Chicago’s Corruption Dynasty: All Roads Lead to Rome

Chicago’s Corruption Dynasty: All Roads Lead to Rome

A memoir.

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

A Childhood in the Church’s Shadow

I pen these words as both an opinion and a memoir – a tale of Chicago’s ruling class entwined with the silent power of the Vatican. My earliest memories unfold in the halls of Old St. Patrick’s preschool, where Sister Mary Ellen Carol’s (no longer a ‘Sister’ in the sense of a nun, but now the CEO of After School Matters) gentle voice taught obedience and quiet. I was too young to realize it then, but this Catholic institution was more than a place of learning; it was an indoctrination ground for Chicago’s elite. As a child, I met Cardinal Joseph Bernardin – a towering figure who loomed large over Chicago’s Catholics. I remember being ushered into neat lines to greet him at a fundraiser, all of us oblivious to the other truths cloaked in reverence. Years later, when disturbing allegations surfaced against Bernardin in the 1990s, Mayor Richard M. Daley publicly defended him, calling the claims “outrageous” ​latimes.com. It was a lesson I’d seen repeated: when powerful men in cassocks or suits faced scrutiny, the system closed ranks. My young mind absorbed that some people’s sins would always be “forgotten” – as Cardinal John Cody once wrote to reassure an accused priest that no good would come from investigating abuse claims ​cbsnews.com. In Chicago, faith and fear conspired to keep such scandals in the dark.

Growing up, I suppressed uneasy memories: the leering smile of a parish volunteer, the subtle racial hierarchies even among preschoolers, and the way Sister Mary Ellen’s praise always shone brightest on the children of donors, Daley’s, mafia-connected business owners, and aldermen. We were groomed to accept hierarchy – from kneeling before God to bowing to political royalty. For a long time, I chalked it up to tradition. Only later did I recognize it as cultural grooming: Know your place. Don’t speak out. Protect the powerful. These lessons weren’t in any catechism, but they were imparted all the same, woven into every morning and afternoon prayer and all school holiday pageants we would put on for the parents, friends, and family.

Catholic Institutions: Grooming the Next Elite

Chicago’s political Machine always had an ally in the archdiocese. The Daley dynasty, the Tribbett’s, the Rickett’s,Wrigley’s, Kovler’s, the Pritzker’s mjbizdaily.com —so many of the city’s enduring power brokers—either came up through or were tightly looped around the same Catholic circuits that I did. That closeness wasn’t always visible to the public, but in the pews, classrooms, fundraisers, and board appointments, we were all there—one way or another.

I remember once being sharply corrected by a family member—my uncle, Charles A. Tribbett III, a man with a measured, quietway of reminding people of their place. He told me flatly: “You didn’t go to private school. You went to a Catholic school. There’s a difference.” I was young, but even then, I understood what he meant: Latin School injusticewatch.org, where he sat on the board, and his children attended, and Francis Parker was for a different elite tier. But from where I stood, schools like Saint Ignatius College Prep charged tuition higher than the annual salary of many working families I knew. The distinction was real in the world of power and prestige—but so were the overlaps. We’ll get into that family dynamic later in this series. Honestly, it could be its own series. I’ll leave that call to the producers.

It’s no coincidence that Michael Madigan, the longtime Illinois House Speaker and architect of much of the state’s political chessboard, graduated from St. Ignatius and was a regular at daily Mass as a boy. Nor is it a coincidence that Thomas Donovan’s children, Grace and John, walked the same halls. Grace followed the pipeline—through Catholic schools—into the State’s Attorney’s Office, with a well-timed detour through Notre Dame. That Fighting Irish seal carries weight in certain circles.

They always thought John would be the one to follow that path, me too. But I suppose sometimes the apple doesn’t fall far from the tree—and other times, it doesn’t quite make it out of the orchard.

I remember one day in the school cafeteria as if it wereyesterday. Tommy Tully was mocking Grace about her seizures. I was one of the few who spoke up for her. I yelled, furious. Days later, Tully passed from a sudden brain issue. I still carry that moment—his words, my defense, his death—as a strange ghost in my memory. I didn’t know what to feel. But when people carry names tied to officers who’ve killed Black children in the street, like this one here Chicago Police Settlement Tracker, it’s hard to cry for lineage. It’s all connected.

Connected. Even now—almost forty years later, to Joseph Phelan’s, another Old St. Pat’s inaugural class, and St. Ignatius alumni like me cannabis fiasco. It makes me think of a recording we discussed regarding the Marc Realty family—another clan from my Ignatius orbit. The son, Tate. The father, Jerry. Alumni. They own hundreds of millions in real estate across Chicago.And yet, they recently asked Joseph Phelan, during active litigation and federal investigation, to meet in an abandoned building they controlled. Not for business—but to “talk.” During that meeting, they invoked ‘what used to happen near the river’ during the “Clinton days,” likening what would happen to him if he kept speaking out—a threat, not a metaphor.

