Chicago, IL – The Chicago Headline Club is proud to announce the recipients of the 2026 Lifetime Achievement Award: Cheryl Raye-Stout, Jim Williams and Lynn Sweet. The award recognizes their exceptional contributions to journalism and tireless efforts to give readers, listeners and viewers the truth they needed to know about Chicago.
All three will be celebrated Friday, May 8, at the Peter Lisagor Award ceremony at the Union League Club. The award recognizes the best of Chicago journalism and is named for Peter Lisagor, the Chicago Daily News’ Washington bureau chief from 1959 to 1976.
The Lifetime Achievement Award committee found that each of these tremendous journalists has delivered important and meaningful stories over their many years in their fields of expertise. The citizens of Chicago and Illinois have benefited greatly from their work.
Cheryl Raye-Stout, WBEZ
Cheryl Raye-Stout has worked in the Chicago radio market for more than forty years and is one of the first women to cover sports here. One of the barriers she broke was being the first female reporter to enter locker rooms for Chicago major sports teams. Since 2001, she has served as the sports contributor for WBEZ-FM. Previously; Cheryl has contributed to WMAQ-AM and WMVP-AM as a producer, talk show host, and as a lead sports reporter. She won Peter Lisagor awards, UPI, and AP awards, for her work on the Bulls Championship Rallies and the Chicago Marathon. She announced a White Sox game with Don Drysdale, and broke key stories of Michael Jordan’s decision to play baseball and his return to the NBA. Cheryl has covered both Bears’ Super Bowl appearances, all six Bulls Championships, all three Blackhawks Championships, White Sox and Cubs playoffs, including the 2005 and 2016 World Series and the 2021 Chicago Sky WNBA Championship.
A graduate of Columbia College in Chicago, she taught in the radio department as an adjunct teacher for 20 years. Cheryl grew up in the Austin area of Chicago and played sports when girls were not allowed to participate in organized sports. Title IX came one year too late.
She lives in the Northwest suburbs with her husband, Dr. Glenn Stout and has one son, Jaxon.
Jim Williams, CBS News Chicago
Jim Williams is a CBS News Chicago contributor and former co-anchor of the 11 a.m. and 4 p.m. newscasts.
Williams began his broadcast journalism career in 1977 at WGN-TV, where he was a newswriter, producer and reporter. He also wrote newscasts for WGN Radio.
From 1992-1997, Williams was Chicago Mayor Richard M. Daley’s press secretary. He supervised media relations throughout city government.
For four years, he was a correspondent for ABC News, reporting across the country for “World News Tonight with Peter Jennings” and “Good Morning America.” For “Nightline,” Williams covered China’s crackdown on the spiritual group Falun Gong.
He joined CBS Chicago as a general assignment reporter in December 2002.
Williams has won several journalism awards, including two Emmys and a Peter Lisagor Award. In May of 2018, he was inducted into the National Television Academy of Arts & Sciences’ Silver Circle for his lifetime of work in Chicago television.
Williams was born and raised on Chicago’s South Side. He is a graduate of Kenwood High School and Columbia College.
Williams and his wife, Joyce, have four adult children.
Lynn Sweet, Chicago Public Media
Lynn Sweet is a special correspondent for Chicago Public Media and previously was the Washington Bureau Chief and a columnist for the Chicago Sun-Times. She has appeared frequently on CNN and other national outlets as an analyst.
Sweet transferred to Washington in September 1993 after serving as the Sun-Times chief political writer. Other assignments in her 50-year career include covering Cook County government and civil courts, the state legislature in Springfield and a short stint as part of a gossip columnist team.
Sweet was among the first reporters in the nation to evaluate political ads for accuracy and part of the early wave of political journalists who embraced blogging.
She has covered 17 national political conventions. Her reporting has taken her through city wards, across the nation and to Kenya, South Africa, Israel, Canada, Europe and Mexico.
Sweet has a master’s degree from Northwestern University’s Medill School of Journalism and an undergraduate degree from the University of California at Berkeley. She also attended the University of Illinois at Urbana-Champaign. Sweet is a former fellow at Harvard University’s Institute of Politics and the University of Chicago’s Institute of Politics. She was inducted into Northwestern University’s Medill Hall of Achievement in 2006 and was named by Washingtonian Magazine as one of the capital’s “50 Top Journalists” in 2009.