In Chicago, an immense show of force signals a sharp escalation in White
House immigration crackdown
[October 21, 2025]
By TIM SULLIVAN
CHICAGO (AP) — The music begins low and ominous, with the video showing
searchlights skimming along a Chicago apartment building and heavily
armed immigration agents storming inside. Guns are drawn. Unmarked cars
fill the streets. Agents rappel from a Black Hawk helicopter.
But quickly the soundtrack grows more stirring and the video — edited
into a series of dramatic shots and released by the Department of
Homeland Security days after the Sept. 30 raid — shows agents leading
away shirtless men, their hands zip-tied behind their backs.
Authorities said they were targeting the Venezuelan gang Tren de Aragua,
though they also said only two of the 27 immigrants arrested were gang
members. They gave few details on the arrests.
But the apartments of dozens of U.S. citizens were targeted, residents
said, and at least a half-dozen Americans were held for hours.
The immense show of force signaled a sharp escalation in the White
House’s immigration crackdown and amplified tensions in a city already
on edge.
“To every criminal illegal alien: Darkness is no longer your ally,”
Homeland Security said in a social media post accompanying the video,
which racked up more than 6.4 million views. “We will find you.”
But Tony Wilson, a third-floor resident born and raised on Chicago's
South Side, sees only horror in what happened.
“It was like we were under attack,” Wilson said days after the raid,
speaking through the hole where his door knob used to be. Agents had
used a grinder to cut out the deadbolt, and he still couldn't close the
door properly, let alone lock it. So he had barricaded himself inside,
blocking the door with furniture.
“I didn’t even hear them knock or nothing,” said Wilson, a 58-year-old
U.S. citizen on disability.
Dreams and decay
The raid was executed in the heart of South Shore, an overwhelmingly
Black neighborhood on Lake Michigan that has long been a tangle of
middle-class dreams, urban decay and gentrification.
It's a place where teams of drug dealers troll for customers outside
ornate lakeside apartment buildings. It has some of the city’s best
vegan restaurants but also takeout places where the catfish fillets are
ordered through bullet-proof glass.
It has well-paid professors from the University of Chicago but is also
where one-third of households scrape by on less than $25,000 a year.
The apartment building where the raid occurred has long been troubled.
Five stories tall and built in the 1950s, residents said it was often
strewn with garbage, the elevators rarely worked and crime was a
constant worry. Things had grown more chaotic after dozens of Venezuelan
migrants arrived in the past few years, residents said. While no
residents said they felt threatened by the migrants, many described a
rise in noise and hallway trash.
Owned by out-of-state investors, the building hasn’t passed an
inspection in three years, with problems ranging from missing smoke
detectors to the stench of urine to filthy stairways. Repeated calls to
a lead investor in the limited liability company that owns the building,
a Wisconsin resident named Trinity Flood, were not returned. Attempts to
reach representatives through realtors and lawyers were also
unsuccessful.
Crime fears spiked in June when a Venezuelan man was shot in the head
“execution-style,” the Department of Homeland Security said in a
statement. Another Venezuelan was charged in the death.
Days after the raid, the doors to dozens of the building’s 130
apartments hung open. Nearly all those apartments had been ransacked.
Windows were broken, doors smashed, and clothes and diapers littered the
floors. In one apartment, a white tuxedo jacket hung in the closet next
to a room knee-deep in broken furniture, piles of clothing and plastic
bags. In another, water dripping from the ceiling puddled next to a
refrigerator lying on its side. Some kitchens swarmed with insects.
Wilson said a trio of men in body armor had zip-tied his hands and
forced him outside with dozens of other people, most Latino. After being
held for two hours he was told he could leave.
“It was terrible, man,” he said. He’d barely left the apartment in days.
A city under siege?
Chicago, the White House says, is under siege.
Gang members and immigrants in the U.S. illegally swarm the city and
crime is rampant, President Donald Trump insists. National Guard
soldiers are needed to protect government facilities from raging
left-wing protesters.
“Chicago is the worst and most dangerous city in the World,” he posted
on Truth Social.
The reality is far less dramatic. Violence is rare at protests, though
angry confrontations are increasingly common, particularly outside a
federal immigration center in suburban Broadview. And while crime is a
serious problem, the city's murder rate has dropped by roughly half
since the 1990s.
Those realities have not stopped the Trump administration.
