After 50 years, dean of Chicago television’s political reporters calling it a career

He arrived in Chicago as part of an idealistic, new breed of college-educated reporters only to find a City Hall press room still characterized by Chicago-style graft and ethnic and racial slurs that would be unimaginable today.

He leaves 50 years later, at a time when the business he loves has been so “hollowed out,” its very future is uncertain.

Mike Flannery, political editor of Fox-32 Chicago and host of his weekly interview program, “Flannery Fired Up” is finally calling it a career. His last day on the job will be June 30.

Now 72, Flannery simply says it’s time to slow down and smell the roses. His immediate plan is to travel with his wife — to Ireland and other places they both haven’t seen — and visit grandchildren who live more than 1,000 miles away.

After that, he’ll go through the offers he’s already received to serve on the boards of Chicago nonprofits, and decide which to accept, if any.

“I’m not gonna just sit around and read and twiddle my thumbs. I’m gonna do something,” said Flannery, who jumped from newspapers to television in 1980, lured by a 50% pay hike that, at the time, raised his annual salary to $38,000.

“In some ways, I hate leaving. But I’m really excited. … It’s been 50 years. Ten mayors. Eight governors. Half a century is long enough. … This seems like a good time.”

Fox 32 News Political Editor Mike Flannery, (second from left) leading a roundtable discussion in March during the Chicago mayoral campaign with candidates Brandon Johnson (left) and Paul Vallas (right). Also participating are Flannery’s Fox 32 colleagues Anita Blanton (center) and Scott Schneider.

In a wide-ranging interview, Flannery reflected on his long, distinguished career that began on June 18, 1973, when he started at the Sun-Times after graduating from Georgetown University.

Flannery is the son of a World War II veteran. His dad spent two years in a V.A. hospital recovering from internal injuries he suffered while serving in Guam, and died while Flannery was still in high school.

His father’s early death created “financial hardships,” but scholarships made it possible for Flannery to attend Catholic high school and pricey Georgetown University in his hometown of Washington D.C.

At Georgetown, two professors assigned “Boss,” the 1971 book by Mike Royko, longtime columnist for the Chicago Daily News, Sun-Times and Tribune. It told the story about the era of the all-powerful Chicago Mayor Richard J. Daley.

“I was hooked. I said, ‘Wow. I want to go to Chicago,” Flannery recalled.

It wasn’t long before the wide-eyed, well-educated kid from D.C. whose Catholic pride had swelled during the presidential election of John F. Kennedy was disabused of his idealism. He arrived at a time when “racial epithets were part of the daily conversation” in press rooms at City Hall as well as at the old police headquarters at 11th and State streets.

Mike Flannery (rear) behind Chicago Mayor Richard J. Daley. Richard Stone, City Hall reporter for WIND-AM (560), is at left.

Mike Flannery (rear) behind Chicago Mayor Richard J. Daley. Richard Stone, City Hall reporter for WIND-AM (560), is at left.

“There were these sort of casual ethnic references to Italians and Polish people. There were also some terms for Irish people and Jewish people, Black people and Hispanics. That was just sort of in the air. Things are very different today,” Flannery said.

As intolerable as those ethnic and racial slurs were, Flannery said he was equally “stunned” by what he called the “ugly under-belly” of the City Hall press room at that time. Gifts — including cash and cases of liquor — would be offered to beat reporters and accepted by some, most notably during the Christmas holidays.

This was in 1974, when Flannery was the understudy to Harry Golden Jr., who covered City Hall for the Sun-Times.

“Harry drew the line at all that stuff. Harry was disdainful of our colleagues who did take those cash offerings. I admired Harry for that,” Flannery recalled.

“Harry once told me a story that one of the other reporters came up to him. … They were covering a Zoning Committee meeting. And that reporter came up to him and said, ‘Harry, how much would it be worth if you were to agree not to report on one of the items that’s on this agenda today?’ And Harry said, ‘No can do. Let’s end this conversation right now. I’m gonna cover this meeting.’”

