Chicago is a city of great pride. Its residents wear the badge of resilience, overcoming decades of economic, social, and political upheaval. As a city that has been the epicenter of industry, culture, and innovation for more than a century, Chicagoans know they stand on the shoulders of giants. But today, there’s no avoiding the glaring truth: Chicago has a problem. It’s a problem that isn’t easily quantified or reduced to simple sound bites. This problem lies in the systemic failures that underpin the city’s crime, education system, and political machine. It’s rooted in deep inequality, corruption, and a widening gap between those who serve and those who are served.
This problem doesn’t just affect one neighborhood or one demographic—it touches everyone. And while the numbers might suggest that progress is being made, the lived reality of many Chicagoans paints a different picture. Crime statistics are down. Yet, as Illinois State Representative La Shawn Ford (8th District) candidly puts it, "How could we celebrate crime being down? There’s nothing to celebrate. People are still getting killed."
The problem is that, for many, there is no sense of safety, no sense of equity, and no clear path to accountability. Chicago’s issues go beyond headlines. They dig deep into a political system that prioritizes the needs of the few over the many, and into an educational system that fails to deliver on its most basic promise: to educate all children, regardless of their zip code.
An Education System Failing Its Promise
Michelle Pierre, a candidate running for Chicago's 1st District school board seat, is one of the voices fighting to bring attention to the dire state of the city’s education system. As someone with an extensive background in education—having served as a teacher, principal, and chief academic officer—Pierre isn’t just speaking from theory. She’s lived the dysfunction from the inside out.
"When only three out of ten kids can read, is that a good return on our investment?" she asks, pointing out the critical need for budget transparency and accountability. Pierre’s candidacy is built on three pillars: budget transparency, school choice, and giving communities a voice in how their schools are run. It’s a clear rebuke of a school system that many feel has long ignored the needs of its most vulnerable students. "I want to see where our funding is going," she insists. "We need to get a return on investment in our children."
But the problems in Chicago’s schools aren’t limited to funding. Pierre also highlights the deeper issue of political interference and how it seeps into decision-making at every level. A self-described independent voice, Pierre has faced smear campaigns simply for refusing to align with powerful groups like the Chicago Teachers Union (CTU).
"They blatantly created a lie ... and then we wonder why our city can’t get it together. It’s because of these politics," she explains. Pierre is frustrated but unwavering in her commitment to giving parents and students more control over their educational futures.
The school board elections have taken on new significance under Chicago’s Mayor Brandon Johnson, whose administration has been met with both anticipation and criticism. Pierre acknowledges that the mayor has influence, but she’s firm in her belief that the school board should be truly independent. She adds, "The mayor may have the ability to appoint, but we need real accountability from those in power. It shouldn’t be about politics—it should be about kids."
The Political Machine That Won’t Die
Jeanette Taylor, alderwoman for the South Side's 20th Ward, puts it bluntly: “We’ve always had a political machine problem. It’s Republicans against Democrats, unions against politicians, and everyone is beholden to who funds them.” Her words reflect a long-standing truth about Chicago’s political landscape—power is concentrated in the hands of a few, and those hands often belong to people who aren’t truly accountable to the communities they claim to serve.
While Taylor has been a vocal supporter of some of Mayor Johnson’s policies, she doesn’t shy away from critiquing him when it’s warranted. For example, she openly opposed Johnson’s decision to rehire Pedro Martinez as Chicago Public Schools CEO, saying, “I told him not to rehire Pedro in the first place. Look at how Black students are doing since the pandemic. Where's the accountability for how they spent COVID money?" Taylor is deeply frustrated with the lack of progress in improving outcomes for Black students, and her comments reflect a wider skepticism toward the mayor’s handling of the school system.
In Taylor’s view, the migrant crisis in the city also reflects the broader dysfunction of Chicago’s political leadership, including Johnson’s administration. "This was handled badly from the get-go," she says, referencing the city’s chaotic response to the influx of migrants. "It started off wrong. Remember, this was the Lightfoot administration telling the governor of Texas to kiss her, and he said, ‘Alright, I’ll kiss it. Take these migrants.’"
Taylor’s frustration is palpable as she talks about how entrenched political interests pit communities against each other. "I hate that we’ve gotten into this back-and-forth, Blacks against Latinos," she says. "We fought for years not to do that." In her ward, which includes neighborhoods like Back of the Yards and New City, racial tensions have become a destructive force, fueled by years of inequity and neglect. She emphasizes that this division is a direct result of Chicago’s broken political system, where elected officials are more concerned with their political allegiances than with the well-being of their constituents.
Taylor’s frustrations echo a larger sentiment shared by many in Chicago: a deep disillusionment with political leadership that promises change but too often delivers more of the same.
Crime: A Symptom, Not the Root
Crime in Chicago is often the headline story, but those closest to the problem understand that it’s merely a symptom of a much larger issue. Ford, the state representative who is a vocal advocate for equity, explains it best: "You can’t nibble around the edges."
"The only way we’re going to start improving the city is through equity across the board—in schools, jobs, police protection, and city services," he said.
Without equity, the disparities that fuel violence and crime will only grow larger.
While recent statistics show a decrease in crime rates, Ford is quick to point out that numbers don’t tell the full story. "There’s no way to celebrate when people are still getting killed," he says. The fact remains that many Chicagoans don’t feel safer, despite what the numbers might say. As Ford notes, "People still feel just as insecure as they did when crime was higher because it’s still happening." The focus on numbers, he suggests, allows city officials to deflect from the real issue—that the social fabric of the city is fraying due to deep-rooted inequality.
Ford’s critique of Mayor Johnson’s administration is not as direct as Taylor’s, but it’s clear that he sees the mayor’s office as needing to take stronger, more decisive action on the issue of equity. "The lack of equity creates all these other disparities," Ford explains, making it clear that unless Johnson prioritizes fairness in education, jobs, and public services, Chicago will continue to struggle with crime and social unrest.
Ford also touches on the importance of public engagement. "Politicians will do what voters say, but we have a problem with participation," he says. Without real civic engagement, he argues, leaders like Mayor Johnson will continue to make decisions without the accountability needed to address the city’s deeper problems. "If the communities that are well-organized stick together, they seem to do better."
The Way Forward
The themes that emerge from these conversations—inequality, political dysfunction, and public mistrust—paint a grim picture of a city struggling to live up to its potential. But what can be done? Each of the leaders interviewed for this story has their own ideas about the path forward, but they all share a common belief: change will only come through genuine accountability and community engagement.
For Pierre, the school board candidate, the answer lies in creating greater transparency in how resources are allocated, particularly in the education system. She advocates for giving parents more choice and ensuring that the city’s investments in schools are directly tied to student outcomes. "We need to stop raising property taxes without getting a return on investment," she asserts, emphasizing the need for a more efficient and results-driven approach to public education.
Alderwoman Taylor, meanwhile, stresses the importance of rebuilding trust between elected officials and the communities they serve. "What are you doing for your people?" she asks pointedly, calling on her colleagues to move beyond empty rhetoric and focus on delivering tangible results. For Taylor, the key to addressing Chicago’s issues lies in fostering unity rather than division—both within City Hall and across the city’s diverse neighborhoods.
And for Ford, the solution is equity, plain and simple. "The lack of equity creates all these other disparities," he says. Whether it’s education, employment, or public safety, Ford believes that only by ensuring fairness across the board can Chicago hope to solve its most pressing problems.
At the end of the day, what these conversations reveal is that the Chicago problem is systemic. It’s a problem rooted in political corruption, social division, and a lack of accountability. But it’s also a problem that can be solved—if the city’s leaders, and its citizens, are willing to face it head-on. As Pierre, so aptly puts it, "We can do better. And I’m going to keep fighting until we do."