What started in early September with some arrests in Latino
neighborhoods, part of a crackdown dubbed “Operation Midway Blitz,” has
surged across Chicago. There are increasing patrols by masked, armed
agents; detentions of U.S. citizens and immigrants with legal status; a
fatal shooting; a protesting pastor shot in the head with a pepper ball
outside the Broadview facility, his arms raised in supplication.
By early October, authorities said more than 1,000 immigrants had been
arrested across the area.
The raids have shaken Chicago.
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The apartment building at 7500 South Shore Drive in Chicago, which
was raided by ICE agents is seen on Oct. 8, 2025. (AP Photo/Paul
Beaty)
“We have a rogue, reckless group of heavily armed, masked
individuals roaming throughout our city,” Mayor Brandon Johnson said
after the Sept. 30 raid. “The Trump administration is seeking to
destabilize our city and promote chaos.”
To Trump’s critics, the crackdown is a calculated effort to stir
anger in a city and state run by some of his most outspoken
Democratic opponents. Out-of-control protests would reinforce
Trump’s tough-on-crime image, they say, while embarrassing Johnson
and Illinois Gov. JB Pritzker, seen as a possible Democratic
presidential contender.
So the South Shore raid, ready-made for social media with its
displays of military hardware and agents armed for combat, was seen
as wildly out of proportion.
“This was a crazy-looking military response they put together for
their reality show,” said LaVonte Stewart, who runs a South Shore
sports program to steer young people away from violence. “It’s not
like there are roving bands of Venezuelan teenagers out there.”
Officials insist it was no reality show.
The operation, led by U.S. Customs and Border Protection, was based
on months of intelligence gathering, according to a U.S. official
who was not authorized to discuss the matter publicly. The
building's landlord told authorities that Venezuelans in about 30
units were squatters and had threatened other tenants, the official
said, adding that the building’s size necessitated the show of
force. Immigration agencies declined further comment.
Even before the “Midway Blitz,” Trump's election had whipsawed
through Chicago's Latino communities.
Stewart said Venezuelan children began disappearing from his
programs months ago, though it's often unclear if they moved,
returned to Venezuela or are just staying home.
“I had 35 kids in my program from Venezuela," he said. "Now there’s
none.”
A wave of migrant newcomers
The raid echoed through South Shore, pinballing through memories of
the surge in violence during the 1990s drug wars as well as economic
divides and the sometimes uncomfortable relations between Black
residents and the wave of more than 50,000 immigrants, most Latino,
who began arriving in 2022, often bused from southern border states.
Chicago spent more than $300 million on housing and other services
for the immigrants, fueling widespread resentment in South Shore and
other Black neighborhoods where the newcomers were settled.
“They felt like these new arrivals received better treatment than
people who were already part of the community,” said Kenneth Phelps,
pastor at the Concord Missionary Baptist Church in Woodlawn, a
largely Black neighborhood.
It didn't matter that many migrants were crowded into small
apartments, and most simply wanted to work. The message to
residents, he said, was that the newcomers mattered more than they
did.
Phelps tried to fight that perception, creating programs to help new
arrivals and inviting them to his church. But that stirred more
anger, including in his own congregation.
“I even had people leave the church,” he said.
In South Shore it’s easy to hear the bitterness, even though the
neighborhood's remaining migrants are a nearly invisible presence.
“They took everyone’s jobs!” said Rita Lopez, who manages
neighborhood apartment buildings and recently stopped by the scene
of the raid.
“The government gave all the money to them — and not to the
Chicagoans,” she said.
Changing demographics and generations of suspicion
Over more than a century, South Shore has drawn waves of Irish,
Jewish and then Black arrivals for its lakeside location, affordable
bungalows and early 20th-century apartment buildings.
Each wave viewed the next with suspicion, in many ways mirroring how
Black South Shore residents saw the migrant influx.
Former first lady Michelle Obama’s parents moved to South Shore when
it was still mostly white, and she watched it change. A neighborhood
that was 96% white in 1950 was 96% Black by 1980.
"We were doing everything we were supposed to do — and better,” she
said in 2019. “But when we moved in, white families moved out.”
But suspicion also came from South Shore’s Black middle-class, which
watched nervously as many housing projects began closing in the
1990s, creating an influx of poorer residents.
“This has always been a complex community,” Stewart said of those
years.
“You can live on a block here that’s super-clean, with really nice
houses, then go one block away and there’s broken glass, trash
everywhere and shootings,” he said. “It’s the weirdest thing and
it's been this way for 30 years.”
___
Associated Press reporters Aisha I. Jefferson in Chicago, Elliot
Spagat in San Diego and Claudia Lauer in Philadelphia contributed to
this report.
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