Welcome to Chicago 312: 3 Headlines. 1 (Extremely Long) Big Question. 2 Red Flags. Subscribe here.

What’s up — the sun is out past 5 PM and Greg Bovino was demoted.

Let’s take the small wins where we can.

Tom Homan showed up in Minneapolis so in spite of myself I did a deep dive of his cursed history, including his bipartisan family separation policy advocacy, his closed-door meetings with Chicago Republicans, and the internal White House power struggle between him and Kristi Noem.

Here’s what else happened this week.

3 Headlines:

1. CPD Body Cam Footage Shows Coordination With ICE

Sun-Times: Chicago's Committee on Immigrant and Refugee Rights reviewed body cam footage Tuesday showing a CPD deputy chief directing federal agents where to park transport vans during a June 2025 ICE raid at the South Loop immigration office.

City officials initially claimed CPD "wasn't aware a raid was taking place" when they arrived. Once officers realized federal immigration enforcement was underway, they said cops "moved outside of the facility and provided public safety traffic control."

The body cam footage suggests otherwise. Committee chair Ald. Andre Vasquez (40th) said it "appears to indicate some level of coordination between ICE and officers at the scene." But because there's been no formal investigation, Vasquez said "it's difficult to determine if sanctuary policies were violated."

The committee advanced an ordinance Tuesday empowering the Civilian Office of Police Accountability (COPA) to formally investigate officers accused of violating Chicago's Welcoming City Ordinance, which restricts police cooperation with federal immigration agents. COPA's interim chief administrator LaKenya White said the agency has received about 40 complaints related to ICE interactions—28 of which are possible sanctuary ordinance violations. Watch this video recap — or this one from Families Chicago.

Why It Matters: Chicago’s sanctuary law has no mechanism to hold CPD accountable when they violate it. COPA exists but hasn't opened investigations until now. You need both the law AND the body that can investigate, charge, and punish violations. The ordinance approved Tuesday creates that enforcement path, finally. Whether it actually passes it is the next test.

2. Did That South Shore Landlord Call ICE to Clear Building?

Sun Times: The Illinois Department of Human Rights just filed formal housing discrimination charges against the owners of 7500 S. South Shore Drive investigating claims the landlord tipped off federal agents about Venezuelan immigrants in the building "as part of an attempt to intimidate and coerce the building's Black and Hispanic tenants into leaving."

A flashpoint in Trump's deportation blitz (btw, it cost over 21 million to send the National Guard) DHS raided the building in the middle of the night, with witnesses seeing children separated from mothers, freezing in the September cold without clothes, and many detained for hours. One resident hid his neighbor and her 7-year-old daughter in his room to protect them from agents.

In 2024 alone, building management filed 25 evictions against tenants, more than the previous four years combined, with most owing $900-$1,050 monthly rent. Last month, the remaining residents were forced out after the 130-unit complex was foreclosed—along with two other South Side buildings owned by Trinity Flood, a Wisconsin real estate investor.

The investigation will determine how convenient this particularly raid was for a failing investor ready to do whatever it took to get rid of tenants.

Why It Matters: A Wisconsin investor with failing South Side properties suddenly has federal agents doing the dirty work of tenant removal. I wish I had deeper analysis here — prosecute! 

3. Municipal Bonds Are So Hot Right Now (If You’re Already Rich)

The New York Times: Bear with me on this one, gang, I’m no municipal finance expert, but I’m making an attempt. This deep dive into municipal bond issuance shows Illinois planning to issue $2.1 billion in bonds for capital projects in fiscal 2026—up from $1.3 billion the year before, with Moody's upgrading Illinois's credit rating to A territory in October 2025, the state's highest mark in over two decades. Pritzker's office celebrated: "Not long ago, Illinois was facing repeated credit downgrades, mounting unpaid bills and some of the highest borrowing costs in the country."

This is a hot market: JPMorgan estimates municipal bond yields hit over 7 percent after tax advantages, compared to 4 percent for Treasury notes, and Trump himself bought $100 million in municipal bonds between November and December.

Why It Matters: Chicago's budget fights exist inside this larger story. The city is still dealing with $20+ billion in unfunded pension liabilities while the state gets credit upgrades for not defaulting. The muni bond boom means Illinois can borrow more cheaply than it could five years ago—which is good for infrastructure projects but doesn't solve Chicago's structural revenue problems.

The upgrade came from "disciplined budgeting and responsible financial management," per Pritzker's spokesman. But that discipline involved not taxing the rich—which is why Illinois still faces a $2.2 billion budget gap this year despite the credit upgrades. The state looks good to bond investors because it's been fiscally conservative. Which means the pressure on Chicago to balance budgets without progressive revenue will continue, regardless of how hot the muni market gets.

Municipal bonds work great if you're a wealthy investor looking to shield income from taxes. They work less well if you're a city trying to fund services without adequate state revenue sharing.

