Getting asylum in Chicago is nearly impossible

Good morning, Chicago. ✶

🔎 Below: Asylum was historically difficult to obtain for immigrants in the U.S. But since President Donald Trump returned to office, a shake-up at immigration courts in Chicago has made it nearly impossible.

🗞️ Plus: A new parking meter deal advances, Chief Keef’s homecoming and more news you need to know.

📝 Keeping score: The White Sox clinched a playoff spot with a 9-1 win over the Royals. The Cubs are also headed to the playoffs after beating the Marlins 2-1. The Sky lost to the Mystics, 101-93.

⛅ Today’s weather: Mostly cloudy with a chance of showers and a high near 67.

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⏱️: An 8-minute read

TODAY’S TOP STORY 🔎

It’s now nearly impossible to get asylum in Chicago immigration court

By Lauren FitzPatrick, Adriana Cardona-Maguigadand Keenan Chen

Major shake-up: Since January 2025, President Donald Trump’s Department of Justice has foisted a major shake-up onto immigration court. Veteran judges have been pushed out and replaced by new hires. A national social media campaign to recruit new judges continues to frame the role as a “deportation judge.”

In Chicago: Here, many of the recent hires used to work in military and administrative law, rather than immigration law, taking the bench largely without important context about the home countries immigrants have fled. Immigration judges have also been saddled with heavy caseloads, narrowed rules aimed at granting fewer asylum cases, and a new urgency coming from Washington to wrap up cases for migrants from certain countries, lawyers and ousted judges say.

Key context: Asylum is historically a hard-won way to stay in the U.S., requiring evidence of persecution back home that specifically targets protected groups of people, such as political dissidents or ethnic minorities.

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EDUCATION 🍎

Anthony Vazquez/Sun-Times

CPS enrollment drops again

By Nader Issa

Enrollment declines: Chicago Public Schools enrollment has declined once again by another 11,500 students to about 304,700, officials said, the lowest number in more than two decades.

Key context: Declining enrollment — and, subsequently, underenrolled schools — have become a key issue in the city’s first-ever school board president race as some candidates suggest revisiting school closures. The district has a moratorium on closings until after this school year.”

The reasons: CPS officials are pointing to declining birth rates locally, nationally and globally, in addition to families leaving the city for the suburbs and immigrant population declines spurred by President Trump’s aggressive deportation policies.

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CITY HALL ✶

Committee backs $2.5B sale of parking meters

By Fran Spielman

Deal OK’d: The City Council’s Finance Committee on Thursday approved New York investment firm Stonepeak Partners’ $2.53 billion bid to acquire Chicago parking meters, along with a compromise aimed at making the widely despised meter deal less onerous for taxpayers.

Key context: In 2008, Mayor Richard M. Daley decided to lease Chicago parking meters to private investors for 75 years. Finance Chair Pat Dowell (3rd) on Thursday said investors from as far away as Abu Dhabi have recouped their $1.15 billion investment two-fold with 57 years still left on the deal.

What’s next?: The sale to Stonepeak and the compromise attached to it still must be approved by the full City Council.

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MORE IN COURTS ⚖️

Sally Ryan for The New York Times

• Prosecutor retires: Sheri Mecklenburg, the federal prosecutor at the center of the “Broadview Six” scandal, announced her retirement, insisting that she “owns” her mistakes in the tainted case, even as she accused the former defendants of trying to “smear her with meritless accusations.”
• Funeral home inspection ordered: A judge ordered another inspection of the South Chicago Chapel, where 56 decomposing bodies were found last month. The funeral home operators, Clark and Johanna Morgan, were also barred from using, renting or leasing the building.
• Man sentenced in biker club beating: While prosecutors had wanted at least two years in prison for the Calaveras Motorcycle Club’s Julio C. Salas, a judge sentenced him to 180 days, and with time served, he was able to walk free.
• City vs. police union: Lawyers for the city and its largest police union faced off Thursday before the Illinois Supreme Court, arguing over the handling of disciplinary hearings for officers accused of egregious misconduct.

