Chicago’s Corruption Dynasty: The Daley Machine’s Destruction and Its Living Legacy

Editor’s Note

The following is a firsthand opinion/memoir piece by the author, written in her personal capacity. At F’nAround, we stand for truth and transparency. That’s why we are proud to publish this exposé on the Daley political machine and Chicago corruption without changing a word. It draws on the author’s firsthand experience and interpretation of events, and we support their first amendment right and decision to share it. We have ensured that every factual assertion in the piece is backed by the public record, and any personal viewpoints or conclusions are clearly presented as the author’s own protected opinion. To be clear, no sentence in the article should be misconstrued as a false assertion of fact. Our commitment to truth-telling and transparency is unwavering, and we stand firmly behind the publication of this story or any other we post.

Author’s Note

Power is a family tradition in Chicago—often passed down like an heirloom. I would know. My life was entwined with two of the city’s storied dynasties: the Daley’s and the Tribbett’s. I moved among Chicago’s elite from an early age, splitting time between City Hall’s backrooms and the private parlors of the “who’s who.” The halls of government and the corridors of influence were not distant institutions to me but the backdrop of my family gatherings and professional life. It was assumed I would someday claim my place in that world of clout and privilege, an unspoken inheritance of influence.

Yet I turned my back on that inheritance. Instead of embracing the “Machine,” as many local Chicagoans call it, I walked away from it. I write to you now as “The Rose,” a witness who grew from within Chicago’s Garden of Power but refused to be pruned by it. This exposé is my testimony—a blend of memoir and op-ed—rooted in lived experience and sharpened by public record. I am a daughter of Chicago’s political circle who chose to defect, and that decision grants me a unique lens on the Truth. I won’t deny: “Chicago politics” evokes images of smoke-filled rooms, stolen elections, and flagrant corruption​ chicagodetours.com. Much of it isn’t just imagery or legend; it was the reality I saw. I spent years watching deals being cut over steak dinners at La Scarola, Café Bionda, Tavern on Rush, Gibson’s, Hugo’s, Como Inn, Caffé La Scala, the mob-infested private clubs on Grand and Morgan, and many other infamous haunts, and promises traded behind closed doors. I know the weight of first names like “Richie” and “Maggie,” and I recognized early on that loyalty often trumped law and order in those circles. This is the story of what I saw—and how it frames the headlines everyone else has read.

In recent years, the very machine I once stood next to has begun to crumble under its own corrupt weight. A Daley heir—once presumed untouchable—was found guilty on federal fraud charges, marking a stunning fall from grace within the city’s first family davebyrnes29.journoportfolio.com. Chicago’s longest-serving alderman, Ed Burke, ended his career in disgrace, sentenced to prison after a decades-long reigndavebyrnes29.journoportfolio.com. I remember when my longtime childhood boyfriend, John Thomas Donovan, a strong Burke supporter, I will explain why later in the series, used to explain the benefits of patronage to me in our ivy league level Jesuit high school, called Saint Ignatius College Prep, that resembled the halls of a modern-day ultra-exclusive Hogwarts. Longtime pillars of the old order, from the Burke and Cullerton clans to lesser-known power brokers, have faced indictments and convictions. I remember when Senator Cullerton, brokered by his son Garritt Cullerton, took me to a real estate meeting with Ed Burke at his aldermanic office during his corruption trial. We will get into this mind-blowing exchange later.

These events might sound unbelievable to anyone who grew up on tales of the Daley machine’s invincibility. But they happened in plain view, documented by courts, and covered in the news. In fact, more than 1,500 public officials in Illinois (including dozens from Chicago) were convicted of corruption from 1970 to 2010 alone​ wttw.com. The dynasty of Chicago corruption was not just a metaphor—it was a generational reality that is now being dismantled case by case. As a former darling, I see these developments not with shock but with a knowing nod. The fall of these figures is the inevitable consequence of a system that I witnessed operating with impunity for far too long.

And yet, even in destruction, a dynasty leaves behind its legacy. Chicago’s political landscape still bears the imprint of the Daley era and the circles of influence that orbited it. The machine’s living legacy is all around us: in the institutions and contracts shaped by decades of patronage, in the wary cynicism of Chicago’s electorate, and in the protégés of those old bosses who still walk the halls of power. The names on the office doors may have changed, but many of the game's rules remain unwritten and familiar. I often recognize strategies and echoes of rhetoric—faint ghosts of the Machine—in today’s city council debates and election campaigns.

