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ST. LOUIS — In October, Chris Keating gathered the staff of the Riverfront Times at the El Milagro Azteca restaurant near the newspaper’s office and shared plans for the future.

Keating had recently taken sole ownership of the RFT and three other weekly newspapers after splitting from his partners in Euclid Media Group.

A new reporter would be added to the RFT, already his largest newspaper. His new company, Big Lou Holdings, was in “acquisition mode.â€� He had just agreed to buy City Pulse, a weekly in Lansing, Michigan. He teased another purchase, which would turn out to be Sauce, the ºüÀêÊÓƵ food magazine.

“It sounded like things were good,� Daniel Hill, RFT’s former editor-at-large, said of the staff meeting.

Just seven months later, Keating sold the RFT, erasing the alternative weekly’s foothold in the city’s cultural landscape after almost five decades. His other publications remain in operation.

Keating at first remained quiet about the sale. RFT employees, many of whom lost their jobs, and readers were left wondering how the situation unraveled so quickly. Free weekly newspapers have struggled for years, though several former employees say Keating made matters worse with brash business decisions.

Keating also faced personal financial issues — ones that would have made the already difficult job of keeping a free weekly newspaper financially viable even more daunting.

Since 2013, the Internal Revenue Service has filed six federal tax liens against Keating for unpaid personal income taxes. The missed payments date back to 2006. The most recent IRS lien was filed this past December for unpaid 2021 taxes of $20,000. The IRS has released the oldest of those liens. But five IRS liens against Keating, covering most tax years since 2012, remain in place and list unpaid taxes totaling nearly $200,000.

The unpaid balance may never have reached that sum; Keating could have entered repayment plans with the government. But the IRS only releases liens when they are paid in full.

Mark Milton, an attorney who helps clients with federal tax liens, said the IRS tends to get more aggressive as liens age, and it can levy money from personal bank accounts to collect past-due taxes if a payment plan isn’t worked out. IRS liens can make it next to impossible to borrow money.

“In a business like (the RFT), they’re going to want a personal guarantee,� Milton said.

In an interview this week with the Post-Dispatch, Keating insisted the sale of the RFT was not related to his tax debts. He sold the publication because revenue was worse than anticipated at the beginning of the year, Keating said, and he was stretched thin managing his other publications.

Keating also said his tax debt is now paid off and that the IRS should be filing the lien releases soon. The money to pay back the government did not come from the RFT sale, he added.

“You’re not getting rich off of this business in any way shape or form,� Keating said. “So the RFT sale, no, had nothing to do with it.�

IRS liens also make a mortgage difficult, if not impossible, to obtain. Keating does not own any property under his name in ºüÀêÊÓƵ or ºüÀêÊÓƵ County, according to property records. He rents a 5,800 square-foot, four-bedroom, six-bathroom house in a private Richmond Heights subdivision, records show. The home is appraised at $1.35 million.

A few years ago, in 2018, the IRS liens listed his address as a $1.4-million home on a private lane adjacent to Bellerive Country Club in Town and Country. He didn’t own that property, either.

According to his former executive assistant, Keating also rented apartments in Detroit and Louisville, where Big Lou Holdings owns the Detroit Metro Times and the Louisville Eccentric Observer. Mackenzie Dean, who was Keating’s assistant from May to December 2022, said he claimed he needed the apartments because he frequently traveled to oversee the papers, then owned by Euclid Media.

Keating said he no longer rents an apartment in Detroit, though he still has the one in Louisville. With the amount he travels, he said, the apartments are cheaper than hotel stays.

Regardless, it would be “a stretch� to suggest his lifestyle hurt the bottom line of the RFT, he said.

“Since day one of owning Riverfront Times or forming Big Lou, I’ve never taken a paycheck out of the business in any way shape or form,� Keating said. “Every bit of money, whatever, that possibly could has gone in to support Big Lou, Riverfront Times all the other papers. Any other suggestion would definitely be ludicrous.�

The fate of the RFT, meanwhile, remains unclear. Other than confirming the new owners were not from ºüÀêÊÓƵ, Keating declined to reveal whom he sold the publication to, saying he is bound by a non-disclosure agreement.

Weekly newspapers with storied histories in larger markets, such as New York’s Village Voice and LA Weekly in Los Angeles, have become “ghost newspapers,� mostly republishing old stories from their archives and sister publications while earning ad revenue from the online traffic, with little overhead.

After remaining static for weeks, the RFT’s website posted two new articles last week. Artificial intelligence detectors suggest the stories may have been written by chatbots. The posts were removed by the weekend.