That same Tate, while engaged, would roam the family's low-income buildings, telling needy families he’d pay their rent if their daughters came to him sexually. That story made its way through more than one building. Until one day, Tate got sick. Someone else came to collect the rent. That incident ended...quietly. I’ve seen Jerry fix bigger messes.

I also remember Anthony Conforti, introduced to me by Michael Daley—another Old St. Pat’s preschool classmate. Conforti is the son of a known Daley associate and a legacy real estate kingpin. I once toured a building with him that he planned to flip. His intention? To displace every resident inside—no notice, no support—so he could turn it into luxury condos. I remember thinking: Is this what funds your party-filled nights at Maple & Ash? chicago.eater.com

Yes, that Maple & Ash—the restaurant chain embroiled in legal controversy across Chicago and Scottsdale. The same tired story: boys-now-men fighting over stolen money, contracts, and fragile egos. Once described as “the highest-grossing restaurant in the city” wbez.org, Maple & Ash attracted silent powerhouse investors like Rossi and Cosich, to name a few. wbez.org

But what stuck with me wasn’t the greed—it was the cruelty.

Conforti once called me a “nigger” and a “stripper,” and circulated a modeling photo of me to Dick Mell and others in an attempt to discredit me during a time when I was struggling and deeply vulnerable.

Let me be clear: I have never been a stripper. I’ve never worked in a strip club, nor have I done half the things rumored about me. Over the years, I’ve learned that when people try to discredit or humiliate you, it’s often because they’re the ones doing something wrong. Gossip is projection. Malice is confession.

And I’ve also learned something else: small men will always try to reduce strong women to whores, sluts, or nobodies, hoping it will create some small fracture in our reputations—or our minds. Conforti wasn’t the first. But he will be the last.

Because through him, I finally learned the art of silence and the power of no. These days, I deny access to people like an overzealous bouncer at the hottest club in town. It’s liberating to realize you don’t owe anyone anything—not an explanation, not a version of your past, not even a response.

You're here to complete your journey. That’s it. If others walk with you, beautiful. But if not, be prepared—and content—to walk alone.

At times, people have tried to reduce me to an image. They’ve twisted my story, weaponized old modeling photos, spun narratives that had nothing to do with truth. But in the end, those judgments say more about them than they ever will about me.

I’m reminded of the 2001 song by City High, “What Would You Do?” It opens with a haunting question:

“What would you do if your son was at home, crying all alone on the bedroom floor 'cause he's hungry?
And the only way to feed him is to sleep with a man for a little bit of money?” 【City High, 2001】

That song hit different then—and now. Because even at my lowest, I didn’t cross that line. I’ve stared down eviction, repossession, debt, and complete financial collapse. I’ve lived days without electricity. I’ve had zero dollars in my account with two mouths to feed. But I never sold my body. Not even when I thought I had no other choice.

And I want to say thank you to those who bought groceries when my fridge was empty. Even if some of them did it with strings attached—knowing they’d try to cash in that favor later. It was my first introduction to the economy of political favors—a world where generosity is rarely free, and kindness is often currency. In the last five years, I’ve come to understand how deeply that trade-and-favor system runs. We’ll get into my days in Illinois politics later. Trust me, it deserves its own chapter.

Yes, I modeled. I acted. And yes, there was a time when I thought Playboy Live, Howard Stern-style sex content, and over-sexualized modeling might fill the emptiness I carried. I was wrong. Later in life, I realized only I could do that—only I could love and free myself. I’ve made mistakes. I’ve passed out drunk in frat houses. Once, I woke up in a pile of trees after a bender. I’ve done drugs, had meaningless sex, drank until I forgot my name. Like many kids from the Ignatius and Catholic school world, I grew up too fast. Fake IDs, high-end clubs, cocaine, pills, sex, vodka in water bottles at school—we wore chaos like a designer brand.

We were young. We were “privileged.” We were lost.

And yet, I made it out—scarred, scared at times, defeated, trampled, and broken. I was told I had a rowboat while names like Conforti and Nudo had ships. I laugh now, because they were right—they did have the ships. But even the Titanic sank.

And it wasn’t the grand vessel that saved anyone—it was the rowboats. Small, battered, half-submerged. They didn’t reach the shore on their own, but they stayed afloat long enough to be rescued. They carried the ones who refused to drown.

I made it out in my own broken, water-filled rowboat—clutching hope at the eleventh hour. And I sit here now, not with shame, but with pride. Because survival wasn’t handed to me in comfort or legacy. I survived because I refused to go under.

Some of the same men who tried to humiliate me—like Anthony Conforti—still haunt the dark corners of the Viagra Triangle, a pocket of Gold Coast bars and hotels where old money goes to feel young again. Some nights, he’s still there—with a pocket full of hundreds and a handful of cocaine, trying to forget the pain for just one more night.

That’s not power. That’s prison.

