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Happy Thursday. Start your morning with an investigative report from WTTW News’ Blair Paddock. Plus, more stories about your city. |
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An Immigration and Customs Enforcement vehicle is pictured in Chicago in an image uploaded to social media by the agency on Sept. 8, 2025. (Credit: ICE) |
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As federal immigration agents continue daily raids across Chicago and its suburbs, at least 17 sheriff’s offices across Illinois were found to be contracted to detain people on behalf of Immigration and Customs Enforcement.
Those agreements are in apparent violation of the state’s TRUST ACT, which explicitly prohibits law enforcement agencies from entering into or renewing intergovernmental service agreements to house or detain individuals for federal civil immigration violations. Agencies with an existing contract were legally required to terminate it by Jan. 1, 2022.
“These contracts appear to contravene the Illinois TRUST Act,” said Jonathan Manes, senior counsel for the MacArthur Justice Center, who has been monitoring compliance with the act. “These appear to contemplate that ICE could house people in county jails.”
To ascertain if county jails are complying with the state’s TRUST Act, WTTW News sent Freedom of Information Act requests to each of the 90 county jails in Illinois to obtain copies of intergovernmental agreements with the U.S. Marshals Service.
Some backstory:
Hi, reporter Blair Paddock, here. When reporting on the sheriff in Adams County collaborating with ICE, I came across a Marshals Service contract that included a carve out for ICE to detain people. So, I wondered, how many other sheriff’s departments across the state also have these contracts?
Since August, I have sent 104 Freedom of Information Act requests to sheriff’s offices across the state asking for these contracts. Every office got back to me, and 17 sheriff’s offices had the ICE inclusion. It is unclear if or how often the ICE rider on these 17 contracts have been utilized by Illinois sheriffs.
Either way, a lawyer I spoke with found that checked-off box concerning.
“These counties have put themselves in a potentially very awkward position if ICE comes knocking to hold a detainee,” said Jonathan Manes, senior counsel for the MacArthur Justice Center.
And some sheriffs found it concerning as well: at least four of the 17 have said they will terminate their agreements with ICE after being contacted by WTTW News.
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Military personnel in uniform, with the Texas National Guard patch on, are seen at the U.S. Army Reserve Center, Tuesday, Oct. 7, 2025, in Elwood, Ill., a suburb of Chicago. (AP Photo/Erin Hooley) |
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The Trump administration and attorneys for the state of Illinois agreed to extend an order banning the deployment of some 700 National Guard troops statewide, but that decision could be upended at any moment by an ongoing appeal to the U.S. Supreme Court.
In a phone hearing Wednesday, attorneys for both sides said they had consented to extend a temporary restraining order halting that deployment sought by President Donald Trump until a final judgment is issued in a lawsuit brought by Illinois and Chicago officials.
But regardless of that extension, the order, also known as a TRO, could be overturned at any point after the Trump administration asked the Supreme Court to throw it out. The high court is expected to rule in the coming days.
More context:
The initial TRO, filed earlier this month, was set to expire Thursday.
In a status report filed Tuesday, attorneys for the Trump administration said they initially agreed to extend that existing order by an additional 30 days through Nov. 24. But in court Wednesday afternoon, they proposed leaving the TRO in place until “final judgment” in this case.
They did so, according to the report, in order to “facilitate the Supreme Court’s review of defendants’ stay application” after the Trump administration appealed to the high court in an effort to overturn the TRO.
U.S. District Judge April Perry — who issued the TRO — acknowledged Wednesday morning this case is moving “very quickly,” and while a 30-day extension of that restraining order would provide “a little extra breathing room,” it wouldn’t be “a ton.”
She also recognized the proceedings could be radically altered or rendered moot by the Supreme Court’s pending ruling. |
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Historic Sears Sunken Garden dates back to 1907 and was designed as a place for Sears employees to take a break and enjoy some fresh air, without ever leaving the company's sprawling campus. (Patty Wetli / WTTW News) |
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It's been 50 years since Sears traded in its sprawling headquarters campus on Chicago's West Side for a tower in the Loop. But the retail giant's legacy still looms large in North Lawndale, where the community has, bit by bit, reclaimed pieces of Sears history and turned the story of abandonment into an opportunity for reinvention. Next up on the restoration agenda: historic Sears Sunken Garden.
