Austin Berg wanted to talk about structure before we talked about anyone’s name. We sat down in Lincoln Square on a summer afternoon. The problem, in his telling, is the shape of the government itself, more than any one mayor.

Berg has spent a decade on that argument. He runs the Chicago Policy Center, an arm of the free-market Illinois Policy Institute, writes The Last Ward to more than 158,000 subscribers, and co-wrote The New Chicago Way. What he wanted to litigate was the machinery.

“Among the big cities, we have the most vestiges of a strongman, almost caudillo, sort of system,” he said. A weak council, often seated by the mayor. No city charter. No elected finance officer or city attorney. No public vote on debt or taxes. Among big cities, Chicago stands out for having none.

Waiting for Superman

I asked whether the 2027 mayor’s race matters or whether it is a field competing to run a broken machine. Berg has a name for the reflex behind the question.

“The mayor’s race is the lens through which Chicagoans understand city politics more than anything else,” he said. “This is a pathology.” He calls it waiting for Superman. The city looks to one person for salvation because the strong-mayor system trained it to.

The office matters to him. What the city gets wrong, he says, is what it expects the office to do. “It’s a necessary condition to have good leadership,” he told me. “It’s not a sufficient condition to have a growing, thriving city.” The candidates he watches for are the ones who ask a longer question.

“Public office does not create intellectual capital. It consumes intellectual capital.”

Most people who run for mayor arrive without much of it, he said, because the way the city actually works sits below the headlines. His group briefs candidates across the spectrum on their real options. The ones who stand out, in his telling, ask what they can build now that leaves the city stronger on its 200th birthday in 2037, whoever holds the office by then.

The $11 billion

To see the structure work, Berg said, look at last year in Springfield. A pension sweetener added about $11 billion in liabilities to Chicago. The immediate annual cost he put at $30 to $50 million, enough to double the city’s summer jobs program, one of the few Johnson initiatives he credits.

The mechanics are what he returns to. “They just made the promise. They didn’t make the tax,” he said. The state assigned the liability and left the city to find the money. Chicago got no vote, and by his account, learned the full scope only days after the session closed.

The city’s chief financial officer at the time, Jill Jaworski, warned in writing that the change would push the pensions toward insolvency. Berg says he was the first to publish that letter. The mayor did not fight it in public. Berg reads the silence as a symptom of the same structure. A mayor with little standing in Springfield absorbs a bill the city did not get to weigh.

There is another read of the deal. The Tier 2 benefits it raised had drifted below the federal Social Security “safe harbor,” the rule that a public pension must pay at least as much as Social Security would. Falling short risked forcing Chicago to enroll those workers in Social Security or cover the gap through lawsuits, an exposure that the nonpartisan Center for Tax and Budget Accountability estimated at over $800 million a year. Roosevelt University’s Ralph Martire, who directs it, told WTTW the law fixes a real structural flaw, while faulting how it was paid for. Berg’s quarrel is with that second part, the promise without the money.

A release valve

Other cities have an exit from a bill like that. Chicago does not. “Detroit today has a better credit rating than the city of Chicago,” Berg said, and Detroit is a decade past bankruptcy. Chicago is the only city among the fifteen largest that cannot take its debts to a bankruptcy judge.

He calls Chapter 9 a last resort and wants a framework for distressed cities in place before it. An early-warning system on municipal finances. State oversight when a city runs past its means. An emergency manager who can reach a judge only at the very end. Harvey, the south-suburban city that cannot collect enough property tax to cover its debts, is his warning case.

The authority matters even when unused, he argues, because it rewrites the conversation with creditors and unions. “We can either negotiate in good faith right now,” he said, describing the leverage, “or this can go to a judge, and then it’s out of our hands.” He points to the parking meter deal as the price of having no such card to play.

The case against the tax

Berg’s tax politics start with population. “Our biggest problem as a state is three words,” he said. “People, people, people.” Illinois lost roughly a million residents over the past decade, and by his reading, the highest earners leave fastest, two out for every one in.

That is the frame for his objection to the proposed 3 percent surtax on income above $1 million. He is careful about who he is defending. “I’m not asking people to shed a tear for a pinstripe-suit, Rolex-wearing millionaire,” he said. His worry is the roughly 22,000 pass-through businesses that file at that line, the tradespeople and small operators he credits with most of the state’s new jobs, and the tax base that leaves with them. He points to Massachusetts, the one state to run a comparable surcharge. “The entire pie of the income in Massachusetts shrunk,” he said.

That read is contested, the migration piece most of all. Cornell sociologist Cristobal Young, working with two US Treasury economists, tracked every million-dollar tax return in the country over thirteen years for a study in the American Sociological Review. The rich, they found, change states at 2.4 percent a year, compared with 2.9 percent for everyone else. Tax flight runs only at the margins. The Illinois Economic Policy Institute reached a parallel result in 2026, finding that states with millionaires’ taxes grew about as fast as those without, and that a 3 percent version could raise more than $4 billion a year for schools or property tax relief. Illinois voters backed the idea in a 2024 advisory referendum, roughly 60 percent in favor. GrayStak holds no position.

Where he draws the line

On the state’s investment exclusion lists, Berg draws a line between the money a government spends and the money it owes its retirees."The Illinois Investment Policy Board keeps a set of those lists, built one cause at a time. Companies that boycott Israel. Firms that house migrant children. Businesses tied to Iran and Russia. Every state pension fund has to divest from the names on them and stay clear, and much of that territory already overlaps with federal sanctions. I asked whether a fiduciary duty, applied evenly, cuts against every screen on the list, whatever the cause.

He said it is not an issue he has worked on closely, then split the question. A state can invest by its values, the way a university weighs its endowment, and he recalled the campus fights over how endowments should be run. “You can make values-based decisions on how you want to invest,” he said. “What I don’t like is when people think there’s no trade-offs to that.”

The pension is where he holds the line. "If I'm personally responsible for managing the money of Illinois teachers' pension funds, and I need this money to exist or else someone's not getting their retirement check," he said, "my operating principle would be, you have to maximize the returns. That is the single thing you should be focused on." Political screens, whatever the cause, are "a Pandora's box" that reduces returns by necessity. Values-based choices he keeps to the operating budget, the programs a government chooses to fund.

