Retired and revered Chicago political reporters talk about today's polarized and vitriolic country

CBS News

4 days ago

Mike Flannery, Derrick Blakley, and Craig Dellimore are three of Chicago's most respected journalists, all having covered politics until they each retired in recent years.
Recently, they sat down for a roundtable discussion to talk about their careers as witnesses to history, and the polarized, hate-filled, and even violent state of today's national politics.
Go back two decades, and you would find all of them — and Jim Williams, who joined them all for the roundtable discussion — working at the old CBS Chicago broadcast center at 630 N. McClurg Ct. Flannery, Blakley, and Williams all worked together at Channel 2 News, as we used to call CBS News Chicago, while Dellimore worked upstairs at WBBM Newsradio.
Flannery, Blakley, and Dellimore have all always shared a passion for and a fascination with politics and government, both national and local.
Flannery's journalistic career spans 50 years.
"I came to Chicago because Mike Royko's 'Boss' was assigned readings in two classes — his book, 'Boss.' I found it fascinating, and it was so entertaining — and I got a job at the Sun-Times right out of school. I'd been the editor of my college paper," said Flannery, "and I got here, and I just fell in love with the place."
Flannery started at the Sun-Times in 1973 after graduating from Georgetown University. He moved to CBS Chicago in 1980, where he spent 30 years — beginning when Jane Byrne was mayor of Chicago and Ronald Reagan was taking on Jimmy Carter for president, and continuing into the first term of President Barack Obama.
Flannery worked alongside many legends of the anchor desk at Channel 2 — Bill Kurtis, Walter Jacobson, Don Craig, Harry Porterfield, Lester Holt, Linda MacLennan, Carol Marin, Antonio Mora, and Rob Johnson, to name a few. In 2010, Flannery moved to Fox 32, where he served as political editor under three more presidential administrations and covered three more mayors before retiring in 2023.
Blakley's journalistic career spans 47 years. A graduate of Northwestern University's Medill School of Journalism for undergrad and the University of Illinois Urbana-Champaign for his master's, the Chicago native started out at the Chicago Tribune in 1976. He moved to television with CBS affiliate WBNS-TV in Columbus, Ohio, and then worked for CBS News on the network level — based in Chicago; London; and Bonn, West Germany.
Traveling throughout Europe and the Middle East as a network news correspondent, Blakley impressed viewers with his eloquence and sophistication.
Blakley then became a reporter and anchor at Chicago's NBC 5, where he worked for 16 years before joining Channel 2 in 2003. At CBS Chicago, Blakley anchored the 4 p.m. news with Mary Ann Childers, and then moved primarily to reporting on all different topics — eventually becoming the station's political reporter before retiring in 2019.
"One of the unique things about Chicago compared to other big metropolitan areas is that everybody was interested in Chicago politics," Blakley said. "It was bloodsport. It was combat in a different realm — whether in Chicago, you were talking about the machine, and it was the machine and those who were against the machine."
Dellimore, a graduate of Columbia University in New York, said counting his time as a copy boy at the New York Times in his college days — which we do — his journalistic career spans 52 years. He joined WBBM Newsradio in 1983, and became political editor for the station in 2001 — succeeding the legendary Bob Crawford, who had held the post since the station went all-news in 1968.
As political editor, Dellimore covered numerous campaigns, controversies, and national political conventions, and hosted the "At Issue" public affairs show. He retired in June of this year.
"What I found fascinating was that you could see the politics of the city because it was so public, and so active. You could see it evolve," Dellimore said, "and my time in Chicago started in 1983, when Harold Washington was being taken seriously as a mayoral candidate."
In their recent roundtable discussion with Williams at the longtime Chicago journalists' haven the Billy Goat Tavern on Lower Michigan Avenue, the veteran political journalists talked about their careers and covering Mayor Washington, the Council Wars, and other historic and often tense political moments.
But more so, they talked about the state of today's politically polarized country — with Americans whipped up by social media and partisan news outlets, reporters being insulted, and politicians increasingly having become targets of violence.
"There has been a lot of political rhetoric that demonizes opponents, and can lead to the creation of hatred," Blakley said. "There has to be less vilification of an opponent."
As to navigating that polarization and breaking through people's echo chambers and silos, Dellimore said such a task is far easier said than done.
"I'm not sure we can entirely break through all of that, because let's face it, if people don't like the way we are reporting, they go to people who are reporting the way they like. People believe what they already believe," Dellimore said. "But what we can do — what we have to do — is to keep telling the truth."
An extended version of the roundtable discussion: