The Enterprise AI Failure Casebook

A newspaper printed an AI-made summer reading list of books that do not exist

The Chicago Sun-Times inserted a licensed special section that no one in its newsroom had reviewed, and 10 of the 15 books on its reading list were invented.

Chicago Sun-Times (Chicago Public Media) · May 20, 2025 · Updated October 31, 2026

On Sunday, May 18, 2025, the print and e-paper editions of the Chicago Sun-Times carried a special section titled "Heat Index: Your Guide to the Best of Summer." It held hammock instructions, summer recipes, smartphone advice and a list of 15 books to read that summer. Of the 15, 10 titles and descriptions were false.

The paper's circulation department had licensed the section from King Features, a unit of Hearst. Members of that department worked with King Features to select and insert it. They did not send the pages to anyone on the editorial team. The section ran under a Sun-Times banner, with no note that a third party had produced it.

The Sun-Times sold premium editions for an extra $3 each, bundled with the Sunday paper. Producing one took the newsroom weeks or months, so it had scaled back to fewer each year. The circulation department wanted to keep hitting revenue goals and found a supplier in King Features. The first King Features edition ran in May 2024. Melissa Bell, who became chief executive of Chicago Public Media, the paper's parent, in September 2024, was asked whether to continue. She later wrote that she did not deeply investigate the editions and approved them, so as not to lose the revenue. A second edition followed that November, then the Heat Index.

On Tuesday, May 20, at 6:04 a.m., a photo of the reading list was posted to Bluesky. At 8:44 a.m., Chicago Public Media's chief operating officer emailed Bell that some of the purchased content was "potentially made up." Later that morning, a reporter at 404 Media published an interview in which the King Features freelancer admitted using an AI agent. That day the Sun-Times said the list "was created through the use of an AI tool and recommended books that do not exist," and that the section "was inserted into our paper without review from our editorial team."

King Features said in a statement, quoted by the Sun-Times, that it has a strict policy against the use of AI to create content. It said the freelancer used AI without disclosing it, and that it was ending its relationship with the freelancer.

On May 29, Bell published a note listing five human mistakes, the fifth her own approval. The paper had removed the section from its e-paper and told subscribers they would not be charged for that edition. It changed its editorial policy: any third-party licensed content must say where it comes from, must not be presented as the newsroom's own, and must be reviewed by a new Standards team with editors from the newsroom. It said it did not plan to use other editorial sections from King Features, and would keep its comics and puzzles from the company. Bell wrote that the content would have broken the paper's draft AI policy had it been made in-house without review, and that an AI Oversight Committee drawn from the newsroom, product, legal, insights, sponsorships and enterprise systems would vet that policy.

What failed

The Sun-Times had a draft AI policy that required fact-checking and editorial review of AI-generated work, but it applied to what the newsroom made. Content the circulation department bought from a supplier reached readers through a different door, with no editorial review and no label. The circulation department trusted the supplier's editorial standards, and the supplier's own ban on AI was broken by a freelancer who did not disclose it. The chief executive approved the arrangement as a revenue line, without looking closely at the editions. The paper's own fix was to have a new Standards team of newsroom editors review licensed content and to label where it came from.

Sources

1. Chicago Sun-Times, Melissa Bell, Chicago Sun-Times response to May 18 special section, May 20, 2025, Paragraphs 2 and 3 (the section, King Features, the AI-made list); paragraph 5 (freelancer, no editorial review, no acknowledgment); paragraph 6 (King Features statement); "What we are doing" list (no charge to subscribers, e-paper removal)
2. Chicago Sun-Times, Melissa Bell, Lessons (and an apology) from the Sun-Times CEO on that AI-generated book list, May 29, 2025, Opening paragraphs (contents, 10 of 15 false); "Human mistake No. 4" and No. 5 paragraphs (circulation department, $3 editions, approval in September 2024); the Tuesday timeline (6:04 a.m., 8:44 a.m., 10:46 a.m.); the closing paragraphs on the AI policy, the AI Oversight Committee, the Standards team, the e-paper removal, no charge to subscribers, and King Features