Long before email blasts, social media posts, and livestreamed press conferences, there was shoe leather, conviction, and a relentless belief that the message mattered enough to fight for it.
I learned that lesson as a college student working with Jesse Jackson—a lesson delivered not in theory, but in fire. I remember. As I read today’s news stories on Jackson’s passing, I remember the early days of press coverage. Jesse’s press relationship was curious and dynamic. Today, as I read, he is more myth than real.
In those early days, communications for Operation Breadbasket were as grassroots as it gets. After Saturday meetings at the Parkway Ballroom, David Wallace—Jesse’s classmate from Chicago Theological Seminary and his first press secretary—and I would assemble press packets. Photographs by Jack Finley and John Tweedle. Photos were developed in a dark room. We had a tight operation. Typed releases. Carefully written captions. My first press job was to write captions that David carefully read over.
Then we would hit the streets. We would drive downtown and then head to the south and west sides.
Our first stops were the major dailies—Chicago Tribune and Chicago Sun-Times—followed by the Black press: The Chicago Defender, The Chicago Crusader, The Chicago Citizen, and The Independent Bulletin.
The difference in reception was immediate—and painful.
The downtown press ignored us.
The Black press saw us.
Week after week, for nearly a year, we knocked on doors that did not open. We delivered stories that were not told. We brought evidence of movement—thousands gathering, ideas forming, power organizing—and received silence in return.
I reached a breaking point.
At a staff meeting, I announced I was quitting. “This is a waste of time,” I said. “They are not paying attention to us.”
Jesse’s response was swift and sharp.
“Did you say quit?”
“Yes.”
“We don’t ever quit,” he said. “We continue the work—and figure it out.”
That was not just a reprimand. It was a philosophy.
And the very next week, everything began to change.
The Door That Opened…
Sometimes history shifts not with a grand strategy, but with a single open door.
At the Sun-Times building, I saw an open door—and walked in. Inside was Irv Kupcinet, the most influential columnist in Chicago, preparing his Sunday column and his television program, Kup’s Show.
I handed him our press package.
He was curious—engaged in a way others had not been. He asked questions: Who attends these meetings? How many people come? What’s happening there?
I told him that day, about 2,000 people had gathered. Our guests included rising stars like Bill Cosby and Robert Culp, who had just launched I Spy. They fly in from California.
I invited him to see it for himself.
He came.
And once he saw Jesse Jackson in action—commanding, rhythmic, organizing, inspiring—he wrote about it. Not everything. But enough. He didn’t write a story; he wrote items for his gossip column.
Enough to make others pay attention.
Strategy Meets Persistence…
While I was knocking on doors locally, David Wallace took a different route. He mailed our story to national outlets—The New York Times, The Washington Post, Los Angeles Times.
And they responded after a while.
They wanted to know: Who is this Jesse Jackson?
The validation came from outside Chicago before it came from within the city that works. That, too, is a lesson. I developed a quiet but powerful alliance with Stella Foster, Kupcinet’s secretary. She became one of my best friends and provided great advice on handling the press and on writing for attraction. Some Fridays, she would call: “What’s happening this week?”
And we made sure there was always something happening.
Guests like Aretha Franklin, Sammy Davis Jr., and Cannonball Adderley became part of the narrative. The meetings were not just gatherings—they were cultural and political intersections.
After a few mentions by Kup, the press could no longer ignore us.
The Complicated Courtship…
But attention did not guarantee accuracy.
Reporters miscounted crowds—writing “hundreds” when thousands filled the room. They simplified complex messages. They missed cultural nuance. They often misunderstood Jesse entirely.
I spent hours in newsrooms pushing back, arguing, correcting, and challenging.
So did Jesse.
He would call reporters directly—forcefully, but with charm—demanding clarity, insisting on context. He refused to be misrepresented quietly.
The relationship between Jesse Jackson and the press was never passive. It was a constant negotiation.
Daily news columnist Mike Royko coined nicknames like “Jesse Jetstream,” suggesting he moved too fast, inserted himself everywhere, and chased the spotlight.
Was it criticism? Yes.
Was it also recognition? Absolutely.
Royko and others acknowledged something undeniable: Jackson had energy, reach, and timing that the press struggled to keep up with and questioned whether they should cover. Too often, the press was racist; structural media racism exists.
Jesse was always moving—organizing nationally during the week, reporting back locally on Saturdays. He connected issues before others saw the connections. He spoke in a cadence that blended politics, culture, and moral urgency.
For some reporters, that was hard to translate.
Opening Doors That Had Been Closed…
Jesse’s influence on the press extended beyond his own coverage.
He pushed Black journalists to expand their reach—to move beyond “urban affairs” and into politics, policy, and opinion. He challenged editors, elevated voices, and demanded inclusion.
Journalists like the late Vernon Jarrett were not just observers—they were participants in a broader intellectual and political dialogue. Sunday morning conversations with Jesse, David, and Vernon were rigorous, unfiltered, and deeply consequential. Vernon played a key role in the election of Harold Washington by explaining the history and politics of the Black community to his audience.
Jesse didn’t just want coverage.
He wanted transformation.
Loved, Criticized—Never Ignored…
Over time, the press developed its own internal rules around Jesse Jackson: not too much coverage, limited front-page exposure, controlled access. The press suppressed Black leadership with strained and contained coverage.
And yet, they could never fully contain him.
Corporate Critic: Tribune writer John Kass often used the moniker “King of Beers” to refer to Jackson’s role in negotiating beer distributorships for his family, sometimes contrasting it with Jackson’s public persona as a champion of the poor.
Political “Shakedown” Critique: Kass frequently accused Jackson of using his clout to pressure corporations for personal or familial gain, in 2021 labeling him a “corporate shakedown artist“.
Political Interference: Kass often portrayed Jackson as a “high-profile black political leader” who inserted himself into local and national politics to gain power.
But across the spectrum—admiration or criticism—there was one constant:
Respect for his force and point of view.
When Jackson ran for President in 1984, the mainstream white press went crazy, asking, “What does Jesse really want?” It was a perfect question for him to answer, as he discussed equity, fairness, and justice. We welcomed the question if they would write our unedited answer.
Frank Watkins became Jesse’s press person. He took Jesse’s yellow legal pad notes and found the right rhythm with the press for activity, explanation, and messaging. Frank wrote position papers on issues. He was a keen strategist. I was often in the background, with a “what do you think?” question or a “guess what?” answer. It was a Watkins research paper that gave Jesse the grounds to run for President. He made the case on the southern Black population demographics. He made the case with others that if the established elite political top guys wouldn’t run, why not you? He outlined the case for a run that made history. He was a futurist. Jesse may not win, but he will change the game, ready or not.
The Lesson That Endures…
What I learned in those early days still applies today.
The press is not a passive vehicle. It must be engaged, challenged, cultivated, and sometimes outmaneuvered. That’s why a free press is important in a democracy. Racism is real in the media; it even lives with Black reporters sometimes, even today.
Access is not given. It is earned—and sometimes taken.
And most importantly: you don’t quit when the door is closed.
You knock again.
Or you find another door.
Or, if necessary, you build your own.
Jesse Jackson did all three.
And in doing so, he didn’t just get his message out—he reshaped how the message could be heard.
And in my very own way, as I think about it, I started N’DIGO, a newspaper with a new perspective for similar reasons. It was time for new news. And it’s time for us to look at Jesse in real time, not as a mythical man.