He pointed to a case. Former Chicago City Treasurer Melissa Conyears-Ervin moved to halt the city's purchases of US Treasuries, citing the city's ability to earn the same returns elsewhere. Berg's answer was that Treasuries are the safest and most liquid asset there is, and a global benchmark. "If you're going to counter the benchmark, you need a good benchmark to counter." Pressed on what replaces it, he said no answer comes back. "China doesn't exclude the US Treasury."

Applied across the board, his answer holds for every list, regardless of the target. A political screen on pension money is a political screen, and by his principle, it works against the funds it is meant to protect.

Show your work

Berg likes the ideas grouped under “abundance,” which he reads as a catch-all for sustainable growth, and holds the label itself at some distance. His caution is with how the word gets used in a campaign. Every challenger will promise to grow the city, he said, because growth lets them avoid having to name a tax hike or a cut. “People should ask for specifics,” he said. “What do you mean by growth? What levers will you actually pull?”

His own answers start with certainty. A business plans around what it can see, and Chicago gives it little to see. “Imagine plopping down a hundred-million-dollar investment on the city of Chicago when you have no idea what it looks like ten years from now,” he said. Budget and tax certainty that lets an investor project a decade out is his first lever. Housing supply is the second. He credits the current administration with some progress on building, says it is not enough, and puts a yes-in-my-backyard stance in the column of things that would help.

Subtraction

The waiting-for-Superman reflex, Berg said, has a twin in public safety. Every flashpoint produces a call for a new office. “The political muscle, similar to this waiting-for-Superman muscle, is that we need to create another new body,” he said. Chicago already runs around eight with some oversight of policing.

He faults the city for looking inward. On the teen “takeovers” that have flared downtown for more than a year, he points to Washington, where the mayor and council passed targeted curfew zones with advance notice and services attached. “They tried it out last year,” he said. “Zero teen trends happened” before the measure lapsed and the problem returned.

His fix is consolidation. He cites two recent Matrix consulting reports, which he calls the largest review of Chicago policing since the study that produced the consent decree after Laquan McDonald’s murder, and argues the city cannot act on them while it keeps standing up new agencies. Los Angeles and its police commission are his model. He notes that the CARE mental-health response is “floundering,” in the Tribune’s words, and that the mayor’s office took down its public dashboard. Chicago police data show homicides up about 8 percent from a year earlier, a real uptick that sits on top of 2025, the city’s lowest homicide year in six decades.

What comes next

Berg wants Chicagoans to lift their heads toward other cities for solutions and to press the 2027 field on what they will leave behind. He and I plan to talk again in the fall, closer to February. His test for the candidates comes down to one question.

“What things can I do as mayor today to structurally strengthen the city, so that it’s stronger no matter who is the mayor?”

Christopher Sweat is an analyst working across finance, technology, and politics and the co-founder and CEO of GrayStak, a media and political risk company covering social and political dynamics and institutional politics at the state, local, and federal levels. He created GrayStak’s Domestic Political Volatility Index (DPVI), which measures political escalation ahead of media consensus. Austin Berg is executive director of the Chicago Policy Center. Quotes are lightly condensed from the recorded conversation for clarity. The full video interview is above. GrayStak holds no position.

We met Vasquez on his own turf, a North Side space he is quick to say is not a taxpayer-funded ward office. He calls it a community hub, a co-op, a place where neighbors come in to work through what they want to get done. He keeps what he jokingly calls movement merch on hand: t-shirts, hats, and the small Chicago Star butterfly pins his team made during last fall’s surge in immigration enforcement. “The public needs to be informed in order to know how to hold government accountable,” he says. The distinction matters to him, and it frames how he describes almost everything else. Power, in his telling, is something you build with other people.

From the cypher to the council

Vasquez, 46, is the son of Guatemalan immigrants and a former battle rapper who performed under the name Prime. His politics started with hip-hop, long before any party. Listening to NWA, KRS-One, and Public Enemy in the late 1990s, he says, gave language to things he had already lived: poverty, being treated as an outsider, friction with police. “Without thinking about the politics of it, you just know it’s a dope song,” he says. “And next thing you know you’re reciting it, you’re thinking about how it speaks to you and your environment.” When he first heard Bernie Sanders in 2015, the pitch felt familiar. Sanders, he says, “sounded like my rap records.” He knocked doors in Iowa, came back and threw a fundraiser that doubled as a concert, and met an organizer recruiting first-time candidates. In 2019 he unseated Ald. Patrick O’Connor, a 36-year incumbent and a former floor leader for Mayor Rahm Emanuel. He describes his first televised debate in the terms he knew best. It “felt like a battle. Back to back to back bars.”

The only socialist to vote yes

What has defined his six years in office is a willingness to break with the left that produced him. The clearest example is on the record. In late 2020, Vasquez broke with the city’s other socialists to vote for Mayor Lori Lightfoot’s 2021 budget, which carried a $94 million property tax increase and passed narrowly. He was the only Democratic Socialists of America member on the council to support it, and the Chicago DSA chapter censured him, its first such censure. He has not recanted. He says the vote was the price of a deal to stop city worker layoffs during the pandemic, and he frames the episode as the recurring fight on the left between purity and governing. “We all agree on goals. We don’t all agree on how to get there,” he says. A movement built by people who have felt cast out, in his telling, has a habit of casting out its own. “Yo, you’re not left enough, so now you’re not a progressive. And it’s like, we’re not gaining power that way.”

His critics on the left framed it as something else. On the floor of that 2020 debate, Socialist Caucus members rejected the same deal he defended as the responsible vote. “Don’t give me crumbs and tell me it’s cake,” Ald. Jeanette Taylor (20th Ward) said of the budget. “We’re in a global pandemic, and there’s no way in the world that we should be balancing this budget on the backs of taxpayers.” To that wing of the left, Vasquez’s pragmatism reads as capitulation. He calls it the price of keeping people from getting hurt.

Asked directly whether he still considers himself a socialist, he does not hedge.

“Government is socialist. You’ve made a social agreement that you think you can do better by pulling your resources together to solve for more people.”

He adds a qualifier, calling himself a coalitionist, and draws a distinction between two kinds of people who share the label. One comes to it through hardship, and he cites Fred Hampton, Martin Luther King, and Harold Washington. The other, he says, is the person whose “mom and dad paid for college and I read Marx.” People who have lived precarity, he argues, learn to compromise because survival requires it. It is a framing that favors his own position, and he makes no apology for it. He sums up his method in the language of an umpire: he calls “balls and strikes,” he says, no matter “who’s on the fifth floor” at City Hall.