Keating said he had nothing to do with the stories and is unaware of the new owners’ plans.

He stood by the sale of the RFT as a good business decision, though he lamented the layoffs that ensued.

“I invested very heavily, wanted to make RFT a flagship in the alt weekly industry,� he said. “I believe we did on the journalism side. I stand by that. But again, just because you’re producing great journalism does not always equate to great revenue.�

Some of Keating’s former employees agree he was dedicated to local journalism.

Ben Westhoff, who served a three-month stint as RFT executive editor in 2022, said Keating approved the hire of five editorial staffers in that time.

“It was as big an alt weekly staff as you would have found in the whole country,� Westhoff said. “There was genuine optimism, and it was a very solid newsroom. I give Chris credit for having a vision and trying to invest in the journalistic product.�

Career in alt weeklies

Keating has spent nearly his entire career in the alternative weekly publishing world, rising through the ranks of New Times Media, the publisher of the Phoenix New Times that grew to dominate the publication niche through acquisitions, including its purchase of the Riverfront Times from founder Ray Hartmann in 1998.

In 1996, Keating began working for the Miami New Times as an accountant. Three years later, he was promoted to headquarters in Phoenix to become corporate financial operations manager, according to the Association of Alternative Newsmedia. He was named vice president of financial operations at New Times in 2001.

In 2008, he moved to a different media group, Times-Shamrock Communications, and became publisher of the San Antonio Current. In 2010, he became publisher at another Times-Shamrock publication, the Cleveland Scene, according to the AAN.

Then, in 2013, he and Michael Wagner, along with Andrew Zelman and Dan Zelman of Cleveland, formed Euclid Media Group. They bought the Times-Shamrock’s alt weeklies in Detroit, San Antonio, Cleveland and Orlando. Wagner, also a New Times veteran, had been the RFT’s publisher from 2002 to 2007, and he later worked at Times-Shamrock as publisher of the San Antonio Current.

In 2015, their group purchased the RFT, adding it to a portfolio that would grow to eight weeklies. By the next year, Keating moved to ºüÀêÊÓƵ from Cleveland to become the RFT’s publisher.

When the pandemic hit, alt weeklies nearly went under as the venues and restaurants they relied on for advertising shut their doors. The RFT almost ceased print operations and much of its staff was laid off.

As the coronavirus receded, the RFT began rebuilding, gradually hiring back staffers. The publication in 2021 also moved from Downtown West into new offices on Shaw Avenue in the Hill neighborhood. Former employees say they remember when everyone got new desks and office furniture around early 2022.

But there were still serious issues with the business model.

Alternative weeklies rose to prominence decades ago with music and bar coverage alongside muckraking journalism, relying heavily on classified ads in print. The loss of print advertising and the shift to subscription-based business models left alt weeklies particularly strained. Many tried to fill the gap with events and a push to boost web traffic.

“The classified ad market died more than a decade ago, and since these things were largely free, that left them only with the river of nickels that comes with digital publishing, which is not enough to keep the lights on,� said Gabriel Kahn, a professor at the University of Southern California’s Annenberg School of Communication and Journalism. “The casualty list grows every day.�

By August 2023, Euclid Media split into two. Keating said he and Wagner always wanted to own their own publications and had a mutual parting of the ways.

Big Lou Holdings took over the RFT, along with weeklies in Detroit, Louisville and Cincinnati. Wagner took the papers in San Antonio, Orlando, Tampa Bay and Cleveland under his new company, Chava Communications. Chava later sold the Cleveland Scene to a publisher in that city.

“Whether it’s great restaurant criticism or a deeply reported story that explains the most important issues facing our communities, people rely on these publications,� Keating said in a news release at the time. “I intend to make sure they not only survive but thrive in this new era.�

Two months later, Keating bought Sauce magazine. The purchase of the Lansing, Michigan paper, which he had mentioned at the October staff meeting, never closed.

The RFT had been profitable in recent years, including 2023, according to Keating. But he conceded that maybe he hired too many people after the pandemic. And the loss of some large advertisers this year was a sign of how “things can change on a dime� in the industry, he said.

The RFT had the largest online traffic among Keating’s publications, making it more attractive to a buyer. Costs were also higher, “two to three times� above his other publications, he said.

He didn’t realize the buyer would let the entire staff of 11 go, and he “scrambled� to find jobs for six of the employees elsewhere in Big Lou, Keating said.

