Daywatch: Troubled Cook County tech firm used insider lobbyist

Good morning, Chicago.

As a fledgling tech contractor looking to build its business in the insular world of Cook County politics, Texas-based Tyler Technologies turned to one of Illinois’ most well-connected lobbyists to get the job done.

In 2016, Jay Doherty not only lobbied Chicago, Cook County and state agencies, he was also the longtime president of the City Club of Chicago, a popular nonprofit civic organization.

Doherty would be convicted in 2023 of conspiracy in a scandal involving one of his other clients, Commonwealth Edison. It was part of a series of linked cases that ultimately ended Madigan’s decades-long run as speaker.

There is no direct connection between Doherty’s work for ComEd and what he did for Tyler. Unlike Tyler’s efforts seeking contract opportunities, the ComEd case detailed a vast criminal scheme of bribery and influence peddling as part of the utility’s efforts to get legislation passed.

But interviews and records about Doherty’s work for Tyler and details from his 2023 trial reveal striking parallels in how he repeatedly smoothed paths for both clients, including creating informal interactions at City Club events attended by government officials so the two sides could discuss business outside the office.

Read the latest in our reporting on the troubled tech firm, from the Tribune’s A.D. Quig and David Jackson of Injustice Watch.

Here are the top stories you need to know to start your day, including: why an alderman wants to give the City Council power to ban short-term rentals, the cost-cutting measures Northwestern University is implementing and our summer books guide.

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Protesters gather to denounce U.S Immigration and Customs Enforcement operations on June 10, 2025, in Los Angeles. (AP Photo/Damian Dovarganes)

LA police enforce downtown curfew as protests continue against President Donald Trump’s immigration crackdown

Los Angeles police swiftly enforced a downtown curfew last night, making arrests moments after it took effect, while deploying officers on horseback and using crowd control projectiles to break up a group of hundreds demonstrating against President Donald Trump’s immigration crackdown.

Members of the National Guard stood watch behind plastic shields, but did not appear to participate in the arrests.

Demonstrators gather across from the Centers for Disease Control and Prevention headquarters during a staff walkout to protest the dismantling of the Advisory Committee on Immunization Practices in Atlanta on June 10, 2025. Robert F. Kennedy Jr., the health secretary, on Monday fired all 17 members of the advisory committee, saying the move would restore the public's trust in vaccines. (Melissa Golden/The New York Times)
Demonstrators gather across from the Centers for Disease Control and Prevention headquarters during a staff walkout to protest the dismantling of the Advisory Committee on Immunization Practices in Atlanta on June 10, 2025. Robert F. Kennedy Jr., the health secretary, on Monday fired all 17 members of the advisory committee, saying the move would restore the public’s trust in vaccines. (Melissa Golden/The New York Times)

Chicago-based American Medical Association to ask Senate to investigate RFK Jr.’s firing of vaccine committee members

The Chicago-based American Medical Association plans to ask a U.S. Senate committee to investigate Robert F. Kennedy Jr.’s decision to overhaul a key vaccine advisory group, the medical association said in an emergency resolution.

Agricultural workers in the U.S. on H-2A visas place wooden stakes in the ground for jalapeno plants at Flamm Orchards, May 29, 2025, in downstate Cobden. At peak season in June and July, Flamm Orchards employs about 90 workers from Oaxaca, Mexico. (Armando L. Sanchez/Chicago Tribune)
Agricultural workers in the U.S. on H-2A visas place wooden stakes in the ground for jalapeno plants at Flamm Orchards, May 29, 2025, in downstate Cobden. At peak season in June and July, Flamm Orchards employs about 90 workers from Oaxaca, Mexico. (Armando L. Sanchez/Chicago Tribune)

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Senate President Don Harmon looks over the paperwork of a House bill during debates on the Senate floor at the Illinois Capitol building on May 29, 2025, in Springfield. (John J. Kim/Chicago Tribune)
Senate President Don Harmon looks over the paperwork of a House bill during debates on the Senate floor at the Illinois Capitol building on May 29, 2025, in Springfield. (John J. Kim/Chicago Tribune)

Illinois Senate President Don Harmon faces potential $9.8 million fine for improperly accepting campaign cash

State election officials have informed Senate President Don Harmon that he will face more than $9.8 million in penalties pending an appeal of a case alleging he broke an Illinois election law designed to rein in big money in political campaigns.

Former Speaker Michael Madigan, second from left, waits to cross Jackson Boulevard with attorney Thomas Breen as they arrive at the Dirksen U.S. Courthouse for a hearing on sentencing guidelines on June 10, 2025. (Antonio Perez/Chicago Tribune)
Former Speaker Michael Madigan, second from left, waits to cross Jackson Boulevard with attorney Thomas Breen as they arrive at the Dirksen U.S. Courthouse for a hearing on sentencing guidelines on June 10, 2025. (Antonio Perez/Chicago Tribune)

Judge strikes reference to Madigan’s personal fortune of more than $40 million from sentencing record

A federal judge yesterday struck from the court record a reference to former Democratic House Speaker Michael Madigan’s personal net worth of more than $40 million, agreeing with his defense team that it should have been kept private.

Federal prosecutors made Madigan’s net worth public for the first time in a response to a sentencing memorandum filed by his attorneys, arguing that the defendant’s “greed is even more appalling given his law firm’s success.”