Meanwhile, John Donovan, son of Thomas, now advises Sheriff Tom Dart and has moved into—you guessed it—cannabis. It’s the new frontier for the old Machine. Everyone has a cousin or a friend with a license. The same names. The same game. And for the record, Thomas Donovan has never been publicly linked to criminal wrongdoing, and I do not accuse him of it. But I will share what was told me once at a dinner, as I remember it: a Wintrust executive, casually but clearly, once called him and his wife “criminals” who “should be in jail.” I never asked why. But that banker handles a lot of money and speaks with the confidence of someone who knows where the bodies are buried.It’s worth noting that Toni Preckwinkle—the Cook County Board President—once returned a campaign donation from Thomas Donovan PUBLIC RECORD. Quietly. No press release. Just... gone.

So, when I say the Catholic school system formed a bloodline of power, I don’t mean that metaphorically.

At St. Ignatius—one of the Vatican’s crown jewels in Chicago—I walked the same halls as the scions of influential families. In the trophy cases and honor boards, names like Daley, Madigan, Burke, Hynes, and Stroger appeared like scripture. This wasn’t legacy—it was lineage. John P. Daley, future Cook County Commissioner, and William Daley, future U.S. Commerce Secretary, both graduated from there in the 1960s. Todd Stroger, class of ’81, would become President of the County Board. The Jesuits taught us to be “men and women for others.” But many graduates became men for each other—a fraternity of clout.

And behind them, in the quiet shadow: Rome.

Behind the ivy-covered walls and Latin mottos, we witnessed favoritism up close. In my years at Saint Ignatius, the unspoken rule was that who your parents were mattered as much as your grades. A quiet word from a well-connected mom could get disciplinary “incidents” swept aside. A donation to the right Catholic charity could secure a troubled kid’s admission or transfer. We pretended our school was a meritocracy under God, but we all knew which students were untouchable. These were the sons and daughters of Chicago’s Vatican-linked families – those who had priests over for dinner, who sat on boards of Catholic nonprofits, who counted bishops as family friends. They would one day intermarry, consolidate wealth, and dole out favors to each other’s businesses. In Chicago, the altar is just an antechamber to City Hall.

I recall an Ignatius classmate – I’ll call him “M.” – who casually used racial slurs in the cafeteria, knowing the administration wouldn’t punish a legacy kid. When a brave group of minority students staged a silent protest in 2016 to “reject the deeply embedded culture of oppression” at Ignatius, the school’s initial reaction was defensive ​chicago.suntimes.com​. Only after public pressure did leaders vow to address the racism. But the truth is, those elite Catholic institutions long cultivated a culture of silence. If you were harassed or abused by someone with clout, you stayed quiet. If you wanted to remain in the charmed circle, you laughed off the casual racism and corruption as “just how things are.” I did – until I couldn’t anymore.

Nonprofits and Patronage with a Papal Blessing

Outside the schools, a web of Catholic-affiliated nonprofits groomed generation after generation for power – often under benevolent guises. After School Matters, the crown jewel youth program founded by Maggie Daley (the late First Lady of Chicago), was one such endeavor. Maggie, devout and educated by nuns herself, poured her energy into this charity “to provide activities for Chicago Public School students”​chicagocatholic.com. It was lauded as an altruistic partnership between City Hall and the community. But behind the scenes, ASM became a fertile recruiting ground and PR machine for the elite. Daley allies and archdiocesan figures populated its board, including both generations of Marchese’s, me, and others. Cardinal Francis George praised Maggie’s work, and the Chicago Catholic publication noted how she “touched the lives of many” through her charitable works ​chicagocatholic.com. Of course, it did – charity is the soft glove that hides the iron fist of influence. Through programs like these, the Daley network identified loyal talent, bestowed small favors (internships, recommendations), and inculcated gratitude in a new generation. Some of those kids would rise, pay homage to the Machine, and keep the cycle going.

Another pillar of this Vatican-sponsored influence was Old St. Patrick’s Church itself. Once a dying parish in a fading patch of town, it was miraculously reborn under Father Jack Wall—my former pastor and a charismatic operator.

I still remember the first time I saw Father Jack Wall. My nana—a devoted Irish Catholic and lifelong social worker at Catholic Charities—leaned over during Mass one morning and whispered how handsome he was “for a priest.” She pointed out that, in her mind, they both had piercing blue eyes. She wasn’t wrong. Back then, it was rumored that Father Wall rode a Harley. He had that quiet rebel’s aesthetic, draped in a collar. That contradiction made him captivating to everyone around him.

My nana practically raised me while my mom was still figuring out life. By the time she did, she married a Chicago police officer who used to tell her and me wild horror stories from his beat, which included calls to Cabrini Green from time to time. It was such a typical Chicago thing for my mom to do—settle down quietly on the South Side, play golf, convert to Buddhism, and move on from brief stints as a nurse and in IT before her passing. Her life was a quiet one, marked by survival.

My grandmother’s was not. She worked downtown at Catholic Charities, then headquartered at 651 W. Lake Street. After her divorce, she told me stories—frank ones. Apparently, her husband, Dr. Tribbett, a prominent Yale-educated dentist at the time, left her for a man he’d fallen in love with. Back then, that wasn’t accepted the way it might be now. I wish I could say my nana had compassion. But not so much. I vividly remember her telling me she used to place pin needles point-up on his side of the bed—her quiet form of vengeance for the nights he came home late after "hanging with the guys." As a child, I used to wonder how much patience that must’ve taken to line up each little needle in the dark. Some of her friends told me that during the divorce, at a party once, she climbed up on a table to take down the crystal chandelier, swearing it was hers.

