Trump sent federal troops to 'save' Chicago. The 'Midway Blitz' raids forced the Windy City to defend itself

In the middle of the night on Sept. 30, Eboni Watson heard an unusual buzzing sound.

The noise came from 10 drones and three Black Hawk helicopters, Watson says, which dropped armed men on neighbouring rooftops in Chicago's South Shore neighbourhood. On the ground, Watson saw agents deploy out of unmarked cars and rental vans.

“It was bringing people outside because it was such a disturbance. You have people that was thinking UFOs and stuff was landing,” Watson, who livestreamed the situation, told CBC News.

But it wasn't an alien invasion. It was a federal immigration raid involving hundreds of agents.

Eleanor McMullen-Webster was among those arrested.

“When I opened that door, I tell you, I saw that little red light, and that gun was right in my face,” McMullen-Webster told CBC.

Federal agents handcuffed the 64-year-old retiree and her husband, she says, directing them into an apartment where Venezuelan migrants were lined up against a wall.

The raid on the South Shore apartment complex was part of a larger initiative by the Department of Homeland Security (DHS) to capture the “worst of the worst criminal illegal aliens” in Illinois, according to a press release. Codenamed Operation Midway Blitz, the mission was to capture undocumented migrants allowed to “roam free on American streets” due to the state’s sanctuary policies.

That night, authorities arrested 37 immigrants, mostly Venezuelans, though none have been charged.

Immigration and Customs Enforcement (ICE) says two of them are members of Tren de Aragua, a Venezuelan transnational criminal group the U.S. designated a terrorist organization in February, but didn't release names. One of those men denied any association with the organization in an interview with ProPublica.

WATCH | Detained without explanation:Eleanor McMullen-Webster, a 64-year-old retired Chicagoan, says she and her husband were arbitrarily arrested by federal agents in the middle of the night, and alleges authorities would not explain why they were detained.

After being held for more than an hour, McMullen-Webster and her husband were released, without an explanation.

“I felt this small,” said the Chicago resident, still furious at the “disrespectful” way she was treated.

President Donald Trump’s immigration crackdown has faced sharp criticism, including from former president Barack Obama and Pope Leo, who is from Chicago. Both admonished the vilification of migrants.

WATCH | Pope decries treatment of migrants:

But the idea of “saving” Chicago has been ongoing for years.

While running for president in 2016, Trump frequently invoked the city’s violent crime rate, calling Chicago a “war zone” and saying minorities in “inner cities” were “living in hell.”

Two weeks before his assassination, MAGA influencer Charlie Kirk — a Chicago native — spoke out in favour of Trump's efforts to apprehend "illegal criminals” trying to “take over” the U.S. “from within.” At Kirk’s memorial, Trump said one of the last things Kirk said to him was, “Please, sir, save Chicago.”

“We're going to do that,” Trump told the crowd. “We're going to save Chicago from horrible crime.”

But in the wake of Operation Midway Blitz, Chicagoans themselves are divided over who the criminals are — and who is ultimately responsible for keeping their city safe.

Troops sent to ‘straighten out’ Chicago

The helicopter-assisted ICE raids took place three weeks after Trump threatened the city in a post on Truth Social. It included an image of him as a military commander with the caption, “I love the smell of deportations in the morning,” a reference to the 1979 war film Apocalypse Now.

Trump’s rocky relationship with Chicago goes back years. In 2014, he built a 20-foot-tall steel sign spelling out his name on the city’s Trump Tower. The move drew widespread backlash, including from then-mayor Rahm Emanuel.

As president, Trump blasted the city’s tolerance of illegal immigration, saying violence in Chicago was “worse than some of the places … where you have wars going on.” He frequently took aim at local officials on social media, threatening to “send in the Feds” in January 2017.

WATCH | Call for solidarity:People should ‘put our egos to the side’ and build solidarity across racial lines, says Eboni Watson, a South Shore resident who videotaped the federal immigration raid on a neighbouring apartment complex.

Crime in “sanctuary” cities has been a focal point for the second Trump administration. After deploying the National Guard in August to address the “complete and total lawlessness” in Washington, D.C., he again vowed to send federal troops to “straighten out” Chicago.

Robert Reich, a former U.S. secretary of labour, suggested it's all a concerted effort to suppress the vote in the 2026 mid-term elections.

“He is saying to himself and maybe others quietly, this is a way to intimidate [residents],” Reich said. “‘If they're just afraid to be very public in any way, then I win, because they're not going to vote.’”

‘Absolute betrayal’ of American people

The force used by federal agents in the South Shore apartment complex is far from isolated.

In Evanston, Ill., a car was following a vehicle of DHS officers when agents slammed on the brakes, resulting in a crash. While arresting the activists, one of whom was severely beaten by officers, an immigration agent threatened to shoot a civilian filming the arrests.

“I believe that they're acting with total authority, but without any sort of oversight at all, and they should be held accountable for their actions,” said local resident David Brooks, who had a pistol pointed at him.

WATCH | Threatened with a gun:In this video shot by David Brooks, a border patrol agent shouts, ‘Get back or I’m [going to] shoot you,’ then points his pistol at the Evanston, Ill., resident seconds later. The agent would not give Brooks his name and badge number in the aftermath.

Michael Rodriguez, a representative for Chicago’s Little Village neighbourhood, characterized the immigration raids as an “absolute betrayal” of the U.S. Constitution and the American people.

“This is a disgrace to our country, to our legacy," he said. "It will live in infamy.”

Democratic Chicago committeeman Raymond Lopez says the violent nature of the raids have made his constituents — many of whom are long-term undocumented, mostly Mexican immigrants — fearful of going outside.

Danielle Carter-Walters, vice-president of conservative activist movement Chicago Flips Red, speaks on behalf her group at a subcommittee hearing on border security and immigration. (Zoe Leigh/Chicago Flips Red)‘Black Americans vs. brown illegals’

Despite growing opposition, some Chicago residents have welcomed Trump’s aggressive actions as a way to keep the city safe.

“When you place unvetted gang members into our buildings amongst us with our kids, then you put us in danger. And that's what we have seen in our communities,” said Danielle Carter-Walters, vice-president of grassroots conservative movement Chicago Flips Red.

The current violent crime rate in Chicago is down about 40 per cent from 2023, which had the most reported incidents in the last decade, city data shows. Crime across Illinois has followed a similar downward trend, though rates of homicide and rape remain higher than the national average.

WATCH | Migrants flown into Chicago:Texas Governor Greg Abbott chