The 2000s
In 2000, the Sun-Times' new editors, Michael Cooke and John Cruickshank, tapped longtime staff reporter Mark Brown, who had considered himself an investigative reporter, to write a column that would anchor page two of the paper.
In 2000, longtime investigative reporter Charles Nicodemus retired from the paper at age 69. He died in 2008 at age 77.
In 2001, Sun-Times investigative reporter Chuck Neubauer quit the paper to join the Los Angeles Times' Washington bureau. Neubauer and Brown had initiated the investigation into U.S. Rep. Dan Rostenkowski that uncovered a variety of misdeeds that ultimately had led to Rostenkowski's indictment, conviction and imprisonment.
In April 2001, Sun-Times architecture critic Lee Bey quit to join the administration of then-Chicago Mayor Richard M. Daley as Daley's deputy mayoral chief of staff, responsible for downtown planning, rewriting the city's zoning code and affordable housing issues.
In April 2001, longtime Sun-Times horse-racing writer Dave Feldman died at age 85 while still on the Sun-Times' payroll.
In 2002, with Kuczmarski & Associates, the Chicago Sun-Times co-founded the Chicago Innovation Awards.
In May 2002, Sun-Times editors Joycelyn Winnecke and Bill Adee, who were at the time husband and wife, both quit on the same day to join the rival Chicago Tribune. Winnecke had been the Sun-Times' managing editor, and she left for a new post, associate managing editor for national news, while Adee, who had been the Sun-Times' sports editor for nine years, became the Tribune's sports editor/news.
In April 2003, the Sun-Times picked up the comic strip Beetle Bailey after the rival Chicago Tribune dropped it in June 2002 and gave up the rights to it in February 2003. The Sun-Times celebrated the arrival of Beetle Bailey with a page-one announcement.
In October 2003, famed Sun-Times gossip columnist Irv Kupcinet began including the name of his longtime assistant of nearly 34 years, Stella Foster, as the coauthor of his column. After Kupcinet died the following month at age 91, the Sun-Times kept Foster on and gave her the sole byline on the column, which now is known as "Stella's Column."
In 2004, the Sun-Times was censured by the Audit Bureau of Circulations for misrepresenting its circulation figures.
In February 2004, longtime Sun-Times political columnist Steve Neal died at his home in Hinsdale, Illinois, at age 54 of an apparent suicide.
In August 2004, longtime Chicago broadcast journalist Carol Marin began writing regular columns in the Sun-Times, mostly on political issues.
On September 28, 2005, Sun-Times columnist and editorial board member Neil Steinberg was arrested in his home in Northbrook, Illinois, and charged with domestic battery and with interfering with the reporting of domestic battery. With that, Steinberg, who had been at the Sun-Times since 1987, entered a treatment facility for alcohol abuse. On November 23, 2005, Cook County prosecutors dropped the charges against Steinberg after his wife said she no longer feared for her safety. On November 28, 2005, Steinberg returned to the Sun-Times' pages after going through a 28-day rehabilitation program at a nearby hospital, and he gave readers his version of the events that led to his arrest: "I got drunk and slapped my wife during an argument." Steinberg also reported that he and his wife were "on the mend," and that he was working toward sobriety.
In the spring of 2006, a variety of longtime Sun-Times writers and columnists took buyouts, including sports columnist Ron Rapoport, sports reporter Joe Goddard, society and gardening columnist Mary Cameron Frey, book editor Henry Kisor, page designer Roy Moody and photographer Bob Black. Classical music critic Wynne Delacoma also took a buyout, and left the paper later.
In August 2006, the Sun-Times fired longtime Chicago Cubs beat writer Mike Kiley. Then-Sun-Times sports editor Stu Courtney told the Tribune that the dismissal of Kiley, who had joined the Sun-Times from the Tribune in 1996, was a "personnel matter I can't comment on." The Tribune{{'s}] Teddy Greenstein called Kiley "a fierce competitor."
In September 2006, longtime Sun-Times environment reporter Gary Wisby retired as part of the same group of writers who were offered and accepted buyouts in the spring of 2006.
In February 2007, noted Sun-Times columnist Debra Pickett quit upon returning from maternity leave. The reasons for her departure were differences with her editors over where her column appeared and the sorts of assignments being handed to her.
On July 10, 2007, the paper announced: "We are returning to our liberal, working-class roots, a position that pits us squarely opposite the Chicago Tribune—that Republican, George Bush-touting paper over on moneyed Michigan Avenue."
In January 2008, the Sun-Times underwent two rounds of layoffs. In its first round, the Sun-Times fired editorial board members Michael Gillis, Michelle Stevens and Lloyd Sachs, along with Sunday editor Marcia Frellick and assistant managing editor Avis Weathersbee.
About two weeks later, the Sun-Times underwent more staff reductions, laying off columnist Esther Cepeda, religion reporter Susan Hogan/Albach, TV critic Doug Elfman and onetime editor Garry Steckles, while giving buyouts to assistant city editors Robert C. Herguth and Nancy Moffett, environmental reporter Jim Ritter, copy editors Chris Whitehead and Bob Mutter, editorial columnist Steve Huntley (who remains with the paper now as a free-lance columnist), and special Barack Obama correspondent Jennifer Hunter. Also taking a buyout was longtime health and technology reporter Howard Wolinsky. Two other staffers, business editor Dan Miller and deputy metro editor Phyllis Gilchrist, resigned. Reporter Kara Spak initially was reported to have been laid off, but she wound up staying with the paper.
In August 2008, high-profile sports columnist Jay Mariotti resigned from the Sun-Times after concluding that the future of sports journalism was online. Mariotti later joined ESPN.
In October 2008, the Sun-Times gave buyouts to noted TV/radio writer Robert Feder (now a blogger with Time Out Chicago) and longtime auto writer Dan Jedlicka. The paper also laid off two members of its editorial board: Teresa Puente and Deborah Douglas.
In November 2008, the Sun-Times dropped its "Quick Takes" column, which Sun-Times columnist Zay N. Smith had written since 1995. Smith wrote the column from home, and the Sun-Times discontinued the column and informed Smith that it needed him back in the newsroom as a general assignment reporter. The paper's union complained, noting that Smith had permanent physical disabilities that made it difficult for him to be mobile. Smith later left the paper.
In March 2009, sports columnist Greg Couch left the Sun-Times after 12 years to join AOL Sports.
On March 31, 2009, the newspaper filed for bankruptcy protection.
On October 9, 2009 the Sun Times unions agreed to concessions paving the way for Jim Tyree to buy the newspaper and its 50 suburban newspapers. Of the $25 million purchase price, $5 million was in cash, with the other $20 million to help pay off past debts.
In November 2009, Sun-Times sports editor Stu Courtney quit to join the rival Chicago Tribune's Chicago Breaking Sports website.
In December 2009, the Sun-Times hired sports columnist Rick Morrissey away from the rival Chicago Tribune.
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