Launched in 2002, this award has gone through some changes (hence the occasional notes in italics).
2002: Les Brownlee, John Callaway, Bernie Judge, Irv Kupcinet, Charles Nicodemus, Ed Rooney, Lois Wille
2003: Bob Crawford, Colleen Dishon, Georgie Ann Geyer, John White, John O’Brien
2004: Ray Coffey, Jerry Crimmins, John Drummond, Bruce Fine, Brenda Rotzoll, John Drury
2005: Bob Black, Richard Christiansen, William Mullen, Pam Zekman, Paul Zimbrakos
2006: Ron Kotulak, Carol Marin, Orion Samuelson, Jim Frost, Ed Baumann
2007: Laura Washington, Harlan Draeger, John Hultman, Joe Cappo, Mike Flannery, Phil Velasquez
2008: Andy Shaw and Fran Spielman. First time Lifetime Achievement Awards and Lisagors were presented at the same dinner.
2009: Phil Kadner and Mary Field
2010: Richard Longworth, Elizabeth Brackett, Roger Ebert
2011: Mary Ann Ahern and Mary Mitchell
2012: Clarence Page and John Cody
2013: Bill Kurtis, Tracy Baim, Karen Meyer
2014: Felicia Middlebrooks and Greg Hinz
2015: Linda Lenz, Harry Porterfield, Jon Hilkevich
2016: Robert H. Jordan Jr. and Mary Schmich
2017: three legendary Chicago reporters for their undercover work to break the famous Mirage Tavern investigative series in 1978.
Pam Zekman and Zay Smith, who were reporters for the Sun-Times, and Bill Recktenwald, who was chief investigator for the Better Government Association, worked together in this 25-part series where the Sun-Times bought a dive bar at 731 N. Wells St. in order to expose the misconduct of city inspectors on the take.
2018: Sheila Solomon and Nancy Stone
2019: Clarence Waldron and Jim DeRogatis
2020: Cheryl Corley and Greg Kot
2021: Bill Cameron and Dahleen Glanton.
The Headline Club changed its naming system for Lifetime Achievement awards in 2023. The club now names each class of honorees for the year they receive their awards, rather than the previous year. The 2023 change eliminated a “Class of 2022” but maintained the annual schedule with no break in awards.
2023: Dorothy Tucker, Rick Pearson, Phil Ponce and Chuck Neubauer.
2024: Craig Dellimore, Fred Mitchell, Tom Skilling and Roz Varon.
2025: Theresa Gutierrez, Chuck Goudie, Rummana Hussain, and Curtis Lawrence.