🚨 Chicago 312:

Chicago 312 is a weekly newsletter that explains what actually happened in Chicago politics this week, including, sometimes, the lies. Every Thursday: 3 Headlines that name the real stakes, 1 Big Question about power and legitimacy, and 2 Red Flags about what everyone's getting wrong. Subscribe here.

It's only mid-January, can you believe it?

Other questions with no answer from the ongoing terrible news this week: Can sanctuary cities survive federal siege? Do oversight bodies have any actual power?

Here's what happened, let’s get into it:

3 Headlines:

1. Trump's Feb 1 Funding Threat: $3 Billion on the Line

Block Club Chicago, CBS Chicago, ABC7: On Tuesday, Trump announced he's cutting all federal funding to sanctuary cities starting February 1. For Chicago, that's roughly $3.5 billion in federal grants annually—the city directly spends about $1 billion of that each year on transit, public safety, aviation, and basically everything that keeps the city running. Mayor Johnson's response: "We'll see you in court."

This isn't Trump's first rodeo threatening sanctuary cities, and legal experts say this time might stick. Northwestern law professor Nadav Shoked told CBS that if the administration targets specific grant categories with looser rules—like discretionary transportation funding—they might have more legal cover than in previous attempts.

Trump's team is getting savvier about which pots of money they can actually withhold without violating congressional authority, including $2.1 billion for the CTA's Red Line Extension and Red/Purple Modernization back in October—contractually obligated funds that Senators Duckworth and Durbin say are being illegally withheld.

Why It Matters: Chicago pays more in federal taxes than it gets back, and the city's entire sanctuary infrastructure depends on whether Johnson and Pritzker can actually make the "we'll sue" threat costly enough to matter. The administration knows Chicago can't replace $3 billion. If courts don’t move fast enough to stop the bleeding, Chicago watches transit projects die, violence prevention programs collapse, and federal leverage turn sanctuary policy into a blunt object for punishing cities.

2. 1,000 Chicagoans Pack Pilsen Meeting, CCPSA Chooses Inaction

The Triibe, South Side Weekly, WTTW, Chicago Tribune: On January 8—one day after ICE agent Jonathan Ross shot and killed Renee Nicole Good in Minneapolis—over 1,000 Chicagoans flooded Thalia Hall in Pilsen for a Community Commission for Public Safety and Accountability (CCPSA) listening session.

CCPSA is the civilian oversight body created in 2021 after decades of organizing—it has the power to set CPD policy, demand answers from the superintendent, and with a two-thirds vote, begin removal proceedings. The meeting happened only after 2,000+ residents signed a petition demanding investigation into CPD's collaboration with ICE during Operation Midway Blitz.

Residents gave testimony of CPD officers forming protective perimeters around ICE agents (explicitly banned by Illinois' TRUST Act), preventing rapid responders from following agents, arresting protesters, using CPD helicopters to assist federal convoys, and in one case, hugging a Border Patrol agent.

The most damning evidence is from December 17, when Border Patrol commander Greg Bovino called 911 claiming he was being attacked. CPD activated a helicopter, pulled over a rapid responder following the federal convoy on Lake Shore Drive, and gave him a "verbal warning." Bovino then posted on social media thanking Chicago police for their "assistance."

The CCPSA's response? CCPSA Vice President Angel Rubi Navarijo told the crowd, "We need to trust our police department." The audience booed.

CCPSA President Remel Terry said the commission was "actively working" on the issue but needed more time to organize a hearing with all 22 district commanders. District Council members—including Leonardo Quintero (12th PDC) and Elianne Bahena (10th PDC, also Ald. Mike Rodriguez's chief of staff)—had sent a letter on November 13 requesting a formal hearing. That was 218 days after the first documented CPD-ICE interaction on June 4. The commission told them spring at the earliest.

As Kayla Nguyen with the Chicago Alliance Against Racist and Political Oppression said: "Trump doesn't need the National Guard if we have the Chicago Police Department allowing ICE into their facilities, clapping federal agents on the back, our local law enforcement giving them hugs and snacks."

Why It Matters: CCPSA has the power to draft policy, haul Superintendent Larry Snelling before the commission, and with a two-thirds vote of no confidence, begin the process to remove him. But who actually has the authority to arrest Bovino when he's publicly thanking CPD for violating the Welcoming City Ordinance? Who can enforce sanctuary policy when CPD collaborates with federal agents? City officials admitted in June it was "unclear which agency had the authority to probe" CPD's compliance.

So you get an oversight body created by years of organizing, with limited formal powers on paper, that also won't move fast enough to matter when federal agents are actively operating in the city. The crowd knew it. That's why they booed.

