Chicago Looks Back on the Roller-Coaster Events of 2025
- Don DeBat
- Jan 5
- 4 min read
Updated: 1 day ago
By Don DeBat
With the dawn of 2026, many Chicago apartment renters, home buyers and bungalow owners probably are wondering how they survived the crazy roller-coaster- ride of 2025.
Read these 2025 stories recently reported by The Home Front column:
• With property tax bills soaring by an average of 16.7%, there are threats of double-digit apartment rent increases on the horizon for spring of 2026.
• Resale home prices in Lincoln Park skyrocketed 25.9% over the past year, while existing North Side property listings are drying up because worried homeowners are sitting pretty on their bargain 3% and 4% mortgages.
• Home-loan interest rates appear to be frozen in a non-affordable zone above 6.5% for the next two years, according to Federal Reserve Board analysts.
• Then, there’s the wacky City of Chicago transportation planners, who by bowing to the bicycle lobby, have spent $17 million to build dozens of miles of elaborate bike lanes across city neighborhoods.
As a result, the fancy racer lanes remove vital street parking at once thriving “Ma and Pa” local businesses and restaurants from North Park to Brighton Park are going bankrupt.
Chicago’s ICE scenario
It may be more important to look back at one of the strangest, most frightening and mentally confusing scenarios to remember about 2025—the Immigration and Custom Enforcement (ICE)invasion of Chicago.
This historic event, dubbed “Operation Midway Blast,” by the Feds impacted the Windy City and other “immigrant friendly” cities across the nation, and led to President Donald Trump ordering nationwide arrests of 67,800 immigrants during one five-month period.
An investigation by the Washington Post found that since January 20, 2025, when Trump took office, through October 1, 2025 about 36% of ICE detainees had criminal convictions, and 30% had pending charges. However, nearly a quarter committed only minor offenses such as traffic violations.
Nearly half of the 79,000 people ICE arrested and placed in detention nationwide between October 1 and the end of November, did not have pending convictions or pending criminal charges.
Of the more than 3,000 immigrants arrested in Chicago, fewer than 100 had criminal convictions or pending charges.
The Trump Administration is pressing for 3,000 immigration arrests a day, and has set a goal of 1 million deportations in the president’s first year of his second term in office, according to the Washington Post.
The administration deported more than 579,000 people in 2025, according to border-czar Tom Homan. For more efficient “feeder system” processing of illegals, ICE recently revealed a secret plan to hold 80,000 immigrants in seven large, industrial warehouses scattered around the country, mostly in the South, reported a Washington Post investigation.
Each warehouse would hold up to 10,000 immigrants. The large warehouses would be located in Virginia, Texas, Louisiana, Arizona, Georgia and Missouri. Sixteen smaller warehouses would hold up to 1,500 people each.
Land of the free?
Is America really the land of the free, home of the brave? A nation founded on liberty and justice for all?
The dedication on the Statue of Liberty reads:
“Give me your tired, your poor. Your huddled masses yearning to breathe free. The wretched refuse of your teeming shore. Send these, the homeless, tempest-toss to me. I lift my lamp beside the golden door!”
In 1900, those words beckoned to by grandfather, a Bohemian coal miner and farmer, who immigrated with his future wife, through the gates of Ellis Island. They came from a European nation now known as the Czech Republic. He eventually mined coal and farmed 40 acres near Terra Haute, Indiana, and his wife gave birth to 11 children, including my mother.
However, in 2025, it was hard to keep the founding fathers’ Constitutional concepts in mind, as masked ICE agents used poison gas, clubs and automatic weapons to persecute and quell ordinary immigrants in the streets of Chicago.
Newspaper photos of armed ICE agents in military uniforms marching near Trump Tower on the banks of the Chicago River really was a downtown eye-opener in for this veteran writer, who witnessed the 1968 riots in Chicago after the assignation of Martin Luther King.
In 2025, veteran downtown and North Side Chicago real estate brokers said they worried about the impact of armed National Guard troops and bullying ICE agents marching through the streets in front of their property showings.
Meanwhile, Michigan Avenue retail-street crime also added to the chaos with gang bangers smashing boutique-shop windows and grabbing arm loads of Rolex watches and Gucci purses.
“Political and economic uncertainty, along with perceived or actual crime rates also kept home sellers on the sidelines,” observed broker John Irwin of Baird & Warner.
“The turmoil at the national and local levels continues to unfold,” Irwin said.
“This makes it impossible to predict with certainty how our local real estate business will be affected in 2026.”
ICE Protests on TV
TV news reports in autumn of 2025 were filled with images of protests of numerous beatings, gassings, shootings, arrest and physical and psychological harassment of Latinos and other minorities.
One protesting Humboldt Park Alderperson was handcuffed by ICE agents. Journalists also were arrested. To avoid arrest, thousands of mostly innocent immigrants avoided work, and hid in their basements and attics to avoid being snatched off the street corners and out of their homes.
Trump’s final solution?
To this writer, this action was reminiscent of a scene from the movie “The Diary of Ann Frank” in Adolph Hitler’s Nazi Germany in the late-1930s. Nazi SS storm troops burned books, jailed political dissidents, smashed storefront windows of minority businesses during “Crystal Nacht.” Those events eventually led to the elimination of six million Jews as the “Final Solution.”
To his credit, Chicago Police chief Larry Snelling says Windy City cops operate by a different set of rules than federal ICE agents.
“Chicago police training is different than Ice training,” Snelling said on TV. “When working with protesters, we show more restraint. Cops don’t use gas.
Cops don’t wear masks. They wear body cameras. Cops serve and protect the people of Chicago.”
For more softball and housing news, visit www.dondebat.biz. DeBat, inducted into the softball Hall of Fame in 1999, is writing “Chicago’s Game,” a book on 16-inch softball. He is co-author of “Escaping Condo Jail,” the ultimate survival guide for condominium living. Visit www.escapingcondojail.com
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