The women in my family? We fight. Some have been arrested for assault, including myself. But one might argue—we were provoked. And I suppose in a Pill Hill house full of betrayal and bone china, the chandelier was worth the climb.

That same Catholic Charities 651 W. Lake building became part of my daily routine. Before school, I’d sit under my nana’s desk playing with paperclips and pens while she prepped for casework. I remember those long rows of grey cubicles like it was yesterday—a cold, fluorescent-lit labyrinth. I’d run through them looking for fun, for warmth, for a little bit of magic, not realizing I was racing through the quiet machinery of a powerful, cloaked system.

The loop was always the same: Catholic Charities → Old St. Pat’s → Catholic Charities again, maybe a pit stop at FraskTrack for French fries if I behaved, then home. That cycle trained me in more ways than I realized. I was too young then to understand that I was being conditioned—groomed to live inside a system that rewards loyalty, discourages questions, and masks spiritual control as community care.

It was the start of what I now recognize as a self-built prison, constructed through routine, tradition, and false belonging. A place where I was meant to find safety—but instead found surveillance, silence, and the earliest seeds of shame.

Over 24 years, Father Wall grew Old St. Pat’s from 4 households to 4,000, transforming it into “one of the most vibrant faith communities in Chicago”​catholicextension.org. But Wall’s ambitions didn’t stop at the altar. In 2007, the Holy See tapped him directly, appointing him President of the Catholic Extension Society, a papal society funding churches nationwide ​catholicextension.org​. The Vatican doesn’t hand out such roles randomly; Wall had proven he could marshal wealthy Chicago Catholics – the same power players who jetted off to Rome for papal honors – to bankroll the Church’s missions. Under the charity banner, Father Wall brokered partnerships between monied families and pet causes. The powerful found salvation (and tax write-offs), the Church found patrons, and a discreet quid pro quo endured. I remember it firsthand. I was there as a child—under the tables. Invisible. I watched as they traded reverence for influence. I have memories of gala dinners being set up at the Old St. Pat’s rectory, where CEOs and judges sipped wine beneath relics of the saints. Deals were made alongside prayers. A construction contract for a loyal parishioner here, a city appointment for a Knights of Columbus Grand Knight there. I absorbed the lesson that piety and patronage go hand in hand in Chicago.

And then there were moments more personal. I remember my uncle—well, technically my mother’s cousin, but always introduced as “Uncle”—Alvin Boutte, the son of Alvin Boutte Sr., founder of Independence Bank, Chicago’s first Black-owned bank. A legacy child of the system, he would speak casually of how the priests and nonprofit board members he worked with would get “drunk into oblivion” before their meetings. There was no shame in it—just ritual—another night in the sacredpolitical circuit of Chicago.

Uncle Alvin always tried to look out for me in his way. A good soldier of the Order. Loyal. Dutiful. But I knew even then that his path could never be mine. The world he followed demanded silence, compromise, and performance. I couldn’t follow it and expect to protect myself—or my children. I owed myself and them better.

He, too, has had his share of troubles. But when I see him now, I don’t see a villain—I see another victim of the trauma cycle. Another man caught in the loop. Another one who never found the exit.

Even ostensibly secular charities often had the Church’s fingerprints. Take After School Matters again – while not officially a Catholic organization, it thrived in the slipstream of the Daley administration’s Catholic connections. The program’s meteoric expansion relied on city grants and partnerships with schools like St. Ignatius and De La Salle (Mayor Daley’s alma mater). Maggie Daley herself was educated by the Sisters of Notre Dame; she brought that network of nuns and donors into her youth programs. Parish basements hosted dance classes; convents supplied volunteers. The Holy See’s shadow was there, financing summer jobs and art projects while quietly reinforcing the Daley brand in every neighborhood. The Vatican’s support was indirect but palpable – a bishop at a ribbon-cutting, a homily praising “the dignity of work” for teens. It was good press for the Church and the city’s rulers, even as both institutions hid their rot behind smiling children on stage.

Schools of Power and Silence

The Catholic school system in Chicago didn’t just educate the elite – it engineered them. For over a century, schools like St. Ignatius, Loyola Academy, Notre Dame College Prep, and others have funneled well-connected graduates into the highest echelons of power. The Daleys, the Burkes, the Madigans, the Donovans, the Cullertons – all these political families sent their progeny to Catholic academies. Why? Because it created a pipeline of influence. Classmates today, co-conspirators tomorrow. We were taught to see each other as family – a family that would quietly bury any secrets to protect its own. One Ignatius president (a Jesuit whose tenure spanned decades) liked to toast at reunions: “Once a Wolfpacker, always a Wolfpacker,” invoking the school mascot. Only later did I understand how ominous that was. It meant that no matter what happened – a DUI, an accusation, a scandal – the pack would circle and defend. A former student recalled an event on a message chain, “…On May 5, 1993, three male students dragged a female student into the boy’s locker room. When they finished whatever, they did, they left an imprint of her face in the concrete...”  If a favored student was caught dealing drugs, he’d be quietly withdrawn, not arrested. If a beloved teacher was accused of “overstepping” with a girl, she’d be urged to forgive and forget, for the good of the community. If a teacher got caught drinking on the job and yelling or throwing textbooks at students, God’s will conveniently aligned with protecting the school’s reputation.