At odds with an allied mayor

That posture has put him at odds with Brandon Johnson, the closest thing the Chicago left has to one of its own in the mayor’s office. Vasquez voted against the mayor’s 2026 budget. He says he supports taxing corporations and still calls the mayor’s signature corporate head tax a marketing ploy. The measure, a $33-per-employee monthly tax on companies with at least 500 workers, would have raised about $82 million. His objection, he says, is precision. A broad tax also falls on immigrant- and Black-owned businesses trying to scale, and the city would do better to target industries that have thrived while others have struggled.

“Am I really doing something, or am I saying that we’re doing the corporate head tax, so that people out here movement-wise go, well, clearly that’s progressive?”

Johnson made the opposite case in his own words. Unveiling the budget, the mayor said he would “challenge the ultra-rich,” asking large corporations and the wealthy to carry more so working families would not face higher property, grocery, or garbage taxes. When the council stripped the tax out, he called the result “morally bankrupt,” arguing there was a way to balance the budget without going after working and poor people. His finance team projected the council plan would leave a $163 million hole to be filled mid-year. Johnson ultimately neither signed nor vetoed the $16.6 billion budget, allowing it to take effect.

On the left, losing the head tax read as a gift to the wealthy. Ald. Byron Sigcho-Lopez (25th Ward), a fellow socialist who championed it, called the budget that passed without it “the billionaire budget” and said it was unacceptable to put the burden on the poorest people in the city. The opposition reached beyond the left. Gov. JB Pritzker, a fellow Democrat, also opposed the head tax, calling it a “job killer.” Vasquez lands in neither camp. He says he would tax corporations, just not this one.

On policing, Vasquez makes a budget argument. He says the department should be audited like any other, noting that it takes up roughly half of the corporate fund’s departmental spending, the discretionary pool the city actually controls. The department’s 2026 budget runs about $2.1 billion, and its overtime line alone grew by roughly $101 million. “You talk to the cops, they don’t feel it, they don’t see that money,” he says. “So my premise is, something’s inefficient here. We’ve got to audit this thing.” Johnson, like most politicians, is unwilling to say that publicly, he argues, so the number keeps climbing.

He frames the larger development as a shift in how Chicago governs. By moving the budget cycle up about six weeks, the council was able to draft and pass a spending plan over a mayor’s objection for the first time in the city’s history. Vasquez voted against that plan too, calling both it and the mayor’s version inadequate, yet he counts the council’s new independence as a gain. “The fact that the council is becoming more independent, I think is a good thing for government, because you have a counterbalance.”

The ordinance that was never tested

Immigration is the fight that has consumed his chairmanship of the City Council’s Committee on Immigrant and Refugee Rights, and here the lines with Johnson are less clean. Chicago’s Welcoming City Ordinance, which says city employees will not help enforce federal immigration law, began as a 1985 executive order under Mayor Harold Washington, became law in 2006, and was expanded in 2012. Vasquez says it had never been seriously tested until the past year. After a mass detention incident in June 2025 and a hearing his committee held that July, it became clear that no rule explicitly empowered the Civilian Office of Police Accountability to investigate whether Chicago officers had violated it. His own attempt to fix that was blocked by colleagues. A similar measure led by Ald. Jessie Fuentes (26th Ward) passed in March 2026, and on this one Johnson was a supporter.

Then the issue reached his own staff. His chief of staff, Catherine “Cat” Sharp, was one of the “Broadview Six,” a group of protesters indicted by a federal grand jury in October 2025 over a September protest outside the suburban ICE facility. Prosecutors alleged the group surrounded a federal agent’s vehicle, banged on it, and damaged it. Vasquez characterizes the prosecution as an attempt to frighten people out of dissent. The case then collapsed. Charges against Sharp were dropped in March 2026, and the remaining charges were dismissed with prejudice in May after the U.S. attorney acknowledged the case was tainted and a federal judge said she was shocked by redactions prosecutors had made to grand jury transcripts. Vasquez goes further than the court record, saying the prosecutor “tampered with the grand jury,” and says he wants hearings to put that official under oath. That word is his. What the record establishes is that there was documented prosecutorial misconduct serious enough to end the case.

Legislating at teenagers

The same instinct shaped his opposition to a proposed snap curfew aimed at large gatherings of teenagers. He grounds it in his own adolescence, getting cleared out of Navy Pier by police for gathering to rap while, as he puts it, “the white kids are chilling.” He was arrested twice before he turned 18, once while sitting near friends who were smoking, and says officers ignored him to arrest the three Black kids beside him, then listed him as gang-affiliated anyway. He never got a record. “That changes the trajectory of your whole life,” he says. He does not dismiss the underlying problem. Large groups gather, he acknowledges, and a few make it dangerous for everyone. His complaint is that the city legislates at teenagers without consulting them.

“It’s a whole bunch of old people out here talking about what the teens are doing, and there’s not enough talking to them.”

What he leaves open

He closes on a warning aimed past his own ward, at the mayoral cycles ahead. Chicago tends to pick whoever it thinks can win, he says, with little regard for who can govern a city this large amid a budget gap the city pegged near $1.15 billion. “We like to slug it out.” He wants the next race to be a test of who can do the job.

It is a notable position from a former battle rapper, a politician who built a career on landing the sharper shot, and it is the tension GrayStak went to his office to examine. Vasquez presents himself as a politician who trusts his own judgment of a fight over any faction’s. The censure, the votes against an allied mayor, and the colleagues he has irritated are the evidence he points to. Whether that record reads as principle or as positioning is a judgment we leave to you. The full conversation is above.

Christopher Sweat is co-founder and CEO of GrayStak, which covers social and political dynamics in real time, as well as institutional politics at the local, state, and federal levels. This piece draws on a sit-down interview with Ald. Andre Vasquez at his 40th Ward campaign office; the full conversation runs on video with this piece. Vasquez’s words are quoted from that interview. Other figures, dates, and officials’ public statements have been checked against the record and linked throughout.

Chris Smalls is sitting across from me in Chicago. For six years, he’s been told he was wrong. For six years, he’s been proven right.

