During the 2008 election cycle, he has published several pieces detailing the relationships between Barack Obama and various Chicago church leaders such as Jeremiah Wright as well as former member of the radical Weather Underground Organization William Ayers.
In August 2008 Kurtz attempted to obtain the University of Illinois at Chicago's Annenberg records detailing the professional relationship between Obama and Ayers. Kurtz's efforts to explore the association between the two men has been controversial.
In September 2008 Kurtz published his initial findings from his study of the Chicago Annenberg Challenge records, writing, "As [Chicago Annenberg Challenge] chairman, Mr. Obama was lending moral and financial support to Mr. Ayers and his radical circle." Kurtz also wrote, "The CAC's agenda flowed from Mr. Ayers's educational philosophy, which called for infusing students and their parents with a radical political commitment, and which downplayed achievement tests in favor of activism." According to Kurtz, the educational program on which Obama and Ayers collaborated was ultimately unsuccessful: "CAC's in-house evaluators comprehensively studied the effects of its grants on the test scores of Chicago public-school students. They found no evidence of educational improvement.
Stanley Kurtz's reporting became the subject of an "Obama Action Wire" issued by the Obama campaign. This release, issued in advance of Kurtz's August 28, 2008 appearance on the popular Chicago radio show, "Extension 720 with Milt Rosenberg," requested Obama supporters to call WGN radio prior to his appearance and ask them not to allow Kurtz to on the air, and to call into the show "Us[ing] the talking points above" and "report back on your call". Zack Christenson, executive producer of "Extension 720 with Milt Rosenburg," told the Chicago Tribune that the Obama campaign was asked to have someone appear on the show, and declined the request. Christenson further said that this was the largest response from a campaign that Extension 720 has ever received, stating "This is really unprecedented with the show, the way that people are flooding the calls and our email boxes." A followup Chicago Tribune story, "Obama campaign flubs a defense", said that "The grass-roots response was weak," but also editorialized that "Kurtz really had nothing new to add" to the Obama–Ayers controversy.