But some truths were too horrifying to fully suppress. Whispers of child abuse by clergy occasionally pierced our bubble. A certain priest abruptly “went on leave” one semester; only years later did I learn he had been molesting boys in the locker room. The archdiocese’s response was predictable: shuffle him off, paper over the past. Files later showed that Chicago Church officials had knowingly reassigned abusive priests for decades, hiding their crimes from parishioners ​cbsnews.com​cbsnews.com. In one case, a teenage girl reported abuse in 1970,and Cardinal Cody himself wrote that the “whole matter has been forgotten” to avoid scandal ​cbsnews.com. Another memo to Cardinal Bernardin in 1989 fretted that a key parishioner had learned of a priest’s history with “young boys,” prompting the priest’s transfer yet again ​cbsnews.com. We, the children, were the sacrifices on this altar of silence. And many of us didn’t realize until adulthood what had been taken from us—or nearly taken. Some wounds we carried without knowing their names. I count myself among the lucky. My scars are psychological, emotional, mental—and yes, physical—but at least some parts of my body were left intact. Others weren’t so fortunate. Some didn’t just lose safety or innocence—they lost their voices, their futures, their lives. And the worst part? The ones who took the most still sit in pews and boardrooms, cloaked in respectability, as if nothing ever happened.

Inside the rarefied world of Catholic schools, racial violence was less overt but ever-present. As a lone Black girl at a mostly white, wealthy academy, I felt it in the slight snubs, the missing invitations, the way my achievements were often attributed to “diversity quotas.” The very same institutions claiming to instill Christian values were perpetuating class and race divides. It was an open secret that St. Ignatius’ scholarship students – often students of color from humbler backgrounds – were treated as charity cases rather than equals. Some alumni, now city officials, still carry that entitlement. They believe Chicago is theirs to rule, ordained by birth and blessed by the Holy Mother Church. And to a frightening extent, they’re right.

The Vatican’s Shadow Empire

Through its schools, churches, and nonprofits, the Holy See built a shadow empire in Chicago – one that bolstered the city’s political dynasty at every turn. Consider the tangle of relationships: Daley cronies sit on Catholic school boards; those schools produce grads who become aldermen, judges, and commissioners; those officials then steer city contracts to businesses run by fellow alumni or parish members. It’s a closed loop, sanctified by religion. Marriage is another currency of power. The Machine’s families often intermarried at society weddings blessed by bishops. Each union tied together money, influence, and Church approval. The Marasso clan (by marriage linked to the old 1st Ward Roti machine) is entwined with city contracts – a son-in-law of a Chicago alderman famously leapt from a lowly job to a high-paid O’Hare manager overnight in the 1980s ​ilga.gov​. The Moffatts and others likewise leveraged faith-based connections to secure lucrative deals in real estate and construction. They meet not in smoke-filled back rooms, but at the White Mass, Mass on Ogden, and the Knights of Columbus hall. In Springfield and Chicago today, many holding the levers of power – in the cannabis industry, law firms, tech startups, and of course, government – are benefactors of this system. They are the children (and now grandchildren) of the Daley-era Catholic Clout. They might have new last names and titles, but their privilege was baptized in the same font.

To maintain control, these families and their Vatican enablers practice gatekeeping as an art. They cloak exclusion in righteousness. A young reformer might run for office, but if they didn’t come through the “right” schools or parishes, the Catholic network would subtly undermine them – endorsements withheld, whispers of being “not a good fit.” Meanwhile, when they do anoint a person of color or an immigrant as a candidate, it’s often someone like Hoan Huynh. Huynh, a Yale-educatedfresh face who made history as the first Vietnamese American in the Illinois House, presented as a progressive trailblazer. Yet behind him stand the same old hands: Daley operatives, Boutte,and Tribbett family allies quietly pulling strings. I witnessed it: a birthday party fundraiser for Huynh that felt like a Daley family reunion, Machine stalwarts slapping his back. Even Alexi said a few “inspiring words” that sounded more like Obama-type practice for the future.

Alexi Giannoulias, educated at the Latin School of Chicago and baptized by the city’s elite, has long been groomed by the Machine. His tenure as Illinois State Treasurer was tainted by the collapse of his family’s Broadway Bank, seized by federal regulators in 2010 after it was revealed the institution made risky loans—including to convicted felons and organized crime figures politico.com. But in Chicago, scandals don’t end careers—they just go dormant until the public forgets.