He was right that Amazon was an unsafe place to work in the early weeks of the pandemic. He was right that workers at the Staten Island JFK8 warehouse, a million-square-foot facility with ten- to twelve-hour shifts and a thirty-minute lunch break, could win a union election against the second-largest private employer in the country, even when nearly every major labor organization in America believed they couldn’t. Now, at a warehouse where 5,500 workers still don’t have a contract, he says he is right that Amazon will eventually be forced to the bargaining table. The federal government has ruled in his union’s favor on that point twice. Amazon is in court trying to argue that the federal labor board itself shouldn’t exist.

And on May 4, three weeks before this conversation, Smalls decided he was right that Jeff Bezos, the lead sponsor of the Met Gala, should not be allowed to walk a red carpet thirty minutes from the warehouse without consequence.

“There’s no way I’m going to allow this billionaire to come to New York City and do a fashion red carpet gala thirty minutes away from the warehouse that he refuses to negotiate a contract with,” Smalls says. He jumped a barricade. The NYPD tackled him. He spent twenty-four hours in a Manhattan jail. He is now facing charges for resisting arrest, trespass, and three other counts. They get dismissed if he stays out of trouble for six months. His entire life suggests he has no intention of doing that.

“We put so much fear in Jeff Bezos,” he tells me, “that he didn’t show up on the red carpet.”

The book

In two weeks, on June 1, Crown will publish When the Revolution Comes: A Fight for the Future of the Working Class. The memoir opens with a prologue on what it feels like to walk inside a grocery warehouse, then circles back to his childhood and moves chronologically through to the 2022 union victory at JFK8.

It’s not a manifesto, despite the title. Publishers Weekly called it “plainspoken” and noted that it “leans more toward personal history than political rallying cry.” Smalls confirms as much when I ask what he wants readers to take from it.

“A lot of people see a piece of themselves inside of me and my story,” he says. “Whether it’s evictions, whether it’s divorce, whether it’s having kids, whether it’s getting fired from a job several times, whether it’s hitting rock bottom — all of that is in the book as well. It’s not just about the success that I had at Amazon. It’s also about the failures I had as well.”

That’s the thread he wants readers to follow. The book moves through his father’s stints in prison, an early Amazon firing for two minutes of “time theft” (he was rehired), a Florida community college he didn’t finish, sound-engineering classes he didn’t finish, a basketball dream cut short by a hit-and-run on the job, an ex-wife and twins, and a brief rap career. He did a showcase with Meek Mill in New Jersey, he clarifies, not a tour. Multiple outlets have gotten this wrong. The cumulative effect is a portrait of a working-class American who happened to be standing where the pressure broke first, not a labor icon.

His mother was a member of the healthcare workers’ union SEIU 1199 for more than twenty-five years and never once mentioned it at home. “She wasn’t like an organizer. She just was a rank-and-file member.” When I ask if he ever imagined this life, he laughs. The skill sets he draws on now, he says, are the ones he watched his mother use to hold down their household. “The grit and the grind that I saw my mom go through, it carried over into the things that I do and how I fight back now.”

The Palestine turn

The Chris Smalls who became famous in 2020 was a workplace organizer. The man in front of me in 2026 is something bigger and less easily categorized. He talks about Gaza, Cuba, ICE, surveillance, and the prison industrial complex as if they’re the same fight.

Last July, he boarded the Handala, a vessel operated by the Freedom Flotilla Coalition, attempting to break the Israeli blockade of Gaza with humanitarian aid. Israeli forces intercepted the ship in international waters. Smalls, the only Black activist on board, was singled out for particularly aggressive treatment, by his account and the accounts of others on the ship. He spent five days in Israeli custody, hunger-striking the entire time, before being released without charges at the Jordan border.

He is now banned from Israel, he says, for 100 years.

The flotilla, he tells me, is what ties it all together. “Once again, connecting the dots with Amazon and genocide was something important to me.” Amazon and Google’s joint $1.2 billion Project Nimbus contract provides cloud infrastructure to the Israeli government and military. “It’s the same technology that’s being used to empower ICE over here,” Smalls says, “and the local police departments and the rain cameras and also the government contracts they have with the Pentagon and the military-industrial complex.”

His argument: the line between an Amazon warehouse worker in Staten Island and a Palestinian under occupation runs through the same cloud server.

He invokes the longshore workers’ creed. “There’s a saying in the labor movement from the ILWU. Injury to one is injury to all. And it doesn’t say injury to one is injury to all except for Palestinians.”

That position has put him at odds with the leadership of the AFL-CIO and the International Longshoremen’s Association, both of which he has publicly accused of complicity in the war. Among nationally known U.S. labor figures, he is more or less alone on this.

Surveillance and sacrifice

I ask him about the cost. He has been arrested in New York, detained in Israel, and most recently stopped by ICE at the U.S. border on his return from a humanitarian aid mission to Cuba.

“My phone was taken by ICE,” he says. As we are speaking, he tells me, a comrade of his has just been detained at JFK airport. The agents are asking him questions about Smalls.

“I’m being surveilled,” he says. “I’m being targeted, of course. I’m being doxxed. It comes with the sacrifice of the work that I have to do, unfortunately. But I ask myself if I don’t do the work, then who else is going to do it?”

He grew up, he tells me, in a context where this was always going to be the cost. “I was in handcuffs by the time I was ten years old. The average Black man has probably been in handcuffs at least once by the time they’re in their thirties. I can sit here and say I’ve been in handcuffs a dozen times, and I probably have a dozen more to go.”

He pauses. “Martin Luther King was arrested, I believe, twenty-nine times. So I’m trying to break his record.”

You can read that line as bravado, or as something more deliberate: a claim to a tradition, a way of locating himself inside a longer arc of Black American resistance. I think he means it both ways.

The institutional reality

The harder question, the one I keep circling, is what all this adds up to institutionally. Smalls is no longer the president of the Amazon Labor Union. His successor, Connor Spence, led the union through the recent National Labor Relations Board ruling that ordered Amazon to bargain. It was the most significant legal victory at JFK8 since the original union vote. Smalls’s old union publicly described his Met Gala arrest as a “lone-wolf direct action” that was not coordinated with leadership.

