How Trump plans to target Chicago

Good morning, Chicago. ✶

🔎 Below: Troops have been sent to Chicago before — and often made things worse.

🗞️ Plus: How President Donald Trump is planning to target Chicago, who’s eligible for “no tax on tips” and more news you need to know.

📝 Keeping scoreThe Cubs fell to Atlanta, 5-1; the White Sox beat the Twins, 4-3; the Sky bested the Sun, 88-64.

⏱️: A 7-minute read


TODAY’S WEATHER 🌤️

Mostly sunny with a high near 68.


TODAY’S TOP STORIES

A U.S. Customs and Border Protection officer speaks with gthe rounds crew at Gary/Chicago International Airport, Thursday, Aug. 14, 2025, in Gary, IN.

A U.S. Customs and Border Protection officer is spotted at Gary/Chicago International Airport last month.

Tyler Pasciak LaRiviere/Sun-Times

Flash-bang grenades and early morning raids: How Trump is planning to target Chicago

By Violet Miller, Mitchell Armentrout, Cindy Hernandez, Mary Norkol and Emmanuel Camarillo

Troop tactics: Hundreds of federal agents who are being sent to a north suburban naval base this week are expected to leave the facility before dawn each morning to carry out President Trump’s mission to curb crime and make immigration arrests in Chicago, officials have been told.

From the West Coast: The 230 agents, at least some of whom work for U.S. Customs and Border Protection, are coming from Los Angeles, where an immigration blitz this summer spurred protests that pushed Trump to call in the National Guard, sources familiar with the planning said.

Growing presence: At least 30 agents have already arrived at Naval Station Great Lakes near North Chicago, where they’ve been practicing crowd control with shields and flash-bang grenades, the sources said.

Pritzker’s projection: Gov. JB Pritzker says he expects U.S. Immigration and Customs Enforcement agents to be “assembled, ready to go on Friday, and that they will begin actions on Saturday or over the weekend.” The federal agency still hasn’t confirmed any details with Pritzker’s office, which thinks the raids have been timed to coincide with Mexican Independence Day festivities.

People walk near the Little Village Arch on West 26th Street in Little Village amid news of the anticipated deployment of federal troops and potential ICE arrests, Wednesday, Sept. 3, 2025.

In Little Village, the 26th Street Mexican Independence Day Parade is set for Sunday.

Pat Nabong/Sun-Times

Parade precautions: Pilsen’s Mexican Independence Day parade will be held Saturday with additional precautions, including volunteers stationed throughout the route, ready to alert any issues, organizers said. In Little Village, the 26th Street Mexican Independence Day Parade is set for Sunday. El Grito Chicago in Grant Park is scheduled for Sept. 13.

Detained at court: A woman was detained by federal immigration agents Wednesday while arriving at Cook County’s domestic violence courthouse, raising concerns that Trump’s plan to ramp up enforcement has taken hold.

AG weighs in: Illinois Attorney General Kwame Raoul, in a legal brief filed Tuesday, urged a federal court to strike down a U.S. Department of Homeland Security policy denying bond hearings to detained immigrants.

Remote learning calls: As Chicago braces for immigration raids and the possibility of National Guard troops on the streets, the Chicago Teachers Union is urging Chicago Public Schools to be ready to offer online learning options for families who want to keep their children home in fear of being targeted.

READ MORE


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MORE NEWS YOU NEED

Jeremy Herred Sr. stands with his wife at a press conference announcing the filing of a civil lawsuit against the Chicago Park District and former lifeguard Charles Leto who shot their son, 14-year-old Jeremy Herred in June, Wednesday, Sept. 3, 2025.

Jeremy Herred Sr. on Wednesday announced a civil lawsuit against the Chicago Park District and a former lifeguard who allegedly shot his son and another boy.

Candace Dane Chambers/Sun-Times

  • Families sue after shooting: The families of two teens shot at Douglass Park pool are suing a former lifeguard and the Chicago Park District. Charles Leto is accused of fatally shooting 15-year-old Marjay Dotson and wounding 14-year-old Jeremy Herred on June 26.
     
  • Developers wanted: The city is looking for developers to revive more than a dozen vacant lots near the United Center, ahead of the arena’s ownership kicking off construction of its $7 billion 1901 Project.
     