Refusing to name names, Flannery said there was a Sun-Times reporter back in those days who “routinely fixed parking and traffic tickets.” He or she would call then-Chief Traffic Court Judge Richard LeFevour, who subsequently went to prison during the infamous judicial corruption investigation known as “Operation Greylord.”

“Maybe there’s an accounting to be had for how the media participated in some of these things that later ended up becoming exposed to the public and being so ugly,” Flannery said.

Mike Flannery in the WBBM (Channel 2) newsroom.

Mike Flannery in the WBBM (Channel 2) newsroom — more than a few years ago.

“I remember going out one night to dinner with one of my colleagues who had been drinking too much. He was driving. … Our wives were in the car. He gets pulled over on the Drive. And the officer comes up and this reporter says, ‘Officer, is there any way that I can pay the fine now?’”

The ever-present topic of political corruption came up again when Flannery started reminiscing about the 22-year-long tenure of Chicago’s longest-serving mayor, Richard M. Daley. For all Daley did and the legacy that he left behind, there was the dark cloud of political corruption and contract cronyism that permeated the Daley administration culminating in the Hired Truck, city hiring and minority contracting scandals.

“I think it was the environment that he grew up in. That sort of thing was in the air and in the water,” Flannery said of Daley, whose son got a city sewers contract while his patronage chief and streets and sanitation commissioner were ultimately convicted for rigging city hiring to benefit pro-Daley armies of political workers.

Flannery called it Daley’s “blind spot.”

Most of the Chicago mayors he has covered — particularly the “one-termers”— had their own blind spots.

Former Mayor Michael Bilandic’s was on display during the 1979 blizzard. As the storm continued, the CTA was ground to a halt, infuriated voters were told to park in school lots still buried in snow and their mayor was in denial.

“My most enduring memory is Bilandic telling colleagues, telling friends — as he was clearly in political trouble — ‘Hey, when I go out and meet people, they say nice things to me,’” Flannery recalled.

“He didn’t see it coming, the Jane Byrne upset. … And Byrne didn’t see what was coming from Harold Washington.”

Byrne’s downfall was her husband, Jay McMullen, a former Chicago Daily News and Sun-Times reporter. She allowed McMullen to “talk her into making a deal with the guys she had run against.” That is, City Council members Fred Roti, Edward Vrdolyak and the recently retired and indicted Edward Burke.

Washington, Flannery said, once told him “I wouldn’t be in the mayor’s office” if not for those deals Byrne made.

Mike Flannery with Cuban dictator Fidel Castro in 1999, during Illinois Gov. George Ryan’s trip to Cuba.

Mike Flannery with Cuban dictator Fidel Castro in 1999, during Illinois Gov. George Ryan’s trip to Cuba.

Chicago’s next one-term mayor was Lori Lightfoot. Her blind spot, according to Flannery, was having the hubris to misinterpret her landslide victory over Cook County Board President Toni Preckwinkle in April 2019.

“She didn’t recognize how wounded Toni Preckwinkle had been by the Ed Burke scandal. It was ludicrous,” Flannery said.

“A friend of mine happened to be present for an event that Lightfoot held out in California, a fundraiser, and just recounted to me the almost hilarious version that Lightfoot presented of her first-term victory. She misread that electorate and what that vote was about. And I think it crippled her.”

Former Mayor Rahm Emanuel’s weakness, Flannery said, was his inability to empathize with the people of Chicago. If he had that ability, he would have known that video of the police shooting of Laquan McDonald needed to be released no matter what the city’s policy was.

That’s even if you believe — and many people don’t — that Emanuel did not deliberately keep the tape under wraps until he was safely reelected.

Flannery had nothing but praise for Emanuel, who used his enormous political capital to tackle some of Chicago’s most intransigent problems during his two terms as mayor.

“I’ll tell you this: The business community misses him. I do think Brandon Johnson could benefit from talking to him. I hope they have talked — particularly with this new committee Mayor Johnson has created to try to find $800 million in taxes that the business community would go along with,” Flannery said.

“Rahm understood that cities are on the brink. It’s not just Chicago. It’s across the country … and in some other parts of the world as well. We have to grow. The economy has to grow. That’s what creates tax revenue. Rahm just understood that in his bones and he was brilliant at it.”

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