The arc that landed him outside that institution is worth naming. The ALU Smalls founded in 2021 was conceived as a rejection of established labor. If the big unions had been capable of organizing Amazon, he argued at the time, they would have done it already. By June 2024, that posture had reversed. ALU members voted 98 percent in favor of affiliating with the 1.3-million-member International Brotherhood of Teamsters. The leadership election a month later was won by Spence, who had founded the dissident ALU Democratic Reform Caucus and sued Smalls in 2023, alleging he had refused to hold officer elections in violation of the union’s own constitution. Smalls did not run.

To grasp the distance he has traveled, it helps to remember how high the rise was. In 2022 he was named to the Time 100, fielded statements of solidarity from Bernie Sanders, AOC, and Elizabeth Warren, and watched Amazon’s general counsel hand him a national platform by calling him “not smart or articulate” in a leaked internal memo. His profile from that period is mostly intact. His institutional standing is not. He has no organizational vehicle of his own anymore; The Congress of Essential Workers, the nonprofit he founded in 2020, appears largely dormant. The Teamsters local he now belongs to answers to international president Sean O’Brien, who delivered a primetime address at the 2024 Republican National Convention. Smalls, whose recent advocacy has centered on Palestinian solidarity and a public attack on the AFL-CIO leadership, has not publicly addressed the contradiction.

When I ask how he balances direct action with the slower, more institutional work of organizing, he is generous about both. “Everybody has a role to play. I don’t think everybody has to do the same thing. Whatever you can contribute to the movement, you do that. My skill sets are different. My skill sets have always been direct action.”

“Coalition building is always going to be hard,” he says. “But one thing people know about me, whether it’s 100 people, 1,000 people, or 10 people, I’m going to go forward. No matter who shows up, no matter how many people we get, we still got to show up and do what we can.”

That’s the most honest articulation of where Smalls is in 2026, I think. He’s not trying to run anything. He’s trying to be the person who shows up when whoever is running things can’t or won’t. Whether one man jumping a barricade is any substitute for the patient, unglamorous work of contract negotiation is the open question. It will define his next decade.

He seems aware of it. When I ask what keeps him grounded, he goes back to the warehouse.

“My feedback was Chris has sided too much with the workers,” he tells me. That was the reason Amazon gave for never promoting him to salaried manager, despite forty-nine applications. “And it’s like, yes, absolutely. I’m siding too much with the workers, because I was a worker before I became an assistant manager.”

“The only thing that matters to me,” he says a moment later, “is seeing people get liberated from being oppressed.”

What comes next

We end where these conversations always end, on the question of the future. I ask if he has anything else he wants to say.

“No,” he says. “I mean, this is great. I’m always glad to spread the word and plant seeds. The revolution starts with yourselves.”

The line works as both a book ending and a personal credo. He’s been saying some version of it for years. When the Revolution Comes is out June 1. The bargaining order against Amazon stands. The contract at JFK8 does not yet exist.

Chris Smalls is thirty-seven years old. He has, by his own count, several dozen more arrests ahead of him before he meets Dr. King’s record.

He has time.

Christopher Sweat is a journalist with GrayStak, which covers political and social dynamics in real time across Washington, DC, New York, and Chicago: local, state, and federal politics from the streets to the institutions. The full video interview with Chris Smalls is available on the GrayStak YouTube channel.

When the Revolution Comes: A Fight for the Future of the Working Class is published by Crown on June 1, 2026.

Teta Jalila, c. 1920. The photograph Laila Grace uses as the logo of her design practice.

A conversation with Laila Grace at SAIC Galleries about her thesis, Jalila's Vanity, Palestinian futurism, and the design lineage that runs through her distant cousin Rajie Cook. Full essay below.

If you have ever found a bathroom in an airport, you have used a piece of design produced by a Palestinian Christian from Ramallah.

His name was Rajie Cook. The family name was Sulaiman before Ottoman officials nicknamed his grandfather Küçük, Turkish for small, which the British Mandate Anglicized to Cook. He was born in Newark, New Jersey in 1930, the son of Jalila Totah and Najeeb Esa Cook, who had immigrated from Ramallah three years earlier. An elementary school teacher told him his name was too difficult to pronounce. He became Roger. He returned to Rajie in his older years.

He designed the world we walk through. The DOT pictograms (the standardized symbols for restrooms, telephones, baggage claim, no smoking, escalators, every wordless icon in every American airport, hospital, highway, and federal building) were produced by his firm Cook and Shanosky Associates for the U.S. Department of Transportation. President Reagan and Elizabeth Dole presented him with the Presidential Award for Design Excellence in 1984. The Symbol Signs are now in the permanent collections of the Smithsonian and the Cooper Hewitt National Design Museum.

In his later years, he turned to sculptural assemblage, making small boxes that documented his fact-finding trips through Israel, Jordan, and the West Bank and Gaza as a member of the Presbyterian Church (USA) Task Force for the Middle East. One of those works was exhibited in Made in Palestine in 2003, one of the first major American shows of contemporary Palestinian art. He died in 2021.

His distant cousin, Laila Grace, has just completed her Master of Design in Designed Objects at SAIC, following a BFA in Industrial Design at the University of Illinois at Chicago. She describes herself on her website as “a Palestinian Christian industrial and graphic designer based in Chicago,” with roots in Ramallah Tehta, Birzeit, Jerusalem, and Al-Husun, Jordan. She has organized in the Palestinian liberation movement since 2018, and her practice spans industrial design, graphic and visual communication work for movement organizations, and photography. Her thesis is Jalila’s Vanity, named for her great-great grandmother Teta Jalila: a Falahi peasant-class Palestinian woman from Ramallah Tehta, photographed around 1920 in her best clothing and jewelry. Laila uses that photograph as the logo of her practice.

Rajie Cook’s mother was also a Jalila from Ramallah — not the same woman as Laila’s Teta Jalila, but a relative on a branch of the family neither side has fully traced. The name recurs across the lineage the way names of matriarchs tend to.

Laila Grace is not an emerging Palestinian artist who happens to work in design. She continues a Palestinian American design lineage that ran from Ramallah through twentieth-century New Jersey commercial design through Cold War humanitarian witness, and that runs now through Chicago.

“Oppression is also design”

I met Laila at SAIC Galleries during the final week of Graduate Exhibition Two 2026, the second of the school’s two institutional graduate shows. Jalila’s Vanity sits in the Loop space at 33 East Washington Street, two floors below ground. She speaks the way people who have been organizing in Chicago for years tend to speak: declarative, direct, unbothered.

