Chicago Sun-Times

• 1. A City Paper's Long Life

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  The Chicago Sun-Times landed on doorsteps for the first time on the 4th of December 1941, the day Marshall Field III's Chicago Sun published its debut issue. Three days later, the Japanese attack on Pearl Harbor upended the country. That timing planted the paper's roots in a moment of national rupture, and for the decades that followed, the Sun-Times would find itself entangled in some of the most dramatic chapters of Chicago and American life. How does a tabloid born in wartime become the city's second-largest paper, win eight Pulitzer Prizes, and then survive bankruptcy, multiple ownership changes, and the collapse of print advertising? The answers stretch across eight decades of corruption stings, star columnists, corporate betrayals, and one very famous film critic.

• 2. Origins and Early Voices

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  Jacob Burck arrived at the Chicago Times in 1938 as a cartoonist and went on to draw nearly 10,000 cartoons over a 44-year career, winning a Pulitzer Prize in 1941. He was one of the first distinctive voices at the paper that would eventually become the Sun-Times. The modern paper formed in 1948 when two predecessors merged: the Chicago Sun, founded by Marshall Field III, and the Chicago Daily Times, a tabloid that had been publishing since 1929.

  The advice column Ask Ann Landers debuted in 1943, written under a pseudonym by staff writer Ruth Crowley. Crowley answered readers' letters until 1955, when Eppie Lederer, the sister of Dear Abby's Abigail van Buren, took over the role. That same year the column launched, Irv Kupcinet's "Kup's Column" also made its first appearance, beginning a run that would continue until Kupcinet's death in 2003.

  Famed cartoonist Bill Mauldin, a two-time Pulitzer Prize winner known for his World War II illustrations, made the Sun-Times his home in 1962. The following year, he drew one of his most celebrated works: a mourning statue of Abraham Lincoln, rendered in response to the November 1963 assassination of John F. Kennedy. Roger Ebert joined the paper as a staff writer in 1966 at just two years out of college, and was named film critic a year later.

• 3. The Mirage and the Prizes

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  Eight Pulitzer Prizes mark the Sun-Times' record of ambitious journalism. The winners span Tom Fitzpatrick in General Reporting in 1970, Jack Dykinga in Feature Photography in 1971, and Roger Ebert in Criticism in 1975, making Ebert the first film critic ever to receive the prize. Art Petacque and Hugh Hough won in General Reporting in 1974, followed by John H. White in Feature Photography in 1982, Jack Higgins in Editorial Cartooning in 1989, and Frank Main, Mark Konkol, and John J. Kim in Local Reporting in 2011.

  Among the paper's most audacious journalism was the 1977 Mirage Tavern investigation. Sun-Times reporters bought and operated a saloon on Wells Street, using it to expose a pattern of civic corruption and bribery. City officials were investigated and photographed without their knowledge across a 25-part series. The articles drew considerable public attention, but a Pulitzer nomination stalled because some judges felt the undercover operation constituted entrapment.

  In January 2004, a six-month investigation by Tim Novak and Steve Warmbir broke the story of the Hired Truck Program scandal. The paper had a long history of holding Chicago's institutions accountable, rooted in a period under Field Enterprises when it was described as populist and progressive, independent of the city's Democratic establishment while leaning Democratic.

• 4. Murdoch and the Rupture

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  In 1984, Field Enterprises co-owners Marshall Field V and Ted Field sold the paper to Rupert Murdoch's News Corporation. Roger Ebert later described the first day of Murdoch's ownership in his blog: "He walked into the newsroom and we all gathered around and he recited the usual blather and rolled up his shirtsleeves and started to lay out a new front page." Ebert wrote that Murdoch ordered large, garish headlines and led the paper with a story about a North Shore rabbi accused of holding a sex slave. The story turned out to be seriously flawed. Ebert noted, "Well, actually, it didn't sell papers. There were hundreds of cancellations."

  The political stance of the paper shifted markedly rightward, while the front pages tilted toward the sensational. Ebert observed that the Sun-Times, which had been placing above the Chicago Tribune on lists of the ten best newspapers in the United States, never took the step forward it had been positioned for. Mike Royko, the Pulitzer Prize-winning columnist who had come to the Sun-Times from the Chicago Daily News in 1978, defected to the rival Tribune.

