I've been meaning to write this...

I've been meaning to post this for sometime. I hate Chicago. Like there is a raw, simmering disdain that bubbles up whenever I think of Chicago—a name that conjures not just the sprawling metropolis by the lake, but something more insidious, a figure of betrayal and brute force wrapped in false charm. It’s like that moment in the only Black road trip romance film, Poetic Justice, where the air thickens with unspoken grievances and the miles stretch out like a test of endurance. Lucky, the quiet postal worker with dreams tucked away in his rhymes, finds himself tangled in a mess not of his making. Chicago, the loudmouth boyfriend tagging along, starts off as just another co-worker, but soon reveals his true colors: jealous, volatile, ready to lash out at the slightest provocation. When he turns on his then girlfriend, Iesha, his fists flying in a haze of alcohol and insecurity, it’s Lucky who steps in, delivering a knockout blow that leaves Chicago sprawled in the dust. They drive off without him, the group fractured but freer for it. In that moment, Lucky’s hate isn’t screamed from the rooftops; it’s in the decisive swing, the abandonment, the silent vow to never look back. Chicago becomes the embodiment of everything toxic—possessive, destructive, a drag on progress.

But peel back the layers, and that cinematic grudge mirrors something deeper, a metaphor for the Windy City’s own underbelly, where power brokers play the same abusive game on a grander scale. Chicago the city, with its gleaming skyline piercing the Midwest sky, hides a legacy of corruption that rivals any Hollywood script. It’s a place where politicians promise reform but deliver scandals, where the machine hums with bribes, kickbacks, and backroom deals that siphon the lifeblood from its people. These figures aren’t mere opportunists; they are architects of a self-sustaining edifice of graft, each one’s blueprint complementing the others’, ensuring the structure stands tall against reform. Take Michael Madigan, the long-reigning Speaker of the Illinois House, whose iron grip on state politics spanned nearly four decades until a federal jury nailed him on 10 counts of corruption in 2025, exposing a web of racketeering and bribery that funneled jobs and contracts to cronies. His state-level empire dovetailed seamlessly with that of Ed Burke, the powerful former Alderman who held sway over the city’s finance committee for decades, convicted in 2023 on 13 counts of racketeering, bribery, and extortion for shaking down businesses seeking city approvals; he served less than 10 months of a two-year sentence before release in July 2025, all while married to Anne Burke, a former Illinois Supreme Court Justice who retired in 2022 amid questions of conflicts of interest. Together, Madigan and Burke embodied the old Chicago machine, their corrupt networks interlocking like steel girders—Madigan pulling legislative strings while Burke enforced local dominance, as revealed in secret recordings and overlapping federal probes that painted them as mutual enablers in a culture of favoritism and payoffs. Or Rod Blagojevich, the former governor who tried to sell Barack Obama’s Senate seat like it was a flea market bargain, only to end up in prison after his 2008 arrest, his anti-corruption campaign pledge revealed as the hollowest of jokes. These aren’t isolated villains; they’re part of a dishonor roll that stretches back generations, from George Ryan, another governor locked up for graft, to the parade of Chicago aldermen—over 30 convicted between 1970 and 2010 alone—for everything from extortion to ghost payrolls. Layer in Jesse Jackson Jr., the former Congressman whose ambitions were woven into the fabric of Chicago’s political dynasty as the son of civil rights icon Jesse Jackson; he pleaded guilty in 2013 to conspiracy and fraud for looting $750,000 in campaign funds on luxuries like a Rolex watch and fur coats, serving time before announcing in October 2025 a bid to return to Congress—proving the revolving door spins eternally, bolstered by the machine’s tolerance for comebacks. Even his campaign treasurer, Chicago lawyer Vickie Pasley, faced a $7,150 FEC fine in 2013 for failing to file required reports amid the scandal, yet she continues to serve as an approved guardian ad litem in Cook County family courts as of 2025, handling sensitive child custody cases despite her past entanglement in political malfeasance—illustrating how enablers slip back into positions of trust, shoring up the system’s weak points. And now, enter current Mayor Brandon Johnson, elected on promises of progressive change, yet pushing a 2026 budget proposal laden with a controversial $21-per-employee monthly head tax on large businesses—framed as a levy on "job creators" that critics argue would drive companies away, exacerbate unemployment, and deepen the city's $1.2 billion shortfall, even as it faced rejection by the City Council's Finance Committee in November 2025 amid warnings from business leaders of economic fallout.

This architectural complementarity—where Madigan’s legislative fortress buttresses Burke’s municipal stronghold, and figures like Jackson Jr. navigate the corridors built by their predecessors, with aides like Pasley patching the cracks—is emblematic of how corruption perpetuates itself in Chicago. Each “architect” adds a layer that reinforces the whole, creating an impenetrable tower of influence that withstands scandals and investigations, much like the city’s iconic skyscrapers defy the winds off Lake Michigan.

This hate for Chicago isn’t born of ignorance; it’s forged in the fire of repeated betrayals. Just as Lucky saw through the facade of his road-trip antagonist, witnessing the harm inflicted on those around him, so too do the residents of the real Chicago grapple with leaders who assault the public trust. The city’s political machine, infamous for its unchecked power, breeds corruption like a virus—aldermanic privilege allowing council members to wield near-absolute control over zoning and development in their wards, often leading to pay-to-play schemes that favor the connected over the common good. Illinois ranks as the second-most corrupt state in the nation, with federal probes in 2022 targeting a slew of officials and costing citizens an estimated $550 million in lost economic activity. It’s a cycle of abuse: promises of equity and progress shattered by indictments, leaving neighborhoods underserved, schools underfunded, and infrastructure crumbling while the elite line their pockets.

Yet, in hating Chicago, there’s a reluctant acknowledgment of its potential—the flashing-lights of the nights, the architectural wonders, the resilient spirit of its people. Lucky, after all, moves on from the fight, finding solace in his music and family, hinting that redemption is possible if the toxic elements are cast aside. Similarly, the city could shed its corrupt skin through reforms like stronger ethics laws, independent oversight, and term limits to dismantle the entrenched power structures. But until then, the hate lingers, a poetic justice of its own, demanding accountability from those who treat public office like a personal fiefdom. Chicago, in all its forms—the character, the city, the symbol—stands as a cautionary tale: unchecked ego and greed will always invite a reckoning, whether from a fed-up postal worker or a weary electorate. I hate Chicago, not for what it is, but for what it allows itself to become.