  • ‘No tax on tips’ list: Nearly 70 jobs qualify for the tax break as part of a U.S. Department of the Treasury preliminary list. See if you are eligible.
     
  • Parking 911 pilot: Hoping to free up more police officers to respond to serious crimes, a key City Council committee greenlit the development of a pilot program to assign parking-related 911 calls to the Finance Department rather than the Chicago Police Department.
     
  • New outpatient clinic: The new Northwestern Medicine facility, 4822 S. Cottage Grove Ave. in Bronzeville, offers primary care, oncology and infusion services, pediatrics, cardiology, women’s health, dermatology, and mental health services.  
     
  • Things to do Sept. 4-10: “Ashland Avenue,” Printers Row Lit Fest and Taste of Chicago are among the highlights in the week ahead.

GAMES AND CROSSWORDS 🧩

GAMES AND PUZZLES

    This week’s Chicago-style crossword theme is: Labor Day

    Here’s your clue: 
    36A: “The ___ makes us strong” (labor movement slogan)

    ANSWER NOW


    CHICAGO HISTORY ⏳


    As Chicago braces for troops, remember: Soldiers have been here before and often made things worse

    Column by Neil Steinberg

    Soldiers in our streets: The history of American soldiers in Chicago is checkered.

    Help and harm: In one instance, during the 1919 race riots, soldiers created a buffer between Chicagoans bent on murdering each other because of the color of their skin. In another, the 1894 Pullman Strike, soldiers’ arrival — despite the governor’s objections — sparked days of deadly rioting.

    Dig deeper: Chicago could get a significant new chapter in its history with troops as Trump plans to deploy the National Guard to the city. We took a look at that history, tracing as far back as the early 1800s.

    READ MORE


    FROM THE PRESS BOX 🏀🏈⛳

    • Reese reality check: Angel Reese says she won’t settle for another season like this one — and isn’t sure what will draw free agents to the Sky. It’s the latest turn in her escalating skepticism.
    • Bears schedule: Here’s what you need to know about the Bears’ 2025 schedule, game-by-game, for coach Ben Johnson’s debut season.
    • CHSN Layoffs: Chicago Sports Network let go of several staffers this week, including Bears reporter Alex Shapiro. The network declined to comment.
    • Suburban golf tournament: Palatine native and viral golfer Tom “Bubbie” Broders will host a one-day tournament Thursday at Kemper Lakes Golf Club. Fellow golf influencers will compete to win money for themselves and for charity.

    BRIGHT ONE ✨

    CPS butter cookie test

    Butter cookies based on a recreation of the Chicago Public Schools’ classic recipe sit ready to be baked.

    Justin Bull/WBEZ

    Putting the CPS butter cookie to the test

    Reporting by Erin Allen, Justin Bull and Susie An

    It may come as a surprise, but decades ago, Chicago Public Schools students actually looked forward to eating cafeteria lunch.

    Many CPS alumni remember an old lunchtime staple, the famed CPS butter sugar cookie — served districtwide and baked fresh by lunchroom staff from the 1960s to the 1980s.

    The cookie has long been discontinued in schools, but there’s still a devout following. Dozens of copycat recipes pop up on a simple internet search, and one woman even turned it into a business.

    WBEZ’s Curious City radio show decided to put this cookie to the test.

    With the help of CPS culinary instructor Jeffrey Newman and a dupe recipe, Curious City re-created this classic lunchroom treat.

    Listen up 🎧: Is this recipe worth all the hype? Will current CPS students like it? Or is this merely a dose of childhood nostalgia? Hear more and find the full recipe here.


    YOUR DAILY QUESTION ☕️

    This year marks the 40th anniversary of the 1985 Bears — the iconic, shuffling, Super Bowl-winning team.

    We want to know: What is your enduring memory of that time in Chicago sports history?

    Email us (please include your first and last name). To see the answers to this question, check Friday’s Morning Edition newsletter. 


    Thanks for reading the Sun-Times Morning Edition!
    Got a story you think we missed? Email us here.


    Written and curated by: Matt Moore
    Editor: Eydie Cubarrubia

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