The first thing she said about her practice was not about art. It was about an undergraduate professor at the University of Illinois at Chicago who, when she asked about industrial design through a multicultural lens, told her that “white people invented design.” She has written about this moment on her own website: “This statement was not only ignorant, but also verified my realization of the need for a more inclusive and diverse approach to design.” She returned for her master’s, she told me, partly out of spite.

“Especially when I went to Palestine that summer,” she said, “I really realized how design is not only in objects, but also how we design a society and a community. Palestinians are very communal people because we design our communities effectively. That’s something people in the West actually really struggle with.”

Her thesis statement followed, offered without prompting:

“Oppression is also design. When we see the occupation, it is not only a political occupation that we see through law and politics, but it’s also architecturally designed: through the wall, through the borders, all sorts of things. So this is also a design issue. It’s design used in a way that’s actually really bad for our society, and we need to use design to create a better future as well.”

The separation wall, the checkpoints, the Area A/B/C carve-up of the West Bank, the settlement road infrastructure, the metal turnstiles at Qalandiya: each is a designed object, produced by identifiable designers, built for a function. The conceptual move Laila is making is to take that observation seriously. If oppression is design, so is its refusal.

The pivot

"Oppression is also design."

She has been making work in this register for years, across more media than her thesis suggests. Her portfolio includes graphic design for the Palestinian movement (t-shirts for the U.S. Palestinian Community Network, the Chicago Palestine Film Festival, Students for Justice in Palestine) alongside her industrial design pieces.

Her undergraduate thesis at UIC was Tea Time Under Apartheid: a table bisected by a partition standing in for the separation wall, with Palestinian cultural beauty laid out on either side. At SAIC she made Your Bombs, Our Leisure, a hookah whose body is shaped as a nuclear bomb, an object she writes “the FBI might expect to find during a raid on an Arab-American household,” pierced through a tray of Palestinian ceramics. She made Nijma, an Eastern-style ottoman using the Al-Khalil (Hebron) star motif. She designed a chess table inspired by Gaza’s chess clubs for children. She has a sustained body of tatreez work, including Tatreez of the Future and Tatreez After Dark. Jalila’s Vanity is the culmination of that tatreez investigation, not its beginning.

She calls this earlier body of work discursive design. The term comes from a real subfield (Bruce and Stephanie Tharp’s writing on objects as arguments) that Laila engages directly. The hookah bomb is discursive in this precise sense: it places the symbols of occupation and the symbols of Arab leisure into a single object and forces the viewer to hold them together.

The pivot that makes Jalila’s Vanity different is that Laila has decided to stop making work that engages Israel at all.

“I found that when I was making objects that were about Israel or about the occupation, about the genocide, it didn’t make people care on the outside,” she told me. “I wanted my work to make people care. I was kind of realizing people still don’t care. So I was shifting my focus more into designing purely for the Palestinian people instead of preaching to the choir or trying to change people’s minds.”

This is not depoliticization. It is a tactical reading of what design can and cannot do in the current information environment. Two years into the genocide in Gaza, she has concluded that further work aimed at convincing outsiders is a misallocation of her practice. Her current work is directed instead to a Palestinian audience.

“The wall is not our symbol,” she said. “We have fantastic artists who have made paintings on it, but the wall is not ours. The wall is not ours, but we use that so often.”

In her artist statement she calls this mode Palestinian futurism. The term gestures toward a small body of contemporary Palestinian work (the films of Larissa Sansour in particular) that imagines Palestinian existence outside the present political horizon. Laila’s futurism is not science fiction. It is the assertion that Palestinian people existed before Israel and will exist after it.

“Being Palestinian actually has nothing to do with Israel whatsoever,” she said. “It actually has to do with our deep rootedness and connection to the land itself.”

The vanity

The piece is made from olive wood, the tree of Palestine. Some olive trees there are five thousand years old. Tatreez (Palestinian cross-stitch) developed in villages as a way for women to depict where they were from, whether they were married, what they hoped for, who their kin were. It is a writing system as much as a decoration.

Each motif on this vanity refers to a specific element of women’s self-care drawn from the land:

* Damascus rose, for rose water on the skin.

* A sea motif, which Laila designed herself by combining two existing motifs, for the mud of the Dead Sea.

* Olive branches, for the oil on skin and hair.

* Khol, for the eyeliner traditionally made from crushed nuts or almonds.

The decoration names the ritual. The vanity is not an image of self-care; it is an apparatus for it.

The title’s double meaning lives here too, and Laila pointed it out herself, slightly amused with herself. Vanity, the piece of furniture, and vanity, the quality. “It’s about us being a little bit vain as well,” she said. “You know, the adjective too matters.” She is claiming the right of Palestinian women to be vain, to take pleasure in their own appearance, to indulge in self-regard.

In her artist statement she puts the politics in theoretical terms: the Zionist occupation has reduced Palestinian femininity to “a disingenuous political spectacle,” in which Palestinian women appear only as objects of others’ political gaze, never as subjects of their own. The vanity inverts that.

I asked her where the spectacle critique came from. She named a class at SAIC on spectacle and photography, and described an early photograph from Zionist political literature: a coastal Palestinian village shot to show only one rundown building, used to argue the land was empty. Technically truthful (there was indeed a rundown building) but framed and cropped to produce a lie.

“That’s a lot of times what we see now through the news,” she said. “We’re seen through this spectacle that’s usually disingenuous, and from outsiders telling us who we are rather than us being able to tell other people who we are. Or actually really just to tell ourselves who we are, and have an intimate moment with ourselves.”

The refusal

I tried, during the interview, to place her work in the lineage of Western feminist thought on the gaze and self-regard. I mentioned Simone de Beauvoir. I gestured at the long tradition that runs through Berger, Mulvey, and Irigaray on the politics of looking.

Laila pushed back.

“I’ll push against that,” she said, “because I believe that self-care is a human right that everyone has. I don’t believe that’s a Western feminist trait. I think we all deserve to live lives that are peaceful, that include self-care, self-love. And honestly, we all deserve that.”

Audre Lorde’s line (”caring for myself is not self-indulgence, it is self-preservation, and that is an act of political warfare”) is the cleanest statement of the politics Laila is enacting. But Laila is not borrowing it. Her claim is different: self-care is universal, Palestinian women have always practiced it, and the work of the vanity is not to import a feminist concept into a Palestinian context but to make visible something Palestinian women have been doing all along.