The green space, which sits opposite the Sears Administration Building on Arthington Street, was designed as a place where workers employed on the 40-acre campus could grab some fresh air, surrounded by lush landscaping, fountains, a reflecting pool and a picturesque pergola.
Long after Sears pulled up stakes, the garden remained a point of neighborhood pride, providing a backdrop for countless special occasions and celebrations. Today, the 1.7-acre jewel is need of some TLC. For the past several years, a coalition of community members and landscape and architecture experts has been marshaling resources to breathe new life into the garden.
In a major coup, they attracted the interest of renowned Dutch garden designer Piet Oudolf, the creative force behind Chicago's Lurie Garden and Manhattan's innovative High Line. Oudolf has developed a planting scheme in his “new perennial” style — favoring plants with year-long interest versus annuals that are pulled up seasonally — a vision that will bring the 100-year-old garden into the modern era.
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Back in the Day: October 23, 2005 - White Sox’s Scott Podsednik Hits Walk-Off World Series Home Run
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Twenty years ago, the Chicago White Sox were in the World Series. The Southsiders were up 1-0 in the series and faced the Houston Astros in Game 2 on a cold and rainy night at what was then called U.S. Cellular Field. The match was a thriller, with both teams trading runs until the 9th inning, where the Astros had tied the game 6-6. In the bottom of the ninth, every White Sox batter had reached base except for Scott Podsednik. Facing the Astros’ All-Star closer, Brad Lidge, Podsednik hammered a pitch delivered right in the middle of the plate over the center-left field wall. It was a walk-off home run and though Podsednik had gone the entire regular season without hitting a home run, his World Series blast was his second of the 2005 postseason. And for those curious, this was not the game that Robert Prevost, also known as Pope Leo XIV, attended. That was Game 1 of the 2005 World Series, which occurred 20 years ago yesterday. |
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This Week’s Arts and Culture Events
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Every Thursday, WTTW News newsletter producer Josh Terry highlights his picks for the week’s must-see cultural events.
Josh Terry: Even though it’s finally starting to feel like fall with the crisp air, leaves fully changing, and weather requiring a light jacket, don’t retreat into hermit mode just yet. There are still several culturally enriching Chicago events to explore. From a hilarious, entertaining and fun showcase of local musical talent covering classic country tunes, an exhibit that celebrates the city’s Latino culture, a neighborhood market highlighting alternative artists and more, check out these arts picks below.
Variety Show: Cosmic Country Showcase — Judson and Moore
The Cosmic Country showcase has been one of the city’s best variety shows, highlighting under-the-radar talent in its thriving music and comedy communities. The long-running event will have a Halloween-themed edition hosted by crooner Andrew Sa and comedian Mary Williamson, alongside performances by Nashville’s India Ramey, Lydia Cash, Dandy Freling, Ric Salazar and more. Tickets for the Saturday night show can be found here.
Art: Aquí en Chicago — Chicago History Museum
As a press release states, "In 2019, students from the Instituto Justice and Leadership Academy in Pilsen protested the Chicago History Museum for its lack of Latino/a/e representation." Now, these students have their own exhibit opening Saturday afternoon. "Through art, photographs, interviews, clothing, personal items, everyday objects, and historical treasures, Aquí en Chicago traces the lives of Latino/a/e communities that have maintained a persistent cultural presence and flourished in Chicago and the surrounding suburbs." Details and tickets can be found here.
Film: Chicago International Film Festival — Multiple Venues
As WTTW News reporter Eunice Alpasan wrote, “The 61st edition of the festival runs Oct. 15-26 at various venues. Screenings will be held at the festival’s hub theater at AMC NEWCITY 14, along with the Music Box Theatre, Gene Siskel Film Center, Chicago History Museum, Logan Center for the Arts at the University of Chicago and more. This year’s festival features 111 feature films and 70 shorts, showcasing cinema from over 60 countries.” You can peruse the full schedule here, but this newsletter producer recommends Hong Sangsoo’s “What Does That Nature Say to You,” Christian Petzold's "Miroirs No. 3," Clint Bentley's "Train Dreams" and Joachim Trier's "Sentimental Value."
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What's your favorite gameday meal in Chicago for watching the Bears? |
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Email DailyChicagoan@wttw.com with your responses and your answers might be published. |
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5:30 PM | 10:00 PM |
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Want more WTTW News content? Follow WTTW on Instagram to check in with us daily, go behind-the-scenes, and more. |
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Newsletter Producer: Josh Terry |
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