It’s Wednesday. Get through the rain with these stories from WTTW News.
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Gail Montenegro appears on “Chicago Tonight” on June 16, 2026. (WTTW News)
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President Donald Trump signed a $70 billion Republican-backed funding bill for immigration enforcement last week and the move comes as many Chicago communities are still dealing with the fallout from “Operation Midway Blitz” and ongoing immigration enforcement efforts. And Democrats have raised concerns that the long-term funding takes away Congress’ oversight power.
Gail Montenegro, a former spokesperson for the INS and ICE and a former public affairs officer with the Executive Office for Immigration Review, joined “Chicago Tonight” to share her thoughts on the current state of immigration enforcement in the U.S.
In her roles with the INS, ICE and immigration courts, Montenegro conducted ridealongs with reporters as a bridge between the public and immigration enforcement officers.
She frequently worked alongside ICE agents in processing media inquiries about specific situations, describing her relationship with the agents as cordial and friendly.
What stood out to her at the time was the amount of training required for agents, including strict guidelines dedicated to judicial warrants and criminal prosecution.
Shortly after starting her role with the immigration courts, Montenegro said she worked with local organizations to coordinate schedules for court sit-ins on behalf of organizers and community stakeholders. But she said community outreach all but ended during Trump’s first term.
Montenegro accepted an early retirement offer from the Trump administration in 2025. Since then, her concerns over the agencies she represented have risen significantly.
On ‘Operation Midway Blitz’ and the state of immigration enforcement:
“It actually took place in my own neighborhood in the northern suburbs. We saw it firsthand. It was unlike anything I had ever seen, and this was an agency that I had represented and spoken on behalf of for 15 years.”
On detention centers and prisons in foreign countries:
“The removal process is a civil legal process. It’s not punitive in nature, it’s not a criminal proceeding. So to remove individuals to a third country and to put them in prison there, I just don’t understand what they’re in prison for. They have not committed a crime there. They should not be serving a criminal sentence in another country’s prison. So that is very concerning to me."
On repairing public trust:
“I feel like so much damage has been done, and this is an agency that really had to fight for its place...But I am really saddened to see what has become of ICE’s reputation, and it’s going to be very difficult to repair it. I hope it’s possible at all.”
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Former Ald. George Cardenas kicked off his mayoral campaign in a June 16, 2026, speech. (WTTW News)
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Longtime 12th Ward Ald. George Cardenas is the latest challenger seeking to unseat Brandon Johnson in next year’s mayoral election.
The former alderperson and current Cook County Board of Review commissioner kicked off his campaign during a lunch event on Chicago’s Southwest Side Tuesday at which he pledged to tackle the city’s fiscal and public safety issues.
“Chicago does not need magical thinking,” he told supporters at New Star Lighting, “it needs serious management.”
Cardenas becomes the second candidate to launch their campaign this month, joining state Comptroller Susana Mendoza who announced her own plans to run June 3. Also running are U.S. Rep. Mike Quigley and businessmen Joe Holberg and Liam Stanton, while others including Cook County Treasurer Maria Pappas and Illinois Secretary of State Alexi Giannoulias are expected to enter the race.
Some backstory:
Cardenas represented McKinley Park and parts of Little Village and Brighton Park during his tenure as 12th Ward alderperson, which lasted from 2003 until his resignation in November 2022 following his election to the Cook County Board of Review, a position he still holds.
During his time on the City Council, Cardenas chaired its Committee on Environmental Protection and Energy and served as an ally to former Mayors Richard M. Daley, Rahm Emanuel and Lori Lightfoot.
He acted as Lightfoot’s deputy floor leader at the time of his resignation.
Cardenas centered his remarks Tuesday on fiscal discipline, Tax Incremental Financing reform and public safety improvements, which he said would be priority No. 1 if he is elected.
Cardenas did not specifically call out Johnson during his remarks Tuesday, but he did point to “management” and “governance” problems and said city leaders must make changes as Chicago is owed billions in uncollected debt while asking “more and more” from its taxpayers.
“When city government is disorganized, families pay the price,” he said, “and when fiscal controls are weak, neighborhoods will suffer.”
Chicago’s mayoral election is scheduled for Feb. 23, 2027.
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Piping plovers Blaze and Pepper get reacquainted in Waukegan. Volunteer plover monitors are now on nest watch for the second time this season. (Oliver Slater)
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Piping plover chicks have hatched at Montrose Beach, where parents Imani and Sea Rocket are now keeping close watch over their brood of four as they explore Chicago’s lakefront.
The clutch at Waukegan has also hatched — but in Michigan. The how and why behind that development is a tale full of remarkable plot twists.
“It’s been the gamut of emotions up here,” said Carolyn Lueck, president of Lake County Audubon Society and chair of Sharing Our Shore-Waukegan.
