Trump taps City Hall contractors for ICE operation

Good morning, Chicago. ✶

🔎 Below: A Sun-Times investigation found overlapping vendors who have served both City Hall and the federal government in its campaign against immigration in the Chicago area.

🗞️ Plus: A jury found an ex-cop guilty of second-degree murder for fatally shooting Sonya Massey; nearly 2 million Illinois residents, and local food banks, brace for Saturday’s SNAP cutoff; and more news you need to know.

📝 Keeping scoreThe Bulls beat the Kings, 126-113.

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⏱️: An 8-minute read


TODAY’S WEATHER 🌤️

Mostly sunny with a high near 57. 


TODAY’S TOP STORIES

Mayor Brandon Johnson speaks to thousands of protesters gathered in Grant Park at the “No Kings” protest downtown, Saturday, Oct. 18, 2025. | Candace Dane Chambers/Sun-Times.

Mayor Brandon Johnson speaks to thousands of protesters gathered in Grant Park at the Oct. 18 “No Kings” protest.

Candace Dane Chambers/Sun-Times

Trump taps big City Hall contractors for ICE operation that Mayor Johnson opposes

By Tom Schuba

Contractors straddle sides: Chicago-area companies that earned lucrative contracts supporting President Donald Trump’s deportation push also benefited from deals with the city, the Sun-Times found. A Sun-Times review of public procurement databases for city and federal contracts reveals overlapping vendors who’ve served both City Hall and the federal government.

Overlapping needs: A web of agreements shows Trump’s regime and the administration of Mayor Brandon Johnson have overlapping needs — even as they spar publicly and agree on next to nothing. 

Council call: Ald. Rossana Rodriguez (33rd) is calling for a city review to determine whether Chicago taxpayer dollars should be going to firms working with the U.S. Department of Homeland Security and its on-the-ground agencies, Immigration and Customs Enforcement and Customs and Border Protection.

Deals’ details: The deals are among millions of dollars in contracts granted to Illinois firms supporting federal immigration enforcement agencies, including relocation services for agents and the sale of pepper balls that agents routinely use to fire on protesters.

READ MORE

✶✶✶✶

Donna Massey, mother of Sonya Massey, wipes tears from her face as she listens to Rev. Al Sharpton speak during a July 30 news conference at New Mount Pilgrim Church.

Donna Massey, mother of Sonya Massey, wipes tears as the Rev. Al Sharpton speaks in July 2024.

Tyler Pasciak LaRiviere/Sun-Times file

Jury finds ex-cop guilty of second-degree murder for fatally shooting Sonya Massey

By Mawa Iqbal

The verdict: A downstate jury convicted a white ex-cop of second-degree murder Wednesday for fatally shooting Sonya Massey in a verdict that bitterly disappointed family members of the slain, unarmed Black woman. Former Sangamon County Sheriff’s Deputy Sean Grayson was found guilty of one count for killing Massey in her Springfield-area home last year. Prosecutors had sought convictions on three counts of first-degree murder.

Key context: The fatal encounter between Grayson and Massey spurred changes in state policing laws and led to a $10 million settlement to her family from Sangamon County. But it was the 36-minute police video showing her grisly killing that put Massey’s death and the trial in the nation’s conscience.

Possible sentence: That Grayson now won’t face the possibility of life in prison for his conviction on the lesser murder charge upset the 36-year-old mother’s family. The second-degree murder conviction means Grayson could face four to 20 years behind bars. Sentencing is set for Jan. 29.

READ MORE

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From left, Aubrey Lewandowski of Palos Hills and Natasha McClendon of Englewood.

From left, Aubrey Lewandowski of Palos Hills and Natasha McClendon of Englewood.

Pat Nabong/Sun-Times, Nima Taradji/For the Sun-Times

These Illinois moms are among millions facing SNAP cutoff

By Elvia Malagón and Casey He

SNAP woes: Nearly 2 million Illinois residents who rely on the Supplemental Nutrition Assistance Program will likely have to find another way to buy food or go without as the federal government shutdown stretches into its fourth week. The SNAP funding cutoff will begin Nov. 1 unless Congress or the White House takes action.

Englewood angle: Natasha McClendon told the Sun-Times that in order to feed her two school-age daughters and disabled husband, she will have to take from the family’s savings if the SNAP benefits they’re due don’t materialize. McClendon, 49, who works as a substitute teacher assistant for Chicago Public Schools, has been saving to buy their first home.

Palos Hills POV: Aubrey Lewandowski, 41, says she’s scrambling, knowing the SNAP benefits she relies on to help feed her four young children — two of whom have special needs — won’t be coming in November. She works as a delivery driver and anticipates having to spend more time away from her family to pick up additional orders through DoorDash, Instacart and other apps.

READ MORE


RESOURCE GUIDE 🍎

A volunteer stocks shelves at the Nourishing Hope food pantry in Chicago’s Lake View neighborhood.

A volunteer stocks shelves at the Nourishing Hope food pantry in Chicago’s Lake View neighborhood.

Victor Hilitski/For the Sun-Times

Where to find Chicago-area food pantries if SNAP goes away during shutdown

By Elvia Malagón, Casey He and Kristen Schorsch

Executive order: Gov. J.B. Pritzker on Thursday signed an executive order directing $20 million in state funding to support food banks across Illinois starting Saturday. But the state and the food pantries say they can’t match the $350 million that SNAP provides each month.