And forget, they did—long enough for Giannoulias to be maneuvered into the office of Secretary of State in 2022, not as redemption, but as a calculated step toward a higher throne—perhaps mayor or beyond. This wasn’t a comeback. It was a setup.

Adding to the intrigue is his personal tie to the Daley dynasty. Years ago, Alexi was engaged to Tara Flocco, a Saint Ignatius graduate from a modest background whose family married her up for higher social standing. Tara would later marry Patrick Daley, son of former Mayor Richard M. Daley—a union engineered more for optics than affection. That marriage has since ended in divorce. chicago.suntimes.com

These connections aren't coincidence—they’re currency. In this city, the Machine swaps players like cards, reshuffles names and bloodlines, and runs the same candidates through a new wash cycle until they’re deemed “clean” enough to push again. Giannoulias is just the latest example of this generational rebranding. And it’s all part of the long game—to restore the Machine to full operational power.

His victory was their victory – a way to maintain influence in a diverse district by installing a friendly figurehead. This is how racial, and class gatekeeping adapts: if you can’t bar the door, you let in someone who will carry your water. And so, the Holy See’s chosen – the polished, compliant alumni of its grooming system – continue to hold the keys to the kingdom, even as the city’s demographics change. The faces get browner, the rhetoric more inclusive, but the patronage and clout remain as exclusive as ever.

Past Sins Cast Long Shadows

The corruption blessed in backrooms and sacristies long ago still haunts us. Chicago’s present is shackled to its past by chains of deceit and cover-ups. We see it in scandal after scandal, each a variation on an old theme. For instance, the infamous parking meter deal of 2008 mentioned in part 1 sold our city’s revenue to foreign investors in a cloaked, rushed arrangement that reeked of backroom collusion ​washingtonexaminer.com​. (Some even dub it the “Chinese parking meter deal,” mistakenly or not, to underscore how our public assets were bartered away to shadowy global funds.) Mayor Daley, ever the dutiful Catholic son, pushed that 75-year deal through with lightning speed, perhaps counting on a forgiving press and a distracted public ​washingtonexaminer.com​. The result? Chicagoans left paying sky-high rates to enrich a private consortium that had already recouped its entire $1.16 billion investment within a few years ​washingtonexaminer.com​. That consortium included entities like Morgan Stanley and foreign sovereign wealth funds – deals blessed in the marble halls of banks rather than cathedrals butblessed all the same. The moral failure was akin to the Church’s own: secrecy, lack of accountability, and betrayal of the people’s trust.

History provides even starker parallels. In the 1980s, the Franklin cover-up scandal in Omaha exposed a grisly intersection of power, abuse, and conspiracy. It revolved around allegations that prominent politicians and businessmen were part of a child sex trafficking ring. Officially, grand juries called it a “carefully crafted hoax.”​theamericanconservative.com Yet investigators and journalists later uncovered frightening unanswered questions – evidence destroyed, witnesses discredited or turning up dead, and a deep reluctance by authorities to dig further ​theamericanconservative.com​. The machinery of suppression was in full force, much like it has been in Chicago’s Catholic institutions. I mention Franklin because the pattern is painfully familiar: powerful figures preying on the vulnerable and a vast system of enablers ensuring no one is ever held to account. The Archdiocese of Chicago operated on the same principle for decades. Files released in 2014 showed “disturbing details of high-level efforts by the Catholic Church in Chicago to stonewall abuse victims” and protect abusive priests ​cbsnews.com​. As one outraged victim put it in a letter to Cardinal George, “Where was the church for the victims? … We were children, for God’s sake.”​cbsnews.com​The Franklin case may have been hundreds of miles away and centered on a different set of elites (and a different church, in part), but it lives in the same universe of systemic evil cloaked in respectability. Chicago’s corruption dynasty has always had its hands dirty with similar sins – ones it will go to any length to hide.

Look no further than today’s headlines for proof that the Machine’s playbook endures. In the burgeoning Illinois cannabis industry – a new gold rush dominated by the well-connected – we have our own saga of deceit. Courageous individuals like Joseph Phelan and Juan Finch Jr. learned this the hard way. They blew open the doors on nuEra, a cannabis company that branded itself as family-owned and upstanding. What they alleged was a litany of fraud: nuEra’s executives, including a member of the Daley clan by marriage, rigged the game to maintain their monopoly. According to Finch’s lawsuit, nuEra used him as a pawn – a token minority – to challenge Illinois’ social equity licensing, effectively delaying opportunities for other minority entrepreneurs ​issuewire.com​.It’s the same old strategy of co-opting and undermining diversity initiatives, wearing a new mask. Phelan and Finch also claim regulators turned a blind eye to nuEra’s misconduct because the company “owns the state and politicians” – boasting that they had so much money and clout that no one would dare touch them​ linkedin.com​. When they didn’t back down, they say, the cover-up kicked in: evidence hack attempts, state agencies refusing to investigate “felony-level crimes,” and the legal system itself slow-walking justice ​linkedin.com​ I’ve seen some of the evidence with my own eyes – bank transfers, internal emails – and it’s sickeningly reminiscent of how the archdiocesehandled abuse: deny, delay, dismiss.