There was heartbreak on the morning of June 12 when monitors saw that the previous night’s severe storms had pushed waves up onto the shoreline where plovers Blaze and Pippin had established a nest. The pair’s four eggs had washed away.
“Our hearts sank,” Lueck said.
Volunteers scoured the beach and miraculously all four eggs were ultimately recovered, intact, from a channel further up the shore.
“We went from absolute despair to a little hope,” Lueck said, knowing that the eggs’ lengthy exposure to the elements stacked the odds against the chicks hatching.
And yet hatch they did. After being taken to Lincoln Park Zoo for stabilization, the eggs were retrieved by a team from the Detroit Zoo, which is a partner in the piping plover recovery effort, and all four chicks successfully hatched.
What’s next:
The chicks will be cared for at the University of Michigan Biological Station in northern Michigan, where they will become part of the same captive-rearing program that produced Blaze and Sea Rocket.
That doesn’t mean monitoring season is over for volunteers in Waukegan. In fact, it might just be getting started. Again. It seems Blaze has renewed her relationship with Pepper, her mate in 2024 and 2025.
“Blaze and Pepper have been mating non-stop since Saturday,” said Lueck. “We could have a second clutch.”
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More From WTTW News:
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Back in the Day: June 17, 2021 - Bears Officially Submit Bid to Purchase Arlington Heights Racetrack
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The drama surrounding a new stadium for the Chicago Bears has generated headlines throughout this decade, but the NFL team’s quest for a new permanent home goes back more than 50 years. When the Bears moved to Soldier Field in 1971, they envisioned it as a temporary stopgap and even threatened a relocation to Arlington Heights in 1975. (Mayor Richard J. Daley responded by saying he would sue the franchise to remove Chicago from its name.) But five years ago today, the Bears reignited the debate by submitting a bid to buy a 326-acre parcel of land from Churchill Downs Inc that was a former horse racing track. Then-Mayor Lori Lightfoot decried the move, saying it was “clearly a
negotiating tactic that the Bears have used” before, adding, “And like most Bears fans, we want the organization to focus on putting a winning team on the field, beating the Packers finally and being relevant past October.”
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Chicago-Area Live Music Recommendations for June 17-23
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Each Wednesday, WTTW News producer Josh Terry presents must-see live music shows from indie rock to jazz, country, hip-hop and more.
Wednesday, June 17:
Memory Card, imy3, The Philadelphia Eagles, Cambodian SIM Card at Empty Bottle. Tickets.
The headliner is one of Chicago’s most exciting indie rock bands.
The Strokes, Thundercat, Hamilton Leithauser at United Center. Tickets.
An eclectic lineup of beloved artists plays an arena show.
Thursday, June 18:
The Hotelier, Graham Hunt at Lincoln Hall. Tickets.
The emo band celebrates 10 years of their album “Goodness” in Lincoln Park.
Mikaela Davis at SPACE. Tickets.
The jam band-adjacent harpist mines just as much from Sheryl Crow as the Grateful Dead on her latest album.
Friday, June 19:
Trombone Shorty & Orleans Avenue, Grace Potter, Jonah Kagen, Lily Fitts, Lucero, Mo Lowda and The Humble, more at Winnetka Music Festival. Tickets.
This North Shore music festival has become a destination for folk, Americana and more.
The Hoyle Brothers at Empty Bottle. Free.
Want a matinee show? This honky tonk residency is always on Fridays at 5:30 p.m. and always free.
Saturday, June 20:
Father John Misty, Petey USA, Ben Kweller, Futurebirds, Jonah Kagen, Lauren Watkins, Bayonne, V.V. Lightbody, more at Winnetka Music Festival. Tickets.
This North Shore music festival has become a destination for folk, Americana and more.
Greg Mendez, Scarlet Rae at Lincoln Hall. Tickets.
This Philadelphia songwriter’s songs are lucid, vulnerable and stunning.
Rosalía at United Center. Tickets.
The Spanish pop star makes another arena stop in the city.
Prewn, Pearl Sugar at Schubas. Sold out.
This incredibly talented cellist and indie rocker has Illinois roots.
Monday, June 22:
Shelia E., Melody Angel at Millennium Park. Free.
A chance to see an adventurous pop music legend for free downtown.
Tuesday, June 23:
Hazel City, Maxwell Blast at Sleeping Village. Tickets.
Fresh off nine consecutive sold-out nights at Thalia Hall, the Twin Peaks guitarist plays a solo show in Avondale.
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What's your favorite beach in Chicago? Tell us why.
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Email DailyChicagoan@wttw.com with your responses and your answers might be published.
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5:30 PM | 10:00 PM
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Newsletter Producer: Josh Terry
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