Finding food: Food pantries across the Chicago area are working to find the food, funds and volunteers needed to support an expected strain on resources as Saturday nears. We’ve compiled a list of area pantries serving residents, regardless of immigration status.👇

FULL LIST HERE


IMMIGRATION ✶

Sarai and Arnoldo Carrillo say their parents and little brother remain in federal custody after immigration agents raided their Indiana home last week.

Sarai and Arnoldo Carrillo say their parents and little brother remain in federal custody after immigration agents raided their Indiana home last week.

Sun-Times

  • Shaken after raid: Six federal agents forced their way into a family’s home in Gary, Indiana, last week. They took the entire family into custody: Arnoldo Carrillo Jr.; his father, Rosario; his mother, Martha; his sister, Sarai; and his 14-year-old brother. Arnoldo and Sarai were both released. The parents and their teen son are still in custody.
  • Meetings called off: The federal appeals court in Chicago put a temporary hold until Nov. 5 on U.S. District Judge Sara Ellis’ requirement that Border Patrol boss Gregory Bovino appear in her courtroom every weeknight.
  • Political candidates charged: Federal prosecutors in Chicago drew swift criticism Wednesday with the unsealing of a grand jury indictment that charges six people, including congressional candidate Kat Abughazaleh, with conspiring to impede a federal officer in Broadview.
  • Guard on hold: President Trump’s deployment of National Guard troops within Illinois will likely remain on hold through mid-November after the U.S. Supreme Court sought more information from lawyers Wednesday.
  • Halloween request: Gov. Pritzker asked U.S. Homeland Security Secretary Kristi Noem and top ICE officials to suspend immigration enforcement operations throughout Chicago for three days so children can safely celebrate Halloween. The request comes four days after ICE agents fired tear gas in Old Irving Park as costumed children walked to a parade.

MORE NEWS YOU NEED 🗞️

Gov. JB Pritzker speaks during a news conference in the Loop on Oct. 23.

Gov. JB Pritzker said a transit funding bill needed “a lot of work” days before the state legislature adjourns.

Ashlee Rezin/Sun-Times

  • Pumping the brakes: Gov. Pritzker is opposing Illinois House Democrats’ transit funding proposal as the legislative clock winds down for state lawmakers to agree on new taxes to help the CTA, Metra and Pace avert a fiscal crisis. The plan that includes taxes on streaming services and sporting event tickets is “not going forward” as is, he said.
  • Johnson’s job rating: Mayor Johnson’s job approval rating has inched up to 31%, but Chicagoans are less enthusiastic about his $600 million tax plan to “challenge the ultra-rich and corporations to pay their fair share,” a new poll shows.
  • Pension reimbursement: The Chicago Board of Education will be asked to approve a contract to reimburse the city for a $175 million pension payment for nonteaching school employees — only if City Council agrees to declare a $1 billion tax increment-financing surplus to bail out CPS.
  • 1871 finds new home: After leaving Merchandise Mart earlier this year, the tech incubator says it plans to move into an office space near the Loop that was donated by public relations giant Edelman.
  • David Byrne review: The innovative musician brought more than 50 years of showmanship to the Auditorium on Tuesday, kicking off a four-night run and balancing nostalgia with sobering reflections of life in America today.

FROM THE PRESS BOX 🏈🏒🏀

  • Will Williams improve?: Mistakes like last Sunday’s interception against the Ravens are only valuable if Bears QB Caleb Williams grows from them, writes Jason Lieser.
  • So far, so good: With a 5-3-2 record and plus-seven goal differential, the Blackhawks have exceeded expectations, but a six-game road trip will now test the legitimacy of their resurgence.
  • Sister Jean honored: The Loyola men’s basketball team will wear uniform patches honoring their beloved late chaplain Sister Jean Dolores Schmidt.

GAMES AND CROSSWORDS 🧩

GAMES AND PUZZLES

    This week’s Chicago-style crossword theme is: Halloween 🎃

    Here’s your clue: 
    9A: ___-or-Treat (Trick-or-Treat alternative)

    PLAY NOW


    BRIGHT ONE 🔆

    Brown bears Ash and Lexi are now housed at Lincoln Park Zoo, the first time the zoo has had brown bears since 1979.

    Ash and Lexi are now housed at Lincoln Park Zoo, the first time it has had brown bears since 1979.

    Provided

    Lincoln Park Zoo welcomes brown bears for the first time in 46 years

    By Mary Norkol

    Two more bears are ready to make Chicago their home, but this time not at Soldier Field.

    Lincoln Park Zoo welcomed two female brown bears, Ash and Lexi, who debuted Monday after coming to Chicago from Henry Vilas Zoo in Madison, Wisconsin. The bears, who are aunt and niece but commonly mistaken for sisters, are both adults, though their exact ages are unknown.

    The bears are very close and playful with one another, Henry Vilas Zoo employees told the Lincoln Park Zoo. Ash is quicker to participate in training sessions, as she is more food motivated, but Lexi has been called the braver of the two and is more eager to try new things.

    Ash and Lexi are the first brown bears at Lincoln Park Zoo since 1979.

    READ MORE


    YOUR DAILY QUESTION ☕️

    What is your defining memory of Halloween growing up in Chicago?

    Email us (please include your first and last name). We may include your answers in Friday’s Morning Edition newsletter.


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    Written and curated by: Matt Moore
    Editor: Eydie Cubarrubia


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