And then there’s METRC, the tracking software meant to ensure every gram of legal cannabis is accounted for. Marcus Estes’ new lawsuit in California echoes many of the same allegations raised by Joseph Phelan in Illinois—namely, that METRC’s system was intentionally vulnerable, enabling insider manipulation and regulatory blindness. Yet despite these red flags, Illinois fast-tracked METRC’s approval as the state’s official cannabis tracking vendor in February 2025, raising serious questions about political influence and backdoor deals.It’s the contemporary equivalent of a church ledger – supposed to guarantee honesty. Yet reports from other states suggest METRC can be gamed. Estes’ bombshell whistleblower lawsuit on the West Coast alleges METRC and regulators conspired to ignore huge discrepancies, allowing licensed firms to divert product to the black market ​ganjapreneur.com​. In other words, the watchdog chose to look away as the wolves feasted. Illinois only adopted METRC recently, and already questions swirl about irregularities in supply numbers and “mistakes” that always seem to benefit the big players. How convenient. It appears that even our high-tech safeguards are only as good as the integrity of those running them – and integrity is one thing the corruption dynasty consistently lacks. If METRC’s system was intentionally left leaky, that’s just the new digital face of the age-old grift.

From Darkness to Light (a Memoir-Opinion)

I share these stories not as detached reportage but as someone who lived this reality from crib to college and beyond. This is my Chicago – a city where all roads of power truly lead to Rome, where the hand of the Holy See has guided, shielded, and at times strangled the body politic. The Vatican’s covert role in Chicago’s corruption dynasty is the skeleton key that unlocks so many of our city’s secrets. It’s there in the nuns who groomed children for obedience, the priests who whispered absolution to mobsters, the cardinals who traded favors with mayors. It’s there in how a select group of Catholic schools and charities became conveyor belts to influence, spitting out generation after generation of leaders convinced of their divine right to rule – and to exploit.

But if this sounds bleak, know that exposing it is an act of faith for me – faith that truth can purify. I am Brittini Flatley, The Rose that grew from the Machine’s concrete, the insider who won’t sit still and be quiet on the outside.

I speak in a voice my elders tried to silence with hymns and threats, a voice now fully my own. And I’ll keep speaking because I owe it to the children hurt by all this: the abused, the marginalized, the ones told they didn’t belong. In telling my story, I tell theirs. In calling out names, I honor those who had theirs taken away or dragged through the mud.

In Part 3 of this series, we will venture even deeper into the heart of darkness. We’ll confront the topics that make even the most jaded Chicagoans flinch: child abuse in the halls of power, psychological grooming in the guise of mentorship, and the systemic silence enforced by fear.

And we will name names—because many of those complicit didn’t just look the other way; they helped build the institutions that protected abusers. Some of the very families we’ve already discussed—the Daleys, their inner circle, their business allies—sat on the boards, funded the schools, and signed off on the silence.

We’ll connect the dots from the Catholic school playground bully who became a predatory CEO, to the hush-hush “therapy retreats” in Wisconsin and Missouri where wayward priests were quietly parked, to the still-unsolved mysteries that echo Franklin, Epstein, and yes—Chicago’s own whispers that never made the news.

It won’t be easy reading. But it will be the truth. And as I’ve learned, the truth, no matter how painful, will set Chicago free.

Because when priests are protected by politicians, and the politicians are protected by old money, and the old money sends their kids to the same Jesuit schools that taught us to stay quiet—you realize this wasn’t accidental. It was designed.

We will explore how boys and girls like Michael and Christine Daley—twins of John Daley, who couldn’t even get into St. Ignatius—still found themselves ushered through elite networks, while Black and brown children were held to impossible standards and punished for the smallest offenses.

We will revisit old corridors where kids were silenced and exploited. And we will follow those corridors all the way up the ladder—into city contracts, real estate syndicates, and political appointments that served as payoffs for loyalty and hush.

The road ahead is fraught. But it leads toward light.

Stay tuned. Stay strong.

The era of silence is over.

Sources:

• Chicago Archdiocese cover-up: documents show Cardinal John Cody assured an accused priest the abuse allegation was “forgotten”​cbsnews.com; memos to Cardinal Bernardin reveal abusive priests were repeatedly moved to hide their misconduct ​cbsnews.com.

• Latin School elitism and racial culture: Charles A. TribbettIII, a board member at the Latin School of Chicago and father to alumni, distinguished the institution as part of a more exclusive class of private schools. Latin has faced criticism for fostering a racially exclusionary culture, with students and alumni publicly speaking out about systemic bias injusticewatch.org. Tuition at schools like Saint Ignatius College Prep often exceeds the median annual salary of many working families injusticewatch.org.

• Maggie Daley’s After School Matters: founded by Chicago’s former First Lady to help CPS students ​chicagocatholic.com, illustrating elite Catholic influence in youth programs ​chicagocatholic.com.