MORE NEWS YOU NEED 🗞️

• Trump visit prompts protests: Roughly 100 protesters gathered Thursday near the Medinah Country Club in DuPage County, where President Trump is expected to appear this weekend for the President’s Cup golf tournament.
• Security strikes teen at mall: A security guard at the now-shuttered Ford City Mall has been accused of hitting an 18-year-old with his vehicle Monday night after allegedly battering a man with a metal rod in an incident captured on video, according to Chicago police.
• Benches on the way: After a man built wooden benches by bus stops on the Northwest Side, highlighting the need for seating, the city has taken notice and will replace them with ones up to municipal code.
• Things to do Sept. 25-30: The African-Caribbean International Festival of Life and the Jerk, Seafood and Vegan Festival combine, plus Andersonville Arts Weekend and the Armitage County Fair are among the highlights.

MUSIC 🎶

Candace Dane Chambers/Sun-Times

Review: Chief Keef’s homecoming show falls short

Review by Mark Braboy

Artist’s return: After more than a decade of being unofficially blacklisted by Chicago-area venues, Chief Keef finally returned Wednesday to his hometown. But while the ambition was there, the execution was not, as his homecoming show fell short of the sky-high expectations.

Major moment: Originally scheduled for Sept. 12, the concert was one of the most anticipated moments in Chicago hip-hop history, with Keef kicking off his headlining national tour in Chicago.

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ON WBEZ 91.5 FM 📻

In the Loop with Sasha-Ann Simons, 9 a.m.

• Weekly news recap: WBEZ’s Cheryl Raye-Stout, Chicago Tribune’s Jake Sheridan and NBC 5’s Christian Farr join the show to break down the week’s top stories.

Say More with Mary Dixon and Patrick Smith, 10 a.m.

• Skin care: Dr. Lauren Fine of the American Academy of Dermatology stops by with advice as callers weigh in.

LISTEN LIVE 🎧

FROM THE PRESS BOX ⚾

Cubs and Sox clinch the playoffs in historic moment

By Vinnie Duber and James Fegan

History made: For the first time, the Cubs and the White Sox have, on the same day, both secured postseason berths — two minutes apart.

PCA’s 40-40 season: An MVP favorite, the Cubs’ Pete Crow-Armstrong on Thursday secured the seventh 40-homer, 40-steal campaign in baseball history.

Cubs back at it Tuesday: As the champagne and beer flowed in the Cubs’ clubhouse Thursday, Tuesday’s opening-round, best-of-three series loomed. “There’s a lot still to be done,” starting pitcher Matthew Boyd said.

Sox’ big moment: In a season with 11 walk-off victories, 35 come-from-behind wins, 31 usages of an opener, and countless defied expectations, the White Sox have now reached their first playoff berth in five years. They’re also the first team in MLB history to reach the postseason on the heels of three-straight seasons of 100 losses or more.

What’s next?: The Sox say they’re prioritizing rest and the division race as they set their final rotation order.

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WATCH: CUBS AND SOX CELEBRATE ▶️

CHICAGO MINI CROSSWORD 🌭

Today’s clue: Cubs player Moisés, who was involved in the Bartman Ball incident.

PLAY NOW

BRIGHT ONE 🔆

Anthony Vazquez/Sun-Times

Lil Rel comes home for a meaningful laugh

Reporting by Mike Davis

Comedian Lil Rel Howery has come a long way from the West Side and his early days as a standup comic here. But lately, he’s spent a lot of time on screen, with credits that include a role in Jordan Peele’s Academy Award-winning film “Get Out,” NBC’s “The Carmichael Show” and even his own sitcom, “Rel” on FOX.

Now, he’s coming home. Last weekend, Howery filmed his latest standup special at Black Ensemble Theatre. The homecoming show is part of the What’s Funny Comedy Festival, running through Saturday, which Howery cofounded with his former manager, Knowledge Beckom.

“Everything I’m doing the next few weeks in Chicago — the comedy festival, and I’m shooting a limited series that I wrote and created — it’s a love letter to my family. It’s my love letter to Chicago and to the way I grew up,” Howery said.

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YOUR DAILY QUESTION ☕️

What’s something every Cubs and Sox fan can agree on?

Reply to this question via email (please include your first and last name). We may run your answer in a future newsletter or story.

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Written and curated by: Matt Moore
Editor: Michael Lansu