Remembering Reverend Jesse Jackson: A Personal Reflection
Both tears and sweat are salty, but they render a different result.
Tears will get you sympathy; sweat will get you change. — Rev. Jesse Jackson
Sympathy costs nothing. Change costs everything — time, persistence, and the willingness to step in when others step back.
On February 17, 2026, Chicago lowered its flags as the nation marked the passing of Reverend Jesse Jackson Sr. at 84. Tributes described him as a servant leader, coalition builder, and voice for the marginalized.
All true. But Jackson measured himself not by sympathy earned, but by change delivered — especially when institutions fell short.
I saw that lesson play out long before I fully understood its reach.
Applying the Model Early: Hyde Park and the Walgreens Project
I first put those lessons into practice in 2007, while teaching carpentry and construction at Hyde Park Career Academy, when Walgreens began building a new store at 67th and Stony Island. It was a major investment in a majority-Black neighborhood, and to me the question was simple: who was going to benefit?
So I reached out to the local alderman’s office and pushed a straightforward idea:
My students will help build the store. They will give them jobs.
We secured about five union construction positions.
For high school students earning around $20 an hour, it wasn’t symbolic — it was life-changing.
My students literally helped build that Walgreens.
But the job site also exposed them to the realities of the trades at the time:
racist graffiti,
KKK symbols in the porta potty and unfinished brick walls on the construction site,
contractors who treated the place like their own territory.
We documented everything and made it clear the students weren’t going anywhere.I told the company plainly:
If you don’t want my students working, they’ll sit in the office on your dime. But you’re not pushing them off this job.
Years later, some of those students came back and told me:
Kugler, you were right. I made a lot of money. Thank you.
That experience reinforced the lesson I would later deepen through Operation PUSH: leverage opens doors, but persistence keeps them open.
Then Came the Displaced Teachers
Beginning in late 2009, I became part of a grassroots effort working out of Operation PUSH on Chicago’s South Side. This wasn’t a job or an official role — it was a collective of educators and community members responding to the layoffs and reclassification of Black teachers.
Working alongside organizers like Rosita Chatonda and Antoinette “Toni” Barnes, I watched how Reverend Jackson and his network turned frustration into strategy and strategy into pressure.
That work came into sharp focus in late June 2010, when more than 100 displaced tenured teachers gathered at PUSH headquarters after facing layoffs under CPS leadership. Many were literacy coaches and support staff, disproportionately African American women who suddenly found their roles reclassified and stripped of union protections.
At the time, institutional support was thin. The Chicago Teachers Union, navigating a leadership transition, told many of the affected educators they would largely have to fend for themselves.
So the organizing happened anyway.
- We grouped teachers by classification.
- We collected intake forms.
I drafted a group grievance that 78 educators signed and filed on June 30, 2010. The demands were clear: halt the terminations, restore positions, enforce due process. Jonathan Jackson spoke about repairing a broken system through community empowerment rather than corporate priorities.
Jackson’s Network and the Power of Leverage
Jackson’s network expanded the fight.
At that PUSH meeting: NAACP attorneys Rose Joshua and George Eddings addressed the group,
- They offered partnership,
- And they pointed to successful litigation strategies used in other cities.
Mr. Eddings specifically referenced a successful lawsuit filed by the New York teachers union that stopped 19 school closings, showing the group that strategic litigation could work when combined with community pressure.Their presence showed what leverage looks like — when community organizing connects to serious legal expertise.
Years later, many of those educators saw tangible results through arbitration wins, contract enforcement, and sustained advocacy. But the fight didn’t end there.
A Decade-Long Battle Over Who Counts as “Union”
Most of the educators — many of them instructional coaches — hadn’t simply lost jobs. Their positions had been removed from the bargaining unit and reclassified. What followed was a decade of organizing, documentation, and legal battles.
Working as a field representative with these individuals, I pushed to have them recognized again, often clashing with union leadership, which at the time viewed many of the roles as management positions that should remain outside the unit. I disagreed, and the pressure continued.Nearly ten years later, that sustained effort paid off. The positions were restored to union coverage and incorporated into the 2019 contract.
Today, many of those former instructional coaches are classified as Instructional Support Leaders (ISLs) — a title that reflects the long fight to bring those roles back under union protection.That’s not a press release. That’s a material change in people’s lives.
The Strategy Behind the Man
Jackson wasn’t only a civil rights icon — he was a strategist. He understood a hard truth about racism in America: you may not change every mind, but you can change who gets hired, who gets paid, and who gets a chance.
His approach was pragmatic. When companies came to Chicago, he demanded outcomes. Opportunity coming into a community had to include the community.
Not symbolic gestures — paychecks.
That strategy diversified workforces, opened boardrooms, and created pathways that rhetoric alone never could. Protest was the opening move; negotiation produced results.
The Measure of a Legacy
Today the language of change often sounds different — equity frameworks, investment initiatives, reform plans. But for many neighborhoods, the reality still comes down to the same fundamentals Jackson fought for:
- steady work,
- fair pay,
- and a path forward.
His legacy isn’t just the speeches or the marches. It’s the blueprint: organize, document, build alliances, and demand tangible outcomes.
Progress isn’t measured by promises — it’s measured by who gets hired, who gets paid, who moves forward.
Reverend Jackson taught generations that dignity comes from economic participation and collective power.
The tools he left behind — persistence, strategy, and leverage — remain as relevant as ever.Tears may bring sympathy.
Sweat brings change.
Rest in Power, Reverend Jesse Jackson. The work continues.
Caption: More than 100 teachers, most of them to be terminated on July 1 on orders of Chicago Public Schools Chief Executive Officer Ron Huberman, were at the June 29 meeting at Operation PUSH on Chicago’s South Side. Above, Rosita Chatonda (right side, back) speaks to the group about how grievances and possible litigation could be organized. Substance photo
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