Good morning, Chicago. ✶
🔎 Below: Clout-heavy lawyer Allison S. Davis has cost Chicago millions, thanks to a risky real estate venture and unpaid bills, fees and fines. That hasn’t stopped City Hall from doing business with him. Why?
🗞️ Plus: The CTA promises more cops, the Trump administration cuts a grant for support services at many Illinois schools and more.
📝 Keeping score: The Blackhawks’ skid continued with a 4-1 loss to the Canadiens, 4-1.
🧩 New puzzle: We’ve got a new mini crossword — and clue — for you to try below.
📧 Subscribe: Get this newsletter delivered to your inbox weekday mornings.
⏱️: A 9-minute read
TODAY’S WEATHER 🌤️
Partly sunny with a high near 23 and wind chill values as low as -6.
TODAY’S TOP STORY 🔎
Why does City Hall keep doing business with Obama’s old boss who’s cost Chicago millions?
By Tim Novak
Major losses: As a result of deals set in motion nearly two decades ago, five pension plans for Chicago city employers ended up losing more than $54 million on a risky real estate venture run by Allison S. Davis and his business partner, Robert G. Vanecko, a nephew of Mayor Richard M. Daley.
More owed: Today, Davis owes taxpayers $6 million for a mortgage Daley handed him to build senior apartments. Davis also owes City Hall more than $40,000 in unpaid water bills for the apartment complex and more than $360,000 in fees and fines related to those apartments and other projects, according to Mayor Brandon Johnson’s Finance Department.
Debt be damned: These losses aren’t stopping the Johnson administration from continuing to do business with Davis, 85, a retired lawyer who headed Davis Miner Barnhill & Galland PC, the firm that hired President Barack Obama when he was fresh out of law school.
The plans: The Department of Planning and Development agreed to sell two vacant lots to Davis, who wants to build a 26-story hotel a few blocks south of the Obama Presidential Center, hoping to cash in on tourists when it opens next year. Davis’ proposal has won the backing of the Chicago Plan Commission and Ald. Desmon Yancy (5th), whose ward includes the property.
Yancy rethinks?: Asked why City Hall is still doing business with Davis, given his track record, Yancy said he wouldn’t have given his support if he had known about all of the money Davis owes and has cost City Hall.
TRANSPORTATION 🚆
Under CTA ‘security surge plan,’ more police will be on trains, platforms, buses
By David Struett
Patrols promised: More Chicago police officers will patrol CTA trains, platforms and buses under a “security surge plan” developed by both of the agencies. The Chicago Transit Authority announced the program will begin Friday, the same day the Federal Transit Administration demanded the agency implement a security plan or face a clawback of federal funding.
How it will work: Under the plan, the Chicago Police Department will increase the number of cops patrolling the CTA in its Voluntary Special Employment Program from an average of 77 officers per day to 120, the CTA said. Under the program, officers sign up to patrol the CTA on their days off. Private security canine staffing will also increase from an average of 172 canine guards per day to 188.
Budget OKd: In other transit news, the Regional Transportation Authority on Thursday approved the 2026 budgets for the CTA, Metra and Pace, keeping fares the same in one of its last big acts before the newly signed transit law eliminates the body.
EDUCATION 📚
- Cutting support: The Trump administration told ACT Now Illinois last week that it is discontinuing the Community Schools grant effective Dec. 31. The organization was supposed to receive $18 million in 2026 and another $37 million in the following two years. Student support services that will be impacted include mental health programs and food pantries.
- Instituto sanctioned: State officials gave Instituto Health Sciences Career Academy school the harshest possible sanction after an investigation found three years of “repeated and unresolved” special education violations.
- Closed schools get sold: The Chicago Board of Education on Thursday approved the sales of three former school buildings to buyers — including Dionne Mhoone, mother of slain Chicago Police Officer Aréanah Preston — hoping to turn the sites into housing and a community center. But it could be years before those projects get off the ground.
MORE NEWS YOU NEED 🗞️
- Work van burglary: Three people were arrested Wednesday after a work van burglary in Lake View led to a police chase that saw the getaway vehicle plow into a West Lawn building. The van’s owner, Gerardo Lopez-Moreno, says it’s not the first time his vehicle has been burglarized.
- Jail alternative: The Cook County state’s attorney’s office will launch a new pilot program offering an alternative to jail for teen boys who’ve been accused of serious crimes, emphasizing academic and after-school support services.
- City Hall budget battle: Mayor Johnson said Thursday he would do whatever it takes to avert a government shutdown, which the city faces if City Hall doesn’t pass a 2026 budget by Dec. 30.
- Remembering Matt Siemer: As the head of Mobile Care Chicago, Mr. Siemer expanded the reach of the nonprofit, which provides free health care in underserved communities. He died Dec. 13 at age 43.
- Cannabis reclassified: Cannabis industry leaders in Chicago commended President Donald Trump for signing an executive order Thursday that could reclassify cannabis as a less dangerous drug and create a path for further medical research.
IMMIGRATION ✶
- Photo review: Raids, protests, shootings, arrests, the use of tear gas — Sun-Times photojournalists captured these moments in hundreds of photos over the last several months. See their work here.