This series is not just about looking back at how the Daley machine rose and fell; it’s about understanding how its spirit endures in 2025. Even as new reformers try to turn the page, the story I must tell reminds us that history lingers and oftentimes repeats itself if we are not careful. The same culture of loyalty and leverage that built Chicago’s corruption dynasty still whispers in the wings of the stage, reminding us that old habits die hard.

Let me be clear: I speak only the truth as I know it and do so confidently, without apologizing. But I also speak responsibly. Every public figure and family I reference—be it the Daley’s, the Tribbett’s, or any other—will be mentioned in the context of facts on the public record. There is no need (and no intent) to traffic in rumors or sling mud beyond what evidence and history support. Where corruption is alleged, I will note it as allegation; where it is proven, I will state it as fact with proof in hand. This is my story of navigating a city long branded America’s corruption capital​ wttw.com, intertwined with Chicago’s story of self-destruction and survival. It’s a personal narrative, protected as opinion, but it’s bolstered by hard truths that have already been laid bare in indictments, courtrooms, and headlines. I write with a fearless voice—poetic at times, yes, but always grounded in reality. My aim is to expose wrongdoing as I saw it, not to defame but to illuminate the dark corners of Chicago’s political past so that we might finally clean them out. If that requires piercing the comfortable silence that surrounded Chicago’s ruling class, so be it. I was there. I have the receipts, both literally and figuratively, and I refuse to stay quiet. Reflecting on the words of a respected and renowned colleague who oncetexted me, “Some people spill the tea. Brittini Flatley brings a whole freaking jug.” And with that, I must tell the whole Truth and nothing but the truth as I can remember it.

Therefore, I thank all those countless souls who quietly aided me and mine as the weight of the Machine and its allies intentionally, strategically, and consistently attempted to crush me financially, professionally, personally, emotionally, physically, and mentally over countless years, thank you for lighting the flame so I could find my way out of the tunnel. And with that, we shall begin.

Chicago’s Corruption Dynasty: The Daley Machine’s Destruction and Its Living Legacy

“Chicago’s Corruption Dynasty: The Daley Machine’s Destruction and Its Living Legacy” is a multi-part journey. This introduction is merely the first step, a scene-setter frommy perspective. I symbolize myself as The Rose because Ihad a front-row seat to power and chose conscience over inheritance. In the chapters to come, I will guide you through the rise and fall of the Daley empire as only an insider-turned-outsider can. Think of it as a guided tour behind the velvet curtains of Chicago’s political theater—one part history lesson, one part personal catharsis. By the end, you’ll see not only how the mighty fell but how their influence persists and what that means for the future of our city.

A memoir.

By: Brittini Flatley/AI (for fast fact-checking purposes)  

Former Mayor Richard M. Daley, son of the infamous Richard J. Daley, speaks at an event in 2007. The Daley political machine shaped Chicago for decades with iron-fisted control and systemic corruption.

Half a century ago, legendary columnist Mike Royko pulled back the curtain on Mayor Richard J. Daley’s reign in his book Boss. Royko dubbed Daley “the last of the big city bosses,” a leader who wielded near-absolute power over Chicago’s politics en.wikipedia.org. Daley’s machine was a well-oiled empire of patronage jobs, favors, and fear. It paved asphalt and plowed snow efficiently – “evil… but efficient,” as Royko implied​commentary.org – yet it poisoned the city's soul. Royko observed that under Daley, Chicago was run “not in the corporate style... but rather as if it were a highly successful family business”​ commentary.org. And indeed, it was. The Daley family turned public service into a private enterprise, tightly controlling an “evil machine” within an “evil system” commentary.org that rewarded loyalty, punished dissent, and treated the city like its fiefdom.

The Daley Machine: Power, Corruption, and Collateral Damage

Royko’s portrait of mid-century Chicago described a city government rife with graft and brutality. In Daley’s Chicago, “police corruption [was] pervasive” – cops on the take, suspects beaten and robbed – yet most Chicagoans accepted it “as a natural part of Chicago”​ bookrags.com. This was the cost of the Daley order: services delivered, trains that “run on time” under a boss-like mayor​ commentary.org, in exchange for turning a blind eye to graft and violence. This trade-off persisted under both Richard J. Daley and his son Richard M. Daley. Patronage armies won elections while police torture and misconduct were swept under the rug. (In fact, then-State’s Attorney Richard M. Daley was informed in the 1980s of egregious CPD torture allegations and did nothing – an omission that would later haunt him in court​ cbsnews.com, peopleslawoffice.com.) The Daley machine’s “laissez-faire policy toward corruption”​ goodreads.com fortified a culture where bosses thrived and regular people suffered.