1 Big Question: Who is Tom Homan, and What Does He Mean for Chicago?

Unfortunately, Chicago know Bovino’s replacement, Tom Homan, well: between 2013-2016, Homan's team deported over 920,000 people—earning him Obama's 2015 Presidential Rank Award for his ‘effectiveness’.

Atlantic journalist Caitlin Dickerson calls Homan the "intellectual father" of family separation policy. When pitching it to then-Homeland Security Secretary Jeh Johnson, Homan acknowledged families would suffer. Starting in 2014—under the Obama administration—Homan began arguing that separating children from their caregivers would deter illegal border crossings. At the time, the Washington Post wrote: "Thomas Homan deports people. And he's really good at it."

Then, under Trump, Homan’s career really took off: Trump adopted the same plan he advocated for under Obama, in 2018. More than 5,500 children were separated from their parents that year.

After leaving ICE in 2018, he joined Fox News as a commentator, signed with the Heritage Foundation in 2022, and built connections to Southern Poverty Law Center-designated hate groups like ACT for America, an anti-Muslim hate group that organized "March Against Sharia" events. He also, like every ambitious fascist, contributed to Project 2025 (which, for those resilient enough to be still keeping track, the administration is about halfway through fully implementing).

At July 2024's National Conservatism Conference, Homan promised: "If Trump comes back in January, I'll be on his heels coming back, and I will run the biggest deportation force this country has ever seen. They ain't seen shit yet."

Only a few months later in September 2024, Homan was recorded accepting a bag with $50,000 in cash from undercover FBI agents posing as border security contractors seeking government contracts if Trump won.

In September 2025, the Justice Department closed the investigation, citing insufficient evidence that Homan agreed to perform specific official acts in exchange for money—and noting he wasn't in government at the time of payment.

Setting the Stage for Chicago

On December 9, 2024, Homan told Chicago Republicans: "We're going to start right here in Chicago, Illinois." And last year he complained to CNN that Chicago residents are making his job too difficult: "Chicago, very well educated. They've been educated how to defy ICE, on how to hide from ICE. They call it 'Know Your Rights.' I call it how to escape from ICE." He said he's willing to play "a cat and mouse game" until "every one of them gone." But Homan has been doing more than threatening Chicago—he’s been actively recruiting.

According to the Southern Poverty Law Center, he’s held closed-door meetings brokered by Terry Newsome—a Proud Boys associate—and well known Right Wing Influencer and occasional Alder Raymond Lopez.

Homan apparently also met with some Democratic politicians less interested in X fame, who "wish[ed] to remain anonymous."

Lopez—who this month tried and failed to gut Chicago's sanctuary ordinance 39-11—posted after meeting Homan: "We must enforce the laws, starting with removing those committing dangerous, violent crimes."

According to WTTW, Lopez said Homan told him that without local cooperation, agents would have to arrest "long-term undocumented who are doing right in our city" alongside criminals.

Why It Matters: Homan's arrival is an escalation, even if it’s a move away from the embarrassing Gestapo cosplay and viral videos that marked Bovino’s time in power: the shift from short-term raids to long-term infrastructure means local vigilance, especially against sellouts like Lopez matter more than ever.

2 Red Flags: 

🚨  Staying Up on The Internal Drama: Noem v. Homan

Axios: Bovino’s dismissal sets a new stage, with Homan headed to Minnesota and bypassing “ICE Barbie” Noem's chain of command entirely — it’s worth reading more about the dynamics between Homan and Kristi Noem. The overall vibe is illuminating, , though I’m not necessarily advocating for paying MORE attention to the psychological profiles of these miserable people. But in order to better understand the stakes, self interest, and leverage of all these terrible irrational actors, it helps to understand what they think they’re actually trying to do in their pursuit of evil. As one adviser said, Trump enjoys this conflict: "He kind of likes people competing against each other. He thinks it makes the product better." I hope both sides lose.

🚨What the Hell Are Young Men Doing on the Internet?

Garbage Day: As a person who struggles to articulate how my own ‘social listening’ strategy works, or say, articulate what exactly “looksmaxxing,” is and why it matters to my clients, I really enjoyed this piece, primarily about the “regular dude” internet. Garbage Day is expanding their work with political candidates in the world of ‘social interpretation’ - beyond fake metrics like sentiment analysis or a bunch of useless dashboards. Worth a read.

That’s it this week.

I missed these esteemed hard hitting local journalists speaking last night, including Greg Pratt — I hope someone asked if they think Greg Bovino’s Hans Landa impression was on purpose or if he is just that creepy naturally.

One more link: CTA bus drivers being charming while talking about the hardest routes to drive in the city.

Stay safe out there.

BONUS — I am sharing this meme one more time because I think it’s hilarious and I refuse to let the algorithim tell me otherwise.