  Murdoch sold the paper in 1986 for $145 million in cash in a leveraged buyout, acquiring the television station WFLD to help launch the Fox network. The buyer was an investor group led by the paper's publisher, Robert E. Page, and the New York investment firm Adler & Shaykin. Just months later, the Sun-Times hired gossip columnist Michael Sneed away from the Tribune, and in February 1987 the popular Ask Ann Landers column left the paper after 31 years for the rival Tribune. The resulting search for a replacement drew more than 12,000 responses from people aged 4 to 85.

• 5. Ownership Carousel

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  Adler & Shaykin sold the Sun-Times to Hollinger Inc. for about $180 million in February 1994. Hollinger was controlled by Canadian-born businessman Conrad Black. After Black and his associate David Radler were indicted for skimming money from Hollinger International through retained noncompete payments from newspaper sales, both were removed from the board and Hollinger International was renamed the Sun-Times Media Group.

  By July 2011, the paper announced it would close its printing plant on Ashland Avenue in Chicago, eliminating 400 printing jobs and outsourcing printing to the Chicago Tribune. The move was estimated to save $10 million a year. The Sun-Times had already been distributed by the Tribune since 2007.

  The paper filed for bankruptcy protection on the 31st of March 2009. On the 9th of October 2009, Sun-Times unions agreed to concessions allowing Jim Tyree to buy the newspaper and its 50 suburban papers. Of the $25 million purchase price, $5 million was in cash and $20 million went toward paying off past debts. Tyree died in March 2011 under sudden circumstances. In July 2017, a consortium including private investors and the Chicago Federation of Labor, led by Edwin Eisendrath, acquired the paper from then-owner Wrapports. In March 2019, a new group backed by Michael Sacks and Rocky Wirtz took control.

• 6. Going Nonprofit

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  On the 30th of January 2022, the Sun-Times formally merged into Chicago Public Media, the nonprofit organization that owns WBEZ, Chicago's National Public Radio affiliate. A nonbinding agreement for the deal had been announced in September 2021. The final arrangement was backed with $61 million from several philanthropic organizations, and the paper transitioned to a nonprofit model.

  In October 2022, the Sun-Times dropped its digital paywall and subscription model, shifting instead to a voluntary membership-based approach that encourages donations from readers and sponsors. The paper's headquarters, which had been on Wabash Avenue before 2004 and then at 350 North Orleans from 2004 to 2017, moved to Navy Pier after the merger. WBEZ leases 45,000 square feet at that location for both radio and newspaper functions.

  In March 2025-35 employees, including 23 journalists at the Sun-Times and five business employees at WBEZ, took voluntary buyouts. That represented a loss of 20 percent of total staff at Chicago Public Media. The same month, the paper announced it would no longer publish editorials, ending a tradition that had stretched back to the paper's origins in the 1940s.

• 7. Stars, Scandals, and Stumbles

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  Roger Ebert remains the Sun-Times' most recognized writer. He worked at the paper from 1967 until his death in April 2013, making him both the paper's longest-serving film critic and the first film critic to win a Pulitzer Prize. Irv Kupcinet's daily column ran from 1943 until his death in 2003 at age 91; his longtime assistant of nearly 34 years, Stella Foster, took over the byline and remained until 2012.

  Pete Souza left the Sun-Times in 1983 to become the official White House photographer for President Ronald Reagan, serving through the end of Reagan's second term in 1989. He later returned to the same role for President Barack Obama. Lisa Myers served as the paper's Washington correspondent from 1977 to 1979 before becoming Senior Investigative Correspondent for NBC News.

  The Sunday edition of the 18th of May 2025 drew nationwide attention for a "Summer Reading list for 2025" that included AI-generated content featuring nonexistent books and fabricated quotes. The list appeared in a 64-page promotional insert written by Marco Buscaglia, who admitted to using AI and not fact-checking the material. The insert had been licensed from King Media, a subsidiary of Hearst, and also appeared in the Philadelphia Inquirer. That episode added a new chapter to a paper with a long record of both celebrated investigative work and public stumbles.