Honestly, if you’ve lived in Chicago or even just passed through O'Hare and grabbed a tabloid off the rack, you know the Sun-Times. It’s the gritty, blue-collar younger brother to the Tribune. But the corporate entity behind it—Sun-Times Media Group—has a history so chaotic it makes a soap opera look like a documentary.
For years, people have been waiting for the other shoe to drop. We’ve seen bankruptcies, owners who ended up in federal prison, and a carousel of "saviors" who realized too late that the newspaper business is basically a burning money pit. But here we are in 2026, and the brand is still kicking. It's just... different.
What Actually Happened to Sun-Times Media Group?
The name "Sun-Times Media Group" used to represent a massive portfolio. Back in the day—we're talking the Conrad Black era of the 1990s and early 2000s—the company was known as Hollinger International. It didn't just own the Chicago paper; it had the Jerusalem Post, the Daily Telegraph in London, and a swarm of suburban weeklies.
Then things got messy.
Conrad Black was ousted and eventually went to prison for fraud. The company rebranded to Sun-Times Media Group in 2006 to try and distance itself from the scandal, but the timing was terrible. The 2008 financial crisis hit, advertising revenue cratered, and by 2009, the group filed for Chapter 11.
Most people thought that was the end. Instead, it was the start of a decade-long game of hot potato.
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- The Tyree Era (2009-2011): Local businessman Jim Tyree led a group that bought the company for a measly $5 million. He was a hero to the newsroom, but he died suddenly in 2011.
- The Wrapports Phase: A tech-investor group took over. They tried weird things, like firing the entire photography staff (yes, everyone) in 2013, thinking reporters could just take "good enough" photos with iPhones. It was a PR disaster.
- The Public Media Pivot: By 2022, the "group" structure basically dissolved when Chicago Public Media (WBEZ) acquired the Sun-Times. This turned it into a non-profit.
The Non-Profit Gamble: Is it Working?
You've probably noticed that the Sun-Times website doesn't have a hard paywall anymore. That’s the big experiment. When Chicago Public Media took over, they ditched the old model of "pay to read" and switched to "please donate if you like us."
It sounds risky because it is.
The merger was backed by a $61 million "dowry" from big-name foundations like MacArthur and Pritzker. That money was meant to be a runway to get them to 2026. Well, guess what? It’s 2026. That initial cushion is starting to look a lot thinner.
We’ve seen some growing pains. In early 2025, the organization had to offer voluntary buyouts to staff to keep the budget in check. Big names left. Rick Telander, the legendary sports columnist, and film critic Richard Roeper were among those who took the exit. It hurt the brand's "voice," but the leadership—currently led by CEO Melissa Bell and Editor-in-Chief Kimbriell Kelly—insists it's about long-term survival.
Realities Most People Get Wrong
People often think the Sun-Times is just a smaller Tribune. It's not. Historically, the Sun-Times Media Group thrived on being the "watchdog for the little guy."
Remember the Mirage Tavern? In the late 70s, the paper literally bought a bar to catch city inspectors taking bribes. That’s the DNA. Even through the corporate reshuffling, that investigative spirit is why people still care about the brand. If they lose that, they’re just another website.
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Another misconception: that the "Media Group" still exists as a corporate shark. It really doesn't. The "group" has been stripped down to its core Chicago assets. The suburban papers were mostly sold off to the Tribune years ago, and the international titles are long gone. It’s a lean, local operation now.
The "Fiscal Cliff" of 2026
We have to talk about the money. The non-profit model is a beautiful idea, but the "fiscal cliff" is a real thing.
The $61 million in grant money was never meant to last forever. The goal was to build a "membership" base—regular people paying $5 or $10 a month—to replace the lost ad revenue.
The stats are mixed. Digital audience is up—some reports say pageviews grew 55% after the paywall came down. But getting people to pay for something they can get for free is the hardest sell in business. The Sun-Times Guild (the union) has been vocal about this, pushing management to secure more revenue so they don't have to keep cutting reporters.
What This Means for You (The Reader)
If you're a Chicagoan, the survival of the Sun-Times matters because competition keeps the Tribune honest. If you're a media nerd, this is the "Chicago Model." If it fails here, the non-profit future for daily newspapers looks a lot bleaker.
Kimbriell Kelly, the first Black editor-in-chief in the paper's history, has been focusing on "reaching the whole city," not just the wealthy suburbs. That’s a noble goal, but it requires a lot of boots on the ground.
Actionable Steps for the "New" Sun-Times Era:
- Check the membership stats: If you’re tracking the health of the company, look at their annual impact reports. They have to be transparent now because of the non-profit status.
- Follow the Guild: The Chicago News Guild is very active. If you want the "real" story of what's happening inside the building, their Twitter/X feed usually has the tea on budget cuts or management shifts.
- Newsletter strategy: The Sun-Times has shifted heavily into newsletters. It's their primary way of "owning" the audience without relying on Google or Facebook's algorithm. If you want to support them without a huge bill, signing up for the "Morning Edition" is the easiest entry point.
The Sun-Times Media Group of the past is dead. The version that exists today is a non-profit hybrid trying to prove that local news doesn't have to die just because hedge funds stopped caring about it. It's a bumpy ride, but it's the only game in town.
Monitor the upcoming 2026 financial filings from Chicago Public Media to see if the "membership model" actually covered the gap left by the expiring foundation grants. That will be the ultimate tell for whether this experiment has legs.