The human toll was real. Generations of Black and brown Chicagoans bore the brunt of this corruption-fueled regime – from police abuses to the systemic neglect of neighborhoods not aligned with the machine. Even as Richard J. Daley infamously proclaimed, “The police are not here to create disorder, they’re here to preserve disorder,” his administration tacitly encouraged chaos in marginalized communities while protecting loyal wards. The 1968 Democratic Convention crackdown, the wrongful convictions tied to police torture, the 1,828 Illinois corruption convictions in the decades after Daley’s deathelearning.ndu.edu.ng – all these injustices trace back to a power structure that valued clout over citizens.

Meanwhile, the Daley clan and their cronies feasted. Scandals punctuated Daley rule like a drumbeat. In the Hired Truck Program scandal, the Sun-Times revealed how mayoral cronies and even Mob-linked contractors, similar to Rooney, Marchese, Duffy, Rogers, Johnson-Rice, Mell Mell Meowed on Blago, and more friends-help-friends-raise-funds were getting fat off a $40 million city trucking scheme – paid for doing little or no workchicagomag.com. City funds were siphoned to sham minority-owned companies run by white pals of the machine. The scheme checked every corruption box: waste, fraud, favoritism, abuse of minority-business programs, and nepotism (one of Daley’s brothers, John Daley, even provided insurance to the trucking companies) chicagomag.com. Richard M. Daley professed shock – “I am embarrassed, I’m angry… I feel I have let the people down,” he said, even appearing to choke up​chicagomag.com– but the tears rang hollow. This was his machine at work. One investigative report noted thatDaley had “tolerated a corrupt program that wasted… tens of millions of taxpayer dollars”​chicagomag.com. Time and again, Daley would apologize for scandals but never truly dismantle the system that spawned them. After all, that system kept him in power. Favoritism and self-dealing were not bugs of the Daley machine; they were features. Under Richard M. Daley’s 22-year mayoralty, “family, personal friends, and political allies disproportionately benefited from city contracting”​ en.wikipedia.org, as documented by the Chicago Tribune. City Hall became a piggy bank for those with the right last names and connections. Daley’s relatives and loyalists landed lucrative deals – until the feds or the press caught on, and a low-level fall guy took the blame. The Daley administration perfected the art of plausible deniability: the boss claimedignorance while his inner circle ran wild. When caught, Daley would fire an aide, commission a report, and declare the problem solved – even as the “Chinese water torture” of scandal after scandal continued to drip out​ chicagomag.com.

Consider just a few examples of how the Daley dynasty weaponized Chicago’s institutions for profit and power:

• City Contracts and Nepotism: From trucking to trash pickup, contracts flowed to machine-favored firms. One infamous example: Mayor Daley’s nephew Robert Vanecko and a top ally, Allison Davis (a developer and Daley donor), convinced five city employee pension funds to invest $68 million with them. Over the next few years,they lost 80% of that money – $54 million vaporized – by sinking it into risky real estate deals​chicago.suntimes.com. Yet Vanecko and his partner still collected about $9 million in management fees for themselves​ chicago.suntimes.com, chicago.suntimes.com. In other words, the Daley relative got rich while city workers’ retirements suffered. (Daley later claimed it was “not a good decision” to involve his nephew​abc7chicago.com– a rare admission of fault.) This brazen nepotism was Chicago Machine Politics 101: heads, the insiders win; tails, the taxpayers lose.

• Mob Ties and “Legitimate” Thugs: The Chicago Outfit and the Daley machine had a long, incestuous relationship. For years, John F. Duff Jr., a politically connected union boss and staunch Daley supporter, acted as a bridge between City Hall and organized crime. Duff had “strong ties to [the] Outfit” – he was friends with mob boss Tony Accardo – and he helped run sham minority-owned firms that grabbed millions in city contracts​ illinoisanswers.org, illinoisanswers.org. One of Duff’s companies famously provided janitors for city festivals, overbilling taxpayers outrageously while flaunting clout. When the Duffs were finally busted for minority-contract fraud in the 2000s, Daley claimed he hardly knew them. But FBI files showed the elder Duff had been a City Hall insider since the first Mayor Daley’s time illinoisanswers.org. The Duff saga was a microcosm of the Daley era: mobsters in business suits, profiting off public programs under the guise of legitimate business, all while rubbing elbows with the mayor. As a Daley spokesperson blandly put it when pressed on these unsavory allies: “After 22 years at the helm of a city as mayor, you know a lot of people”​illinoisanswers.org. Indeed, you do.