3. Edgewater NIMBYs Sue to Kill Transit-Oriented Density

Block Club Chicago, Chicago Sun-Times, The Real Deal: Months after City Council approved upzoning a 1.5-mile stretch of Broadway in Edgewater and Uptown, a group calling itself "Edgewater Residents for Responsible Development" filed a lawsuit Monday asking a judge to reverse the decision.

The rezoning, passed in October with support from Alders Angela Clay (46th), Matt Martin (47th), and Leni Manaa-Hoppenworth (48th), allows buildings up to 80 feet on most of Broadway between Devon and Montrose. The goal: create more housing on a Red Line corridor where prices have spiked and gentrification pressure is mounting.

The neighbors' group, led by president Patricia Sharkey, says the upzoning was "unprecedented both in terms of distance covered and sheer number of properties affected." Sharkey told the Sun-Times: "The complaint that the community has had for over a year is that there was no study and there was no planning. [The city] jumped to zoning as their plan, and it came from Downtown instead of coming from the community."

Why It Matters: This was one of Mayor Johnson's rare wins with the real estate community—a transit-oriented development push that actually passed Council. Now it's in court, where wealthy homeowners are trying to weaponize procedural requirements to kill density on a transit corridor during a housing crisis. If the lawsuit succeeds, it sets a precedent that procedural challenges can reverse any upzoning, no matter how many progressive alders support it.

And in terms of "community input"—there was intense neighborhood debate. The public hearing was so packed they used a lottery for speakers. The complaint isn't that there wasn't engagement. It's that the result didn't go their way.

1 Big Question:

Can Chicago's institutions enforce sanctuary status when the feds are actively trying to bankrupt them into compliance?

Chicago's sanctuary infrastructure was built for a different fight—one where courts moved faster than budget gaps, where the city had enough fiscal cushion to absorb punitive cuts while litigation played out.

But Trump's team learned from the first term. They're picking grant categories with looser rules, timing cuts to maximize chaos, and betting that sanctuary cities can't sustain legal battles and service cuts and political pressure all at once.

So the question isn't whether Chicago wants to be a sanctuary city. It's how Chicago can QUICKLY build the institutional capacity—legal, fiscal, political—to make sanctuary status mean something when the federal government is weaponizing budget cuts.

2 Red Flags:

🚨 Illinois Prisons Can Now Digitize All Inmate Mail, Despite Zero Evidence It Works

NPR Illinois, Capitol News Illinois: On Friday, the Joint Committee on Administrative Rules allowed the Illinois Department of Corrections (IDOC) to make permanent an emergency rule that scans and digitizes all mail sent to people in custody. Incarcerated people now read letters from loved ones on tablets instead of holding the real thing.

The rule was introduced under pressure from Republican legislators and the corrections workers' union after substance exposures in fall 2024 left staff hospitalized. It's been in effect on an emergency basis since August. The department says it's necessary to keep drugs out of prisons. Advocates say there's no evidence mail scanning actually reduces contraband.

The kicker: In IDOC's initial rule proposal, there's a line asking the department to list "any published studies, reports or sources of underlying data upon which the rule is based." The reply: "None." A law signed by Pritzker last August will require IDOC to publish annual data on contraband sources starting in 2027—but IDOC says it's already "confident in its understanding" of where contraband comes from. Which is weird, again, because there’s no evidence.

Why It Matters: Incarcerated people lose the ability to hold letters from their kids, privacy concerns about third-party vendors scanning legal mail are waved away, and families are told to trust that tablets are the same as physical connection on an emergency rule.

🚨 Springfield Returns with an "Affordability" Message and a $2.2 Billion Deficit

Chicago Tribune, Capitol News Illinois: Illinois lawmakers returned to Springfield this week facing a $2.2 billion budget hole and an election-year strategy built entirely around "affordability."

House Speaker Chris Welch: "Everything's going to come down around affordability issues. I think folks are concerned about their homeowners' insurance, their car insurance. Listen, everything's about affordability and that's going to be our focus."

Illinois has a structural revenue problem. Welch has renewed calls for a millionaire surcharge—an idea that polls well and is popular with progressive Dems—but it's "politically fraught in an election year." State Rep. Will Guzzardi, a budget negotiator: "I think we need to invest in our schools and our communities and (lower) property taxes and (provide) social services for people, and we simply don't have the capacity to do all that within the current budget constraints."

Meanwhile, Gov. JB Pritzker just told everyone the graduated income tax is "not a priority" for 2026, despite spending $58 million of his own money in 2020 to try and pass it, ie, he's running for president and doesn't want to be "the tax guy."

Why It Matters: Democrats are running on "affordability" while facing a $2.2B deficit, federal cuts that just froze $1 billion in childcare funds, rising property taxes hitting South and West Side homeowners hardest, and State Farm hiking rates 27%.

That's it this week.

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Quick note: Starting next week, Chicago 312 moves to Thursday mornings. Same analysis, better timing. See you Thursday, Jan 23.