pay, 70-hour workweeks, and discouragement I was ready for a change. By this point, John Oliver had devoted a whole segment of his show to lambasting Ferro, who would step down in March of 2018 amid the fallout of a humiliating sexual-misconduct scandal.

The turmoil continued. Two weeks after I left the Reader, Jake returned from his honeymoon to a phone call letting him know he was fired. His replacement, Mark Konkol, lasted only a week, canned instantly after he approved a racist illustration on the cover of Democratic gubernatorial candidate J.B. Pritzker sitting atop a black lawn jockey.

In the summer of 2018, Eisendrath unloaded the Reader to a different group of investors who propped it up until last month, when the paper announced a move that seems promising: It will become a nonprofit. It’s foolish to speculate on the inner workings of a place you no longer go into every day — I hated when it happened while I was at the Reader — so this particular story ends here.

Growing up, I’d always assumed if you loved what you did at your job, then happiness and professional satisfaction would ensue as a result. In journalism, at least, I now know that’s naive. But you invest emotionally in what you love, and when that investment is out of your control, and the forces in charge treat it wantonly, the pain is deep and permanent. My experience is just a variation on a theme, which played out all across the country. There is almost certainly a similar recounting from former staff of the LA Weekly, Village Voice, Boston Phoenix, Baltimore City Paper, and on and on and on; the only difference is that the Reader somehow survived the apathy and cruelty of its owners.

The Columbia Journalism Review recently published a story about how Chicago has become one of the most innovative news towns in the country. The situation is promising, with younger, scrappier, and in particular more diverse organizations that are thinking creatively about ways in which journalism can persevere and better serve the city, like City Bureau, South Side Weekly, and The Triibe (which frequently collaborates with the Reader) .

Ironically, while many people were trying to figure out how traditional media should adapt to the internet, DNAInfo quietly became the most successful and admired local news outfit of the past decade by sticking to the most traditional model, assigning reporters to specific neighborhoods. But DNAInfo’s founder, Joe Ricketts, preferred to shut it down in 2017 rather than accept the staff’s unionization effort. Former DNAInfo reporters started Block Club Chicago, which has picked up right where DNAInfo left off.

But the days of filing two reviews a month for an alt-weekly and getting paid enough to make your rent? Having a staff position at a publication and eventually buying an apartment or house of your own? That seems unlikely. When I entered the media industry nearly 15 years ago, it was possible a writer could make a living by pursuing their own idiosyncrasies with a like-minded group of people. Instead, we had to watch as the bosses resented such a possibility because it didn’t conform to their idea of “innovation” and destroyed it.

With each passing year, the least interesting people have more and more of the money. The day before Thanksgiving, I sat in Chicago’s hot new food hall, owned by Time Out, overhearing someone talking about buying a condo in Tribune Tower, the hallowed high-rise that for nearly a century was the headquarters of the Chicago Tribune. Why did the owners of these two media properties opt to go the routes of restaurants and real estate? Simple. Because they couldn’t see an alternative.

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Tal Rosenberg is a writer and editor in Chicago.