- Probe sought: U.S. Sens. Dick Durbin and Tammy Duckworth submitted a criminal referral to the U.S. Department of Justice over alleged constitutional violations, including warrantless arrests and use of excessive force, by federal immigration agents during Operation Midway Blitz.
- Illinois Accountability Commission: A newly formed panel of local officials took its first crack Thursday at trying to hold federal immigration agents accountable for the deluge of alleged abuses across the Chicago area under the Trump administration’s aggressive deportation campaign.
- Proposal rejected: A Village of Broadview committee voted against an attempt to advance an ordinance that would restrict U.S. Immigration and Customs Enforcement from expanding their property under certain criteria.
WEEKEND PLANS 🎉
🛍️ Renegade Craft Fair
5-8 p.m. Friday; 11 a.m.-5 p.m. Saturday and Sunday
📍Morgan Manufacturing, 401 N. Morgan St.
The annual fair returns with more than 170 curated artists hocking jewelry, ceramics, clothing and more.
Admission: $5 suggested
🎄 Millennium Park Holiday Sing-Along
6-7 p.m. Friday
📍 Cloud Gate, 21 E. Randolph St.
Grab a provided songbook and join fellow Chicagoans and visitors near the Bean to sing some merry tunes.
Admission: Free
👟 Winter Walk and Bonfire
9 a.m.-11 a.m. Saturday
📍 Big Marsh Park, 11559 S. Stony Island Ave.
Join Chicago Park District staff for a guided walk through Big Marsh Park’s landscape, followed by hot cocoa around a fire.
Admission: Free
♥️ Pre-Kwanzaa Holiday Celebration & Marketplace
11 a.m.-8 p.m. Saturday
📍Washington Park Refectory, 5531 S. Russell Drive
A celebration of unity, family and heritage with crafts, food, music and storytelling.
Admission: Free
🎶 Noche Buena Alternativa
8 p.m. Saturday
📍 Color Club, 4146 N. Elston Ave.
Local indie band Iniquitous headlines this “holiday party by Mexican Americans for everyone.”
Admission: $18
FROM THE PRESS BOX 🏈🏀
- Stadium stalemate?: State lawmakers have rolled their eyes for years at the Bears’ overtures for help building a new stadium, but the team’s threat to consider moving to Indiana has widened the fault line in a fraying relationship with Illinois’ top Democratic power brokers.
- Bulls analysis: The team needs to put more focus on Matas Buzelis becoming a star player, writes Joe Cowley.
- Defining offseason: As she rehabs an ankle injury, Sky point guard Hailey Van Lith is competing to secure her future in Chicago.
- High school football: The Sun-Times’ Michael O’Brien has made his picks for the best players in this year’s All-Area high school football team.
CHICAGO MINI CROSSWORD 🌭
Today’s clue: 5A: One of two outside the Art Institute
BRIGHT ONE 🔆
A parranda pop-up takes inspiration from Puerto Rican Christmas traditions — and Bad Bunny
By Ambar Colón
Open the door to Le Lo Lai Gallery, and you’ll walk into a world meticulously decorated for Christmastime. There are woodwork touches of Puerto Rican heritage, including a replica of the casita, or small house, that Bad Bunny featured on stage during his Puerto Rican residency this past year.
Through early January, Lasting Memories Events has transformed the new gallery at 2716 W. Division St. into La Parranda Boricua Pop-Up.
A parranda is a Puerto Rican tradition in which families and friends gather to sing aguinaldos — similar to Christmas carols — on foot around the neighborhood. In Chicago winters, many brave souls still travel on foot, while others charter party buses.
Each week, La Parranda Boricua hosts various community organizations and local vendors for salsa, bachata, bomba and cumbia workshops; coquito-making classes; toy drives; and nighttime fiestas.
Organizers Liana Lorenzo and Maria Sánchez hosted a parranda pop-up last year that was so popular that they decided to bring it back and extend it to six weeks.
This year, they began “finding ways to incorporate community and anybody that wants to be part of it,” Lorenzo said.
YOUR DAILY QUESTION ☕️
Yesterday, we asked you: How do you feel about the Bears looking past Arlington Heights for possible stadium sites, including in Northwest Indiana?
Here’s some of what you said…
“A move outside Chicago will cause tremendous financial harm to [the] city’s hotels, restaurants, shops and … tax revenues. If [the] Bears move even inches outside the city, Chicagoans should boycott the team.” — Manisha Makwana
“The site they’re looking at is 24 miles from Soldier Field. Arlington Heights is 30 miles away. What’s exciting is you can still build lakefront and Chicago skyline views in Northwest Indiana.” — Michael Vicari
“Call the Bears bluff! Say, ‘Go ahead and move!’ They will stick with Arlington Heights.” — Robert Haugland
“Gary Bears! … It’s been a long time coming. I could see them at Calumet Park as well. Big beautiful lakefront property — plenty of space right of the Skyway.” — R. Larios
“Let the Bears owners do what they want. It is their team. Don’t ask for our tax dollars to keep money in your pocket.” — Lawrence Rogers Jr.
“Somehow, the Hammond Bears or the Munster Bears doesn’t quite have the same ring to it.” — Davin Loh
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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