“I think it was the right business decision,� he said. “But in my heart, 100% it’s been absolutely brutal to part ways with it.�

‘A trigger finger’

The financial challenges facing the RFT came with an often rash management style by Keating, several former employees said in interviews.

While the news staff was mostly stable, the environment for marketing and advertising staffs could be “a little more volatile,� said Doyle Murphy, the RFT’s editor in chief from 2019 to early 2022.

Keating seemed “quick with his decisions sometimes,� Murphy said.

“There might be a whole bunch of people who’ve been hired, and then a few months later, a couple of them were still there,� Murphy said.

Jamila Jackson, a former social media coordinator, put it more bluntly.

“Chris has a trigger finger,� she said.

Jackson said her first boss, the marketing director, was fired around Christmas 2021, after Jackson had worked at the RFT just a couple of months. The next seven months were a whirlwind. She worked “every day, all day from sunup to sundown,� Jackson said, posting to social media and planning events and promotions across the four markets where Keating oversaw Euclid publications.

“It got to the point where every five minutes I’m checking my phone, afraid he’s going to text me asking why didn’t I post,� Jackson said.

Before the RFT’s United We Brunch event in February 2022, the venue said it could no longer provide bottomless drinks. Keating “lost his mind� with the marketing staff, Jackson said, and “started cussing out everybody in the room, which is not uncommon.�

Jackson was fired in July 2022 for what she said was a typo in an online event flyer.

In February 2024, Keating hired Laura Bassett, a former Jezebel Magazine editor and Huffington Post reporter, to oversee Big Lou’s publications.

“Twenty days into the job, I woke up to an email from Keating threatening to fire me if I was uncomfortable ‘making staffing changes,’ aka firing the entire staff of a beloved local newspaper,� Bassett wrote in a post on Substack.

She wrote that she talked Keating “off the ledge.� But she didn’t last long in the job. Bassett was laid off a few weeks after starting and told it was because of “severe budget woes.�

Keating “said he’d hoped to see a bigger jump in (digital) traffic across his portfolio sooner, that 90 days just wasn’t fast enough,� she wrote.

When reached by the Post-Dispatch, Bassett declined to comment but said the newspaper where Keating wanted layoffs was not the RFT.

Keating said he never fired anybody “on a whim.�

“If I fired anybody, it was absolutely for cause,� he said. “And I take those decisions seriously.�

The most recent RFT executive editor, Sarah Fenske, said on a ºüÀêÊÓƵ Public Radio program that Keating tried hard to save the publication, or at least find a local buyer.

“I have a lot of respect for Chris,â€� Fenske said on “ºüÀêÊÓƵ on The Airâ€� shortly after she and other staffers were laid off. “I know that he meant right by this publication. I don’t think that this is the solution that he wanted.â€�

‘It’s truly odd’

After weeks lying dormant, the RFT’s website started to show signs of life on June 13.

A short post about Gov. Mike Parson denying clemency to a man on death row published that night. The article said the inmate’s “execution date is approaching,� but neglected to mention the man, David Hosier, was executed two days prior. The next day, a post about a Nashville police officer accused of appearing in a porn site video was published on the RFT’s “arts and culture� section.

The stories were credited to Ryan Smith, whose website describes him as a percussionist and educator in Austin, Texas. He freelanced and taught in the Kansas City area after attending the University of Missouri-Kansas City conservatory, according to the site.

Smith did not respond to messages from the Post-Dispatch. His social media accounts went private shortly after. An email listed for Smith on the RFT website is not in service.

Adding to the intrigue: AI detection tools found a high use of artificial intelligence in Smith’s articles.

AI in journalism — or websites trying to pass off AI content as original journalism — is becoming increasingly common, even “inevitable,� said Peter Adams, senior vice president of research and design for News Literacy Project.

But the RFT website doesn’t show the tell-tale signs of an owner seeking to profit off AI-generated content, Adams said. He’s never seen a content farm created from the carcass of an established publication. And the RFT site only posted two articles, which wouldn’t serve the “click-bait� model, Adams said.

“One of the big threats posed by generative AI is the ability to just crank out endless stories and effortlessly populate a site, or a collection of sites, without paying anyone to write passable content,� Adams said. “That doesn’t seem to be the case here.�

Meanwhile, the RFT’s new owner and their plans for the website remain a mystery.

“If the former owner had any interest in journalistic ethics and was at all a responsible owner in the previous incarnation, they should be clear about who controls RFT now,� Adams said. “It’s truly odd that they’re not being transparent about that.�

Post-Dispatch reporter Monica Obradovic is a former employee of the Riverfront Times.