In 1983, something historic happened when Congressman Harold Washington ran for mayor of Chicago. It was more than a political campaign. People were galvanized. It challenged the city’s power structure, awakened the Black community, and changed Chicago politics forever.
The late Bill Berry, then head of the Chicago Urban League, went to corporate White Chicago, Chicago United, the organization formed after the King riots, to raise money for Harold Washington’s campaign. He discovered a painful reality: the corporate establishment was not prepared to finance the election of Chicago’s first Black mayor.
Berry understood the message. If Black Chicago wanted political power, Black Chicago would have to organize, mobilize, and finance it.
He called a meeting at Operation PUSH with Rev. Jesse Jackson. Around the table were Chicago’s most prominent Black businessmen, including John H. Johnson, George Johnson, Al Johnson, Cyrilo McSween, Ed Gardner, Al Boute, Jacoby Dickens, and Darryl Grisham. They are all deceased.
The message was simple and powerful.
“We can win this race. Harold can be mayor. We can win. But we have to come together. We simply don’t have White support.”
It was a defining moment. Mr. Barry cried. He said, “I thought they were our friends.” Jesse asked, “Why did you think that?”
Congressman Harold Washington, a political mastermind, knew winning would take more than speeches, promises, and political endorsements. He set four conditions for his candidacy: register 50,000 new voters, raise $250,000, run as the only Black candidate, and build a coalition.
Black Chicago went to work with a mission.
The clergy organized. Teachers organized. Students organized. Black businesses organized. Black media told the story when the mainstream press dismissed Washington’s candidacy as a political fantasy. Harold’s message reached Black listeners on the radio. Registration was ongoing and massive, resulting in over 150,000 new voters. The late Conrad Worrill and Dr. Bob Starks headed the voter registration drive. The Seaway National Bank President, Jacoby Dickens, took on fundraising.
People passed the bucket in churches. People sold blue campaign buttons on the street. Small house parties were held. Small checks were written. People gave what they could, because they understood something larger than the election itself. Change was in the air. Saturday mornings at PUSH became a place to gather and talk about the new politics in the air. Rev. Jackson was on point with fiery speeches. The political play was being called.
It became one of Chicago’s most remarkable grassroots political movements.
The rest, as they say, is history.
And now, more than four decades later, Chicago stands at another historic political crossroads.
This time, the issue is public education. We can make history by electing a Black man to the presidency of the School Board.
This time, the prize is leadership of Chicago Public Schools. The race is about capitalism and unions, or, if you prefer, unions vs. capitalism. The unions have taken a front-row seat in Chicago politics as they back candidates. Capitalists finance candidates so they can run massive TV commercials, both positive and negative.
This time, the question is whether Chicago’s newly elected school board will serve children and parents—or simply become another political playground for unions, wealthy donors, and politicians protecting their own interests. Even the alderman who chairs the Education Committee sits the race out, watching the wind blow instead of claiming real leadership.
A New Election. An Old Political Game.
For generations, the mayor appointed Chicago’s school board. The transition to an elected board was supposed to change that arrangement. It was supposed to give parents, taxpayers, and communities a greater voice in their children’s education.
But has the political structure really changed?
Or have we simply exchanged mayoral control for union control, billionaire influence, and political patronage?
Consider the candidates for school board president. The Chicago Teachers Union supports candidate Hilario Dominguez, SEIU supports Jessica Biggs, and Victor Henderson, an attorney and former CPA, is independent. He cannot raise money from White capitalists. The flimsy excuses for not funding him were that he didn’t have enough commercials or social media. But the real reason is that he is a Black, well-bred, educated man. This race echoes Harold. The November 3 election will select Chicago’s first directly elected school board president.
Victor Henderson brings the professional background of a trial lawyer and certified public accountant. His candidacy raises an important question about financial stewardship, independence, and how to govern a multibillion-dollar public school system.
His opponents, Hilario Dominguez and Jessica Biggs, bring different experiences and political relationships to the race. They bring the classroom and the union to the table. Can they handle the budget and governance of one of America’s largest school systems? Can they negotiate with Springfield politicians? The answer is probably no, but both are destined to become puppets of the billionaire and/or the union.
Those differences deserve public examination.
Who finances these campaigns? What do their endorsements mean? What obligations, if any, will candidates feel toward the organizations supporting them?
The Chicago Teachers Union and other labor and political organizations have a legitimate right to participate in elections. But the voters have an equally legitimate right to ask whether the next board president will answer to those organizations or to the public.
A school board president must be accountable to Chicago’s children, not merely to the political machinery that helped secure the office.
The Politics of Our Children…
One candidate has advanced ideas about expanding schools into community centers that provide additional services, including access to groceries and health care. A socialist approach.