• Financial “Blunders” That Bled the City: In Daley’s final term, desperate to paper over budget shortfalls of his own making, he did the unthinkable – he sold off Chicago’s future. In 2008, Mayor Richard M. Daley rammed through the notorious 75-year parking meter lease, handing control of every Chicago parking meter to a private Wall Street-led syndicate for an immediate $1.15 billion cash payout​fox32chicago.com. It was a fire sale price: the city’s meters make so much money that the investors are projected to recoup their entire payment in just 15 years, after which Chicagoans will still be feeding those meters (and private pockets) for 60 more years​ fox32chicago.com. Daley gave away a revenue stream through 2083 – and with it, a chunk of the city’s sovereignty – to plug a short-term hole in 2009. “One of the city’s biggest blunders” doesn’t begin to describe it​ fox32chicago.com. Critics rightly call it one of the worst public privatization deals in American history. The 75-year meter lease, rushed through the City Council with barely any scrutiny (approved 40-5 with many aldermen not even reading it), epitomized how the machine operated at its cynical worst​ fox32chicago.com. Daley bet that Chicagoans wouldn’t notice the future being pawned off – and by the time they did, he’d be comfortably retired. Today, the city is still reeling private investors laugh all the way to the bank as Chicago’s parking rates soar, while the “quick fix” $1.15B has long since been spent. As the Civic Federation’s watchdog later lamented, Chicago “gave up a major moneymaker” and got nothing lasting in returnfox32chicago.com. This was governance by short-term greed, and its consequences – chronic deficits, higher fees, public distrust – are the Daley legacy Chicagoans inherit.From the 1950s through the 2000s, the Daley name was virtually synonymous with Chicago power. Richard J. Daley ruled for 21 years, Richard M. for 22 – together, father and son sat atop City Hall for over four decades. In that time, they built a formidable patronage network that permeated every branch of government. Precinct captains got city jobs for loyal voters; judgeships and contracts were awarded to friends of the Machine. Springfield (Illinois’ capital) danced to Chicago’s tune as Daley-allied legislators and lobbyists greased the wheels. Even the Vatican and the Archdiocese had their part in this web: as devout Irish Catholics, the Daley’s enjoyed the Church’s imprimatur. Cardinal John Cody and other Catholic leaders gladly bestowed blessings on the Daley regime, lending moral cover to a very amoral enterprise. Private Catholic schools and charities benefited from Daley patronage, and in turn the Church hierarchy often stayed mum on City Hall’s sins. It was an old bargain, harkening back to the city’s first ward bosses who doled out coal and jobs through the parishes. In Chicago, the line between the “Cathedral and the Machine” was thin: both were pillars of the Irish community’s rise. The result was a quasi-feudal arrangement – a city where political, business, and religious elites formed one interlocking directorate, accountable only to each other.

The Dynasty’s Heirs and Allies: A Network That Never Died

When Richard M. Daley finally stepped down in 2011, many hoped Chicago might at last exorcise the ghost of the Machine. But the Daley dynasty was not so easily vanquished. Like a hydra, it sprouted new heads. Even out of office, the Daleysand their allies quietly maintain a stranglehold on key institutions. John P. Daley, Richard J.’s son (and Richie’s brother), remains a powerful Cook County Commissioner and Democratic committeeman, still chairing the county’s finance committee after decades. Patrick Daley Thompson, Richard J.’s grandson (and Richard M.’s nephew), comfortably won the old family aldermanic seat in Bridgeport – until he was convicted in 2022 on tax fraud charges for lying about a dubious $219,000 loan, he received from a bank that later collapsed in fraud​ fox32chicago.com, fox32chicago.com. (In true Machine fashion, Thompson recently got two of those convictions overturned on appeal​ fox32chicago.com– clout dies hard.) Richard M.’s brother William “Bill” Daley parlayed the family name into roles as U.S. Commerce Secretary and White House Chief of Staff, and even mounted a well-funded campaign for mayor in 2019, coming in third​ politico.com. And what of the Daley women – the behind-the-scenes pillars of the clan? The late Maggie Daley, Richard M.’s wife, was known as “Chicago’s First Lady” and ran charitable initiatives that boosted City Hall’s image. Daley’s daughters Nora Daley and Elizabeth Daley (and his nieces and in-laws like Christine, Maura, and others) continue to move in the city’s elite circles – chairing cultural boards, leading foundations, investing in businesses – quietly leveraging the family legacy. In Chicago’s boardrooms and clubrooms, the Daley influence endures. It’s in the air at the University Club, in the deals cut at Gibsons steakhouse, at St. Ignatius prep’s alumni dinners. The names might not always be Daley – some have married into names like Martino, Vanecko, Joyce – but the bloodline and the influence remain.