That is itself a decolonial gesture. The vanity does not need Audre Lorde to underwrite it.

The line of women

We talked about her family. She is named for her two grandmothers, Laila on her father’s side and Grace on her mother’s. Her mother is Genevieve. The vanity is named for Teta Jalila, who appears in that 1920 photograph dressed in her best, jewelry on, in traditional Palestinian clothing, posing for the camera. On her About page Laila writes that she remains “deeply connected to Teta Jalila, who lived in Palestine prior to Israeli occupation,” and “hopeful that my generation will witness a liberated Palestine, and if not, we are committed to raising the next generation who will.”

“This photo strikes me as, okay, this is a beauty icon,” she said. “She’s a beautiful woman in this photo, posing, and I found that very feminine.”

Her grandfather on her mother’s side did graduate work at the University of Chicago in philosophy of history and wrote books on Arab history. She described tea-time conversations with him as formative. Her distant cousin Rajie Cook came up later in the interview.

Underneath all of it sits a claim she stated plainly:

“Palestinian women are the reason we still exist. They pass the language, they pass the culture, the heritage, everything. That’s what really keeps us still on our land and still sturdy and steadfast, because we have more of a connection to this land through these things. That’s why Israel can’t get rid of us.”

What comes next

"Advocating for Palestine in your workplaces, in your schools, are just as important as being in the streets."

I asked her what was next. There are opportunities she has been offered that she is not yet ready to discuss publicly. She intends to keep designing for the Palestinian community.

She said something else at the end of the interview worth holding up:

“Something I’ve really learned in my career is to really trust in yourself and to not be afraid to talk about Palestine in all spaces. I have a normal office job. I took the opportunity to give presentations about Palestine in relation to the fields that I’m in. Advocating for Palestine in your workplaces, in your schools, are just as important as being in the streets. I think both need to happen.”

The street, the workplace, the gallery, the design school: continuous terrain in her analysis. Rajie Cook designed the symbols that taught Americans how to find their way through public space. His distant cousin is designing objects for a different navigation problem.

Jalila’s Vanity is on view through Wednesday, May 20, as part of Graduate Exhibition Two 2026 at SAIC Galleries, 33 E. Washington Street in the Loop, 11 a.m. to 6 p.m. The galleries are open to the public; visitors must present a valid government ID. After Wednesday, it comes down.

Laila Grace’s portfolio is at lailagracedesign.com. She is on Instagram at @pettystinian and @lailagracedesign.

At the Illinois State Capitol, Norma Hernandez broke down the political realities behind how legislation moves through Springfield.

The conversation covered HB2723, progressive revenue proposals like the digital advertising tax, and broader fights over taxation, corporate power, and economic inequality in Illinois. But much of the discussion focused on something less visible from the outside: the internal politics of the legislature itself.

Hernandez explained how lawmakers build support around bills, how coalitions form around specific issue areas, where resistance comes from, and how relationships inside the Capitol shape whether legislation gains momentum or dies quietly in committee.

She also reflected on her entry into state government after being elected in 2023. Coming from a background in social work, urban planning, and policy research, she described the shift from studying political systems to operating inside one: learning the personalities, alliances, and institutional dynamics that define Springfield politics.

The conversation offers a look at how power, negotiation, and political community function inside the Illinois legislature beyond the public-facing debate.

This conversation took place inside the Illinois State Capitol. On its surface, it’s an interview with a policy organizer working on active legislation. More broadly, it offers insight into how some political actors are thinking about the relationship among advocacy, policy, and capital.

At the center is Illinois’ anti-boycott framework and the effort to repeal it. As described in the interview, the law allows the state to investigate whether companies are engaging in politically motivated boycotts and, in some cases, remove them from state pension portfolios. That creates a point of overlap between public investment decisions and political criteria—raising questions about what role pension systems are meant to play.

The implications are contested. The Ben & Jerry’s and Unilever example raised in the conversation reflects one way participants understand the downstream effects: scrutiny can lead to divestment activity, which can then influence pricing, positioning, and, in some cases, corporate decisions. Whether that chain is consistent or situational is debated, but the perception itself is shaping how people engage with the issue.

What stands out is the framing. The approach described links activism, legislation, and economic pressure into a single line of effort. The focus isn’t just on narrative or elections, but on influence that runs through institutions and capital flows.

There are limits. The conversation points to coordination problems—overlapping candidates, fragmented coalitions, and misaligned priorities—that make it harder to convert agreement into outcomes. In that sense, the constraint is often internal as much as external.

Taken together, this reflects a broader shift. Political actors are testing how state-controlled capital can intersect with policy goals, while working through the coordination challenges that come with it. The boundaries between governance, markets, and political strategy are still being worked out.

Most of this is unfolding outside national attention, for now.

Editor’s Note

This interview is part of GrayStak’s ongoing coverage of political movements, governance models, and institutional dynamics in major U.S. cities. The views expressed reflect Alderperson Rodriguez-Sanchez’s perspective and are presented to understand better how power is organized and exercised at the local level.As part of our Chicago coverage, we are speaking directly with policymakers, organizers, and institutional actors shaping outcomes on the ground.The Seat Belongs to the Movement: A View from Inside Chicago’s Grassroots Political Model

I sat down with Alderperson Rosanna Rodriguez-Sanchez in her office at Chicago City Hall to understand how she thinks about power—where it comes from, how it’s built, and how it operates once you’re inside government.

What she laid out is not the dominant framework most people associate with Chicago politics. It is a perspective shaped by multi-generational organizing, community-based mobilization, and a view of governance that differs meaningfully from traditional institutional models.

Early in the conversation, she framed it directly:

“The seat belongs to the movement.”

That idea anchors how she approaches her role. It reflects a view that political authority is not held individually but is temporarily exercised on behalf of a broader base.

Her perspective is rooted in early experience. She described her first protest at six years old in Puerto Rico, when her community lacked running water during a drought. In that environment, organizing was not ideological—it was a practical response to the absence of reliable public services.

“We protested… and the organizing actually worked, and we were able to get our water back.”

From her standpoint, that experience shaped a broader understanding of politics:

“Organizing is fundamental to survival.”

This framing is an important context for her interpretation of governance. It places collective action at the center of political life, in contrast to the more individualistic framing that often dominates U.S. political discourse.