Such proposals may sound compassionate. Some Chicago neighborhoods face genuine shortages of essential services. Can you imagine Jewel-Osco and Humana in the Schools? Compassion is not a budget.
Who pays for these services? Who operates them? What happens to the central mission of teaching children to read, write, think critically, and compete in a changing world?
As CPS faces serious financial pressures, every ambitious proposal must include a realistic financial plan. Schools cannot solve every social problem while struggling to fulfill their primary educational responsibility.
Then there is Jessica Biggs.
Public questions about her leadership at Burke Elementary School deserve serious scrutiny. Allegations involving attendance records, administrative practices, and student treatment must be evaluated against documented findings, with a fair opportunity to respond.
The issue is especially sensitive when the children affected are Black. Did she advance Black students, or did she suppress and ignore them? Her position with Urban Prep students suggests ignoring well-to-do students, who just happened to be Black males.
Would a predominantly White school on Chicago’s North Side have tolerated the same conduct? Would the response have been different? Would the political support have been the same?
These are questions worth asking, not conclusions to be assumed.
Children on the South Side deserve the same protection, educational excellence, and administrative accountability as children anywhere else in Chicago. Zip codes should not matter. Alderman should not matter.
Black children must never become political bargaining chips.
Black elected officials who endorse candidates should explain their decisions publicly. What qualifications, policies, and records persuaded them? What do they expect their endorsed candidates to accomplish?
An endorsement should be a statement of principle, not merely a political transaction.
Who Pays for Political Power?
Perhaps the most troubling question is what happens after the election.
The school board presidency is an unpaid position with enormous responsibility, a massive budget, and a substantial time commitment. In practice, the job takes about 60 hours a week.
How can someone devote the necessary hours to managing a major public school system without compensation? Hilario and Biggs ask, “Have you ever handled a budget?”
What employment arrangements will make that possible?
Will outside organizations create consulting contracts? Will foundations finance positions? Will candidates maintain employment with institutions whose interests may come before the board? What happens when the capitalist comes calling, and the union contracts come forth?
These questions do not establish wrongdoing. They establish the need for transparency.
Every candidate should disclose relevant financial relationships, potential conflicts of interest, outside employment, and arrangements that could influence the performance of public duties. Will Biggs join her husband at a foundation? Or will Hilario teach?
Chicago has seen enough political arrangements where the public title is only part of the story and the real power operates behind closed doors.
The voters deserve to know who is financing the politics surrounding their children.
Planatation Politics In A New Suit…
Plantation politics is not simply about race.
It is about control.
It is a political arrangement in which powerful institutions decide who receives resources, who gets a seat at the table, who is rewarded for cooperation, and who is punished for independence.
It is a system that welcomes Black participation but becomes uncomfortable when Black communities insist on independence.
That is the historical lesson of Harold Washington’s campaign. The lesson is that capitalists are comfortable with benevolent financing but not with financial support for empowerment. Its a painful lesson.
His supporters understood that political freedom was incomplete without the ability to organize and finance action.
Today, Chicago must examine whether the same dynamics are operating in public education.
Are wealthy donors and powerful organizations investing in better schools, or are they investing in influence over the people who govern them?
Are Black elected officials exercising independent judgment, or are they responding to political pressures from organizations with their own agendas to fund their own political efforts?
And where are the parents in all of this?
Where are the students?
Where are the teachers who simply want the resources to teach?
Where are the taxpayers who finance the system?
We hear plenty about the political organizations. We hear far less about the children.
Where Is The Leadership?
In 1983, Rev. Jesse Jackson and Operation PUSH helped create a place where political strategy, economic power, civil rights, and community organizing could meet. That place has dwindled without his towering presence and compelling voice.
Chicago needs that kind of independent civic conversation again.
We need organizations willing to convene the community, challenge established power, register voters, demand answers, and insist that public education remain a public trust.
The answer cannot be blind loyalty to a candidate because of race.
Nor can it be automatic loyalty to a union, political party, billionaire, or elected official.
The answer must be independent judgment, transparent financing, measurable educational goals, and genuine accountability.
Harold Washington‘s campaign taught Chicago that political power is not given. It is organized.
The new school board election offers a chance to ask whether that lesson has been forgotten.
Have we created a new era of parent and community representation?
Or have we simply created a new politics, a new patronage system, and a new set of power brokers between the union bosses and the capitalists?
The buildings belong to the public. The money belongs to the taxpayers. The future belongs to the children. The voice belongs to the parents and the community.
And the power must belong to the people.
That is the real test of this historic election.
Are we electing a school board—or choosing who controls the plantation?