Crucially, the Daley’s long ago seeded a broader network of allied families and loyalists to carry on their machine. Think of it as Chicago’s shadow dynasties – clannish, immensely wealthy or well-connected families who have profited alongside the Daley’s and buttressed their rule. These families form a who’s-who of Chicago power: the Pritzker’s, the billionaire clan behind Hyatt hotels and led by Gov. J.B. Pritzker, who epitomize the marriage of money and politics; the Crowns, heirs to an industrial fortune and major civic players (their name adorns the Crown Fountain in Daley’s Millennium Park, a testament to cozy public-private collaboration); the Polk’s and McCormick’s, old-money families whose philanthropy often aligns with City Hall interests; and newer influential players like the Cabrera’s and Connolly’s, minority and ethnic power brokers brought into the fold to broaden the machine’s reach. Under Daley’s big tent, these families found common cause. They traded favors, sat on each other’s boards, greased each other’s deals. For example, financier Martin Cabrera Jr. – a Latino business leader and Emanuel appointee often aligned with Daley interests – helped broker a $3.6 million city grant to a bank in 2012, only to personally receive $700,000 in loans from that same bank shortly afterchicago.suntimes.com, chicago.suntimes.com. Such reciprocal backscratching between City Hall and business insiders has been standard practice. Likewise, political fixer, often confused with the title Silent Kingmaker, Charles Tribbett III (of the Tribbett family) has been a behind-the-scenes force, raising piles of cash for Daley campaigns​ politico.com and greasing the wheels between Illinois politicians and corporate giants.

This extended Machine 2.0 doesn’t always flash the Daley name, but it operates with Daley DNA. It’s the reason why, long after a Daley last sat in the mayor’s chair, Chicago can still feel like a city controlled by a select few intertwined clans. These power families have turned city government, education, development, and even charity into a closed-loop system serving their interests. They leverage institutions at will: the Chicago Police Department (historically used to shield the powerful and intimidate inconvenient voices), the Cook County Courts (where judges owe their robes to machine backing), the state legislature in Springfield (where machine-allied figures advance legislation benefiting Chicago’s insiders, whether it’s tax incentives or cannabis licenses). They even co-opt seemingly benign systems like parking enforcement or school admissions – consider how Chicago’s punitive parking ticket and towing system functions as a regressive cash machine, hitting working-class residents hardest while connected insiders’profit from private contracts to run the system. Or how elite private schools (often Catholic-affiliated) quietly reserve spots for the offspring of clouted families, keeping the next generation’s networking exclusive. In Chicago, institutional mechanisms that should serve the public often end up weaponized to serve the Machine.

New Frontiers of Corruption: The Machine Adapts (Cannabis, Real Estate, and Beyond)

While the Daley era of mayoral rule is over, the model of Daley-style corruption is alive and evolving. In recent years, Illinois’ booming new industries – like legal cannabis and downtown real estate booms – have provided fertile ground for the Machine’s heirs and allies to flex their clout. What does a political machine do when the old rackets (like patronage hiring or hired trucks) get exposed? It finds new rackets. A stunning current example centers on Illinois’ cannabis industry, where a cast of Machine-tied players has appeared in the shadows. Joseph Phelan v. nuEra is a lawsuit that, in peeling back the layers of a business dispute, uncovers the same familiar network of influence and impunity.

nuEra Cannabis is one of Illinois’s major marijuana companies – officially a private business, but if you scratch the surface, you find the fingerprints of Chicago’s ruling class. Joseph Phelan, a financial entrepreneur, says he became a partner in nuEra only to be defrauded and frozen out when he wouldn’t play ball with corruption. According to Phelan’s account (now part of his lawsuit in Cook County Circuit Court), an insider bluntly told him that nuEra’s owners “own the state and [its] politicians”, boasting that they have so much clout “no one will touch them”​linkedin.com. In other words: the fix is in, from the Governor’s office on down. It’s a chilling statement – and it echoes exactly the kind of arrogance one would expect from a modern Machine that believes it’s untouchable. Phelan didn’t back down; instead, he went digging. What he found, he claims, is a hidden web connecting nuEra’s principals to high-level politicians, regulators, and yes, members of the Daley family.