When applied in Chicago, this perspective leads to a different approach to electoral politics. Rodriguez-Sanchez did not come up through traditional party or institutional pathways. Her entry point was through organizing, working with immigrant communities, youth networks, and local movements, before transitioning into elected office.

That background informs how she distinguishes her model from what is commonly referred to as Chicago’s political “machine.”

“We are not the new machine… we are organizing people around issues that are important to people.”

In her view, the difference is structural. Traditional machine politics is associated with patronage and control of resources, jobs, contracts, and institutional leverage. The model she describes is organized around issue alignment and volunteer participation.

That distinction also shapes how she describes political accountability:

“If the organization decides to run somebody else… I step aside.”

Whether or not that model is broadly replicable, it reflects a different conception of incumbency, one where political authority is contingent on continued alignment with an organized base.

Beyond framing, the conversation also surfaced how these ideas translate into governance.

On immigration, she described the development of coordinated response systems to monitor and respond to enforcement activity at the local level:

“We created the Northwest Side Rapid Response System.”

These systems include volunteer networks, legal coordination, and communication channels designed to respond quickly to developments on the ground. They illustrate how local actors can shape the experience of federal policy in practice.

On public safety, her focus has been on expanding non-police responses, particularly for mental health crises:

“We need to center care, not violence.”

This includes efforts to build out mobile crisis response teams and strengthen public mental health infrastructure. This approach reflects a broader shift in how some local governments are thinking about safety and service delivery.

On economic policy, she pointed to ongoing tensions around taxation and revenue generation:

“Rich people never want to pay their fair share.”

Here, her comments reflect a broader dynamic visible in many cities where efforts to restructure revenue or shift fiscal priorities encounter resistance from well-resourced stakeholders.

From a GrayStak perspective, what stands out is not just the substance of any single position, but the underlying model of how power is organized and exercised.

The structure she describes is networked rather than centralized, linking local organizations, elected officials, and, at times, state and federal actors into coordinated systems. Information, resources, and response mechanisms move across those layers in ways that are not always visible from the outside.

This matters in a broader context.

Major U.S. cities are increasingly serving as primary arenas in which national political tensions are operationalized. Immigration enforcement, public safety, housing policy, and taxation are not just federal debates—they are implemented, adapted, and contested at the local level.

In that environment, the composition and orientation of local leadership can materially shape outcomes.

As she put it:

“It matters who is in these seats.”

That statement can be read in multiple ways—politically, operationally, and analytically.

From an analytical standpoint, it reinforces a broader point: understanding political and policy risk in the U.S. increasingly requires close attention to local systems, not just national narratives.

What this conversation provides is direct access to one such system—from the perspective of a policymaker who operates within institutions while being shaped by organizing traditions outside them.

It is not the only model in operation. It exists alongside more traditional structures—capital-backed networks, institutional coalitions, and established political hierarchies.

But it is an active one. And in cities like Chicago, where national tensions are translated into local outcomes, it is increasingly part of how power is actually being built and exercised.About GrayStak

GrayStak is a media and political risk platform focused on emerging instability, institutional dynamics, and political movements across the United States. Combining on-the-ground reporting with structured analysis, we identify early warning signs and turn real-world events into actionable insights for public, corporate, and institutional decision-makers.

National attention around the race for Illinois’ 9th Congressional District has begun to grow. Veteran political strategist David Axelrod recently pointed to Kat Abughazaleh as a candidate drawing unexpected attention — a sign that what began as a relatively unconventional campaign is now entering broader national political conversation.

Abughazaleh’s run has broken with many of the traditional norms of congressional campaigning. Rather than focusing primarily on donor networks, formal party infrastructure, and traditional advertising, her campaign has emphasized community events, live performances, concerts, and mutual aid initiatives to embed itself more deeply in the district's daily social life.

A major pillar of her strategy is digital organizing. Abughazaleh describes building an online political community through platforms like Discord, where supporters can interact directly with the campaign, coordinate volunteer efforts, and participate in discussions that shape messaging and priorities. The model reflects a broader shift in how younger campaigns are attempting to maintain constant accessibility and build participatory political communities that exist both online and offline.

At the same time, the campaign has been accompanied by controversy. In our conversation, Abughazaleh addresses the indictment that has become part of the public narrative surrounding her candidacy and discusses how she believes it has shaped perceptions of the race. She also reflects on the ways traditional polling can struggle to measure candidates who build support through decentralized networks rather than conventional campaign infrastructure.

Beyond the mechanics of the campaign itself, the discussion also turns to the broader political landscape. Abughazaleh shares her perspective on the Democratic Party, evolving voter expectations, and how candidates experimenting with new organizing models may influence the future of congressional politics.

For observers of political movements, the campaign offers an interesting case study in how modern campaigns are evolving at the intersection of digital infrastructure, community organizing, and political storytelling.

Below is the full interview in which Christopher Sweat sits down with Kat Abughazaleh to discuss her campaign, her strategy, and the broader political environment shaping the race.

GrayStak conducts independent field reporting and interviews across American political movements, elections, and political conflicts — documenting the people, strategies, and events shaping the country in real time.

I sat down with Karina Villa for a 39-minute discussion about her campaign for Illinois Comptroller and her broader vision for the office.

Villa frames her candidacy around what she calls a “true progressive” approach to fiscal oversight. In our conversation, she makes clear that she sees the Comptroller’s statutory responsibilities — paying the state’s bills, maintaining transparency, and safeguarding financial stability — as foundational. But she also argues that the office carries a public platform that can be used more actively.

A recurring theme in the interview is the idea of the Comptroller’s “microphone.” Villa describes the role not only as a financial administrator, but as an additional voice within state governance — one capable of elevating concerns she believes may not always surface through the Governor’s office or other executive channels. She positions this approach as a way to connect fiscal oversight with the lived realities of Illinois residents.

The Democratic primary for Comptroller is competitive, and while Villa does not name opponents directly, she draws distinctions in philosophy and tone. She emphasizes accountability, transparency, and what she describes as a closer alignment between financial stewardship and community priorities.

The conversation explores how she balances technical competence with advocacy, how she interprets the boundaries of the office, and why she believes this moment calls for a more visible and engaged Comptroller.

As always, this interview is presented without endorsement and is part of GrayStak’s ongoing effort to document and examine state-level leadership and governance debates in depth.