Ald. Anthony Napolitano, 41st, speaks at City Hall on Feb. 4, 2025. (Eileen T. Meslar/Chicago Tribune)
Ald. Anthony Napolitano, 41st, speaks at City Hall on Feb. 4, 2025. (Eileen T. Meslar/Chicago Tribune)

Alderman seeks power to ban short-term rentals from Chicago precincts

If a Far Northwest Side alderman gets his way, Chicago City Council members could gain the authority to block short-term rentals like Airbnb’s from popping up in their wards.

A bicyclist passes by the arch on the Northwestern University campus on March 31, 2025, in Evanston. (Brian Cassella/Chicago Tribune)
A bicyclist passes by the arch on the Northwestern University campus on March 31, 2025, in Evanston. (Brian Cassella/Chicago Tribune)

Northwestern announces cost-cutting measures amidst growing financial pressures

In an email to faculty and staff yesterday, Northwestern University announced it would implement several cost-cutting measures, including a hiring freeze and budget cuts, due to rising costs and uncertainty at the federal level.

The university faces serious financial pressure following the Trump administration freezing $790 million in federal funding in April. Northwestern has reached a moment where these measures are necessary to ensure the university’s fiscal stability now and “into an uncertain future,” University leadership said in the email.

Chicago Bears guard Theo Benedet (79) and offensive tackle Ozzy Trapilo (75) participate in a drill during practice at Halas Hall on Tuesday, June 10, 2025. (Eileen T. Meslar/Chicago Tribune)
Chicago Bears guard Theo Benedet (79) and offensive tackle Ozzy Trapilo (75) participate in a drill during practice at Halas Hall on June 10, 2025. (Eileen T. Meslar/Chicago Tribune)

Chicago Bears OTAs: While Ozzy Trapilo battles for left tackle, Colston Loveland and Luther Burden remain sidelined

In a sense, now is the best time to make a position switch. Or, at least, that’s how Bears rookie tackle Ozzy Trapilo is looking at it.

After playing right tackle during his final two seasons at Boston College, Trapilo is making the move to the left side. He played some left tackle in college, but re-learning the position is still a transition.

Nico Parker and Mason Thames in the remake of "How to Train Your Dragon." (Universal Pictures)
Nico Parker and Mason Thames in the remake of "How to Train Your Dragon." (Universal Pictures)

‘How to Train Your Dragon’ review: The live-action remake meets our expectations. Is that enough?

What can one say about the new “How to Train Your Dragon” that one didn’t say back in 2010, when it was animated, not live-actioned? And really good?

One can say that the remake gets the job done, writes Tribune film critic Michael Phillips. One can also say the job is not an inspiring one. Reworking a familiar, proven narrative in an animation-to-“real”-live-action transfer rarely feels, looks and acts like an improvement. But freshness can be irrelevant at the box office for these ventures. (The “Lilo & Stitch” remake is heading toward the billion-dollar global benchmark.)

From left: Nina Singh and Stephen Moyer star in "Art Detectives." (Acorn TV)
From left: Nina Singh and Stephen Moyer star in "Art Detectives." (Acorn TV)

‘Art Detectives’ review: A police procedural focused on art world crimes

Most TV detectives have a gimmick. Just doing the diligent work of piecing together a puzzle isn’t enough. And to a minor extent, that’s true of “Art Detectives” on Acorn TV, about a policeman who heads up the one-man Heritage Crime Unit in the U.K. His specialty is crime linked to the art world, writes Tribune TV and film critic Nina Metz.

Summer reading books top to bottom, "Pan" by Michael Clune, "Clam Down" by Anelise Chen, "King of Ashes" by S.A. Cosby, "Charlottesville" by Deborah Baker, "Spent" by Alison Bechdel, "So Far Gone" by Jess Walter, and "Murder Takes a Vacation" by Laura Lippman. (Stacey Wescott/Chicago Tribune)
Summer reading books top to bottom, “Pan” by Michael Clune, “Clam Down” by Anelise Chen, “King of Ashes” by S.A. Cosby, “Charlottesville” by Deborah Baker, “Spent” by Alison Bechdel, “So Far Gone” by Jess Walter, and “Murder Takes a Vacation” by Laura Lippman. (Stacey Wescott/Chicago Tribune)

Summer books 2025: Get lost in our shelves of Chicago, spiritual or just plain weird books

Summer reading, if you ask me, should meander, without a plan, writes Christopher Borrelli. Pick up, put down, misplace, leave crusty with sand or warped with humidity. Fall is for rigor, winter for hunkering down, spring for peering ahead, but the right summer read is a promising dirt road in a field.

Friends from a local car club along with tourists passing through town mingle outside the Hackberry General Store on Route 66 in Arizona on June 6, 2025. (E. Jason Wambsgans/Chicago Tribune)
Friends from a local car club along with tourists passing through town mingle outside the Hackberry General Store on Route 66 in Arizona on June 6, 2025. (E. Jason Wambsgans/Chicago Tribune)

Route 66: A rainy day at the Hackberry General Store

Located on Route 66 about 30 miles east of Kingman at the edge of the Peacock Mountains in northwest Arizona, the general store was perhaps destined to become another crumbling ruin when the route was decommissioned in 1985.

That is, until Bob Waldmire came to town.

Waldmire’s family opened the Springfield, Illinois, institution Cozy Dog, which is located on Route 66 and claims to have invented the corn dog. Born in St. Louis, he became a legendary figure of the route’s lore with his hand-drawn postcards, maps and murals. Both he and the van he took on his frequent route trips served as the inspiration for the character Fillmore in the Disney Pixar film “Cars.”

Route 66 road trip: 

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