In a recent public expose, Phelan revealed he had obtained recordings of conference calls involving nuEra executives and their investors. On those calls were a Who’s Who of clout: a Daley family member was present, as were government contractors, media figures, and even international financiers​linkedin.com. It was as if a mini “City Hall behind closed doors” was happening on these phone lines – with deals and strategies hashed out away from prying eyes. Phelan has since turned over troves of evidence to authorities and the court. His lawsuit, co-filed with U.S. Navy veteran Juan “Tony” Finch Jr., accuses nuEra’s CEO Bob Fitzsimmons and others of orchestrating a scheme to undermine Illinois’ social equity cannabis licensing. The details are eye-popping: nuEra (led by Fitzsimmons) allegedly funded and directed a legal challenge to Illinois’ Social Equity program, using Finch – a Black, LGBTQ veteran – as the front man “pawn” to sue the statenueraclassaction.com. The goal? To get the courts to strike down equity rules that prioritized cannabis licenses for communities harmed by the drug war, thereby protecting nuEra’s market share and delaying minority entrepreneurs from entering the market​ nueraclassaction.com. It was a cynical exploitation of the very people the equity law was meant to help. And for a time, it worked – the lawsuit caused long delays in the licensing process, effectively freezing out many minority applicants while companies like nuEra tightened their grip.

When Finch realized he’d been used – promised a dispensary license in exchange for lending his name to that suit, only to be cast aside – he joined forces with Phelan to blow the whistle​nueraclassaction.com. What they uncovered paints a picture of Illinois’ cannabis industry as the Daley machine in a new disguise. We have a powerful CEO (Fitzsimmons) with political friends, even in the Governor’s circle; we have the apparent involvement of a Daley relative (reminding us that the family never truly left the stage); and we have regulators and watchdogs who inexplicably failed to act. In fact, Phelan states that when he presented evidence of nuEra’s misconduct to oversight bodies, the Illinois Attorney Registration and Disciplinary Commission and even the Illinois Supreme Court “literally put in writing that they refuse to investigate,” ignoring what Phelan describes as felony-level offenses​ linkedin.com. That deafening silence from authorities is all too familiar in Chicago – it’s the sound of impunity. It harkens back to decades of Machine protection: the powerful protecting their own. If Phelan’s allegations are true, it means the Daley-era playbook of corruption has simply migrated into new arenas like cannabis and tech startups, where the faces are younger, but the game is the same.

The nuEra saga is still unfolding in court, but it has already lifted the veil on how Chicago’s hidden power structures adapt rather than disappear. Today’s Machine might swap out patronage clerks for investment portfolios, and precinct captains for LLCs and lobbyists, but its essence – a network of influence that operates above the law – persists. As Phelan quipped on social media, “the cover-up is worse than the crime”linkedin.com– a statement that could serve as an epitaph for so many Chicago scandals past and present. And as he continues to expose nuEra’s dealings, more names are likely to emerge, potentially linking Illinois’ billion-dollar cannabis market and even the booming real estate developments (where politically connected firms still get the sweetest deals) back to the same old crowd.

Conclusion: From the Ashes of the Machine, an Awakening

Chicago stands at a crossroads. The Daley family and their allies spent decades constructing a shadow empire that “destroyed the city’s systems and people” for their own gain – from public trust and finances to the very moral fabric of institutions. They were the poisoned roots of a great city, roots that strangled justice and equity. But by shining light on these hidden networks – by naming the names and mapping the connections – there is hope to break their grip. This exposé is not merely an indictment of one family, however powerful; it’s a call to recognize the patterns of corruption that have persisted across eras, and to finally demand the accountability that has long been deferred.