• Father Jack Wall & Vatican: longtime Old St. Pat’s pastor Jack Wall grew the parish from 4 to 4,000 families and was appointed by the Pope in 2007 to lead Catholic Extension ​catholicextension.org​ – a direct Holy See link.

• St. Ignatius College Prep alumni in power: e.g. John P. Daley ’65 (Cook Co. Commissioner) and William Daley ’66 (U.S. Commerce Sec.) ​ignatius.org; Michael Madigan ’60 (IL House Speaker) ​lib.niu.edu; Todd Stroger ’81 (Cook Co. Board President) ​ignatius.org – showcasing the school’s role in forming Chicago’s governing class.

• Racism at St. Ignatius: minority students protested a “culture of oppression” in 2016​chicago.suntimes.com; the administration belatedly addressed racism amid public pressure ​chicago.suntimes.com.

• Broadway Bank collapse: Giannoulias' family bank, Broadway Bank, was seized by federal regulators in 2010 after failing to raise sufficient capital. The bank's failure cost the FDIC's insurance fund approximately $394 million, with losses attributed to risky loans, including those to convicted felons. ​nbcchicago.com

• Political maneuvering: Despite the bank's collapse, Giannoulias received campaign contributions from former Broadway Bank officials during his 2022 run for Illinois Secretary of State, raising concerns about the recycling of political figures by the Chicago Machine. ​Chicago Sun-Times

• Parking meter deal fiasco: pushed by Mayor Richard M. Daley in 2008, leasing Chicago’s meters for 75 years; by 2023 investors had recouped their full $1.16B investment plus $500M profit ​washingtonexaminer.com​, while taxpayers got locked into a bad deal ​washingtonexaminer.com.

• Franklin scandal (1988): Alleged child sex ring among Omaha elites officially deemed a hoax, but it “left many questions unanswered”​theamericanconservative.com; whistleblower Nick Bryant likened Franklin’s cover-up to Epstein’s, underscoring persistent elite impunity​theamericanconservative.com.

• NuEra cannabis scandal: Whistleblower Juan Finch Jr. alleges nuEra (with Daley family ties) used him to undermine Illinois’ equity program ​issuewire.com, boasting they “own” politicians ​linkedin.com; state regulators refused to act on evidence of crimes ​linkedin.com.

• Maple & Ash controversy: The luxury steakhouse chain frequented by Chicago’s elite—including figures like Conforti—has come under fire for internal power struggles, lavish spending, and a federal investigation into alleged PPP loan fraud chicago.eater.com; the Gold Coast location, once a symbol of status, now reflects a familiar tale of money, ego, and implosion chicago.eater.com.

• Maple & Ash investor dispute: The high-grossing restaurant chain—anchored in Chicago, and Scottsdale—has drawn scrutiny for internal power struggles and undisclosed financial arrangements, with powerhouse investors like Rossi and Cosich linked to the brand’s rise wbez.org; a 2024 dispute exposed conflicts over ownership and accounting practices wbez.org.

• Metrc tracking failures: A 2023 lawsuit by a former Metrcexec claims California regulators and Metrc let licensed distributors divert cannabis to the black market by ignoring suspicious data ​ganjapreneur.com, calling into question the integrity of seed-to-sale tracking systems.

• Chicago Cartel cannabis lawsuit: A 2022 federal complaint alleges four marijuana companies in Illinois are part of a “Chicago Cartel” accused of racketeering, corruption, and abusing state cannabis licenses to consolidate power and block competition mjbizdaily.com.​

• Part 1 Reference: Brittini Flatley, “Chicago’s Corruption Dynasty: The Daley Machine’s Destruction and Its Living Legacy,” LinkedIn (Introduction/Part 1 of series)​https://www.fnaround.com/thegarden/part1.

Legal + Personal Disclaimer

This memoir series is a personal narrative based on my direct lived experiences, personal memories, and documented interactions. All opinions expressed are my own and are protected under the First Amendment as personal commentary and constitutionally protected speech.

Where individuals, institutions, or events are referenced, they are either (a) public figures or publicly known entities, (b) part of publicly accessible historical records, or (c) mentioned strictly in the context of my personal experience or direct knowledge at the time.

This series does not allege criminal conduct unless otherwise supported by publicly available documentation, filed legal complaints, or formal testimony. Any perceived connections or conclusions are drawn from my own interpretation and experiences, not intended as definitive statements of fact beyond my personal scope.

Nothing in this publication is presented as a legal accusation, defamation, or threat. It is part of an ongoing, protected, and constitutionally lawful exploration of historical and systemic patterns as I have experienced and witnessed them.

If any party mentioned wishes to request a correction or response, they are encouraged to reach out directly. This series aims to uplift truth, protect free speech, and empower others who have experienced similar dynamics.

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© 2025 Brittini Jerale Tribbett and F’nAround Media. All rights reserved.

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Author’s Note:

This series is a protected work of memoir and opinion, based on personal lived experience, investigatory research, and interpretation of public events. Allegations remain allegations unless proven in a court of law. This publication is offered under constitutionally protected freedom of speech, freedom of the press, and journalistic activity as recognized by U.S. and international law.