Chicago is often called the “City of Broad Shoulders,” built by hard-working people of every color and creed. Those shoulders have carried the weight of corruption for too long. Yet the truth is coming out. With each lawsuit, each investigation, each brave whistleblower like Phelan and Finch stepping up, the armor of invincibility around Chicago’s ruling class gets dented. Like Brittini Flatley – “The Rose” whose voice refuses to be silenced – we too must speak truth to power with fearless, poetic ferocity. We recall the words of Richard J. Daley’s most famous nemesis, civil rights leader Dr. Martin Luther King Jr., who said in Chicago in 1966 that he’d never seen mobs as hostile as those organized by Daley’s machine. That hostility was the dying gasp of an old order that knew its time was up. Today, a new generation of Chicagoans is awakening to the reality that the Machine never truly died in the 1970s or in 2011 – it only shapeshifted. And now, at last, its shadows are being illuminated.

This first chapter has pulled back the curtain on the Daley dynasty and its far-reaching web of corruption – from the patronage mills of the 1950s to the cannabis rackets of the 2020s. In the next installment of this exposé series, we will delve even deeper into that web. We will trace how these same power brokers infiltrate and exploit Chicago’s law enforcement, educational, and political systems today, and we’ll expose the specific allied families who have carried the Machine’s torch into the modern era. Names will be named. Secrets will be laid bare. The goal: to finally break the cycle of silence and enable Chicago to reclaim its government for the people.

Chicago’s story is not finished – a better future can be written, but only with open eyes and an unflinching commitment to justice. The Daley’s and their ilk wanted Chicagoans to believe corruption was as inevitable as winter snow. We reject that. With knowledge as our weapon and truth on our side, we can dismantle the machinery of corruption piece by piece. Stay tuned for the next chapter, where we continue to map the road from darkness into light​ linkedin.com, and together, inch closer to the day when Chicago’s “clout” is replaced by accountability, and its people are no longer pawns, but true stakeholders in the city they love. The revelations have only begun – and nothing, not even Chicago’s most entrenched interests, will stay hidden for long​ linkedin.com, linkedin.com.

Next installment, we continue our journey through Chicago’s halls of power and backrooms of deal-making, determined to finish what was started and finally give this city – our city – the honest, transparent governance it deserves. (To be continued.)

Sources:

• Royko, Mike. Boss: Richard J. Daley of Chicago. New York: Dutton, 1971. (as cited in Commentary Magazine)​commentary.org commentary.org

• Royko on police corruption in Chicago​ bookrags.com

• Cohen, Adam et al. “Daley’s machine legacy.” Encyclopedia of Chicago (Britannica)​en.wikipedia.org goodreads.com

• Spielman, Fran. “Daley and the Hired Truck Scandal.” Chicago Sun-Times, 2004​chicagomag.comchicagomag.com

• Novak, Tim. “Daley pension debacle: Where did $54 million go?” Chicago Sun-Times, Dec. 9, 2018​chicago.suntimes.com chicago.suntimes.com

• Illinois Answers / BGA. “FBI Files on Daley associate John Duff” (2011)​illinoisanswers.org illinoisanswers.org

• Supreme Court of the U.S. ruling on Patrick D. Thompson (Fox 32 News)​fox32chicago.com fox32chicago.com

• Kapos, Shia. “Money Spigot opens for Daley” Politico Illinois Playbook, Jan. 2, 2019,​politico.com

• Bergo, Sandy and Neubauer, Chuck. “Rahm crony helped bank in Manafort case get city grant…” Chicago Sun-Times/BGA, Aug. 3, 2018,​ chicago.suntimes.comchicago.suntimes.com

• “Chicago’s parking meter deal still haunts the city” (Fox 32 News)​ fox32chicago.com fox32chicago.com

• Brittini Flatley & Joseph Phelan, LinkedIn posts on NuEra lawsuit and corruption, 2024​ linkedin.com linkedin.com

• Phelan v. NuEra Cannabis – Issue Wire press release, Aug. 21, 2024,​ issuewire.com issuewire.comNueraclassaction.com press release​ nueraclassaction.com

• Illinois Supreme Court/ARDC correspondence (as quoted by Phelan)​ linkedin.com

• Various Chicago media archives and court documents, 2023-2025​ linkedin.com linkedin.com

Disclaimer

The views expressed here are the author’s own, based on her personal experiences and interpretation of publicly available information. All individuals mentioned should be considered innocent of any wrongdoing unless such wrongdoing has been proven in court. This piece is not intended as a formal accusation against any person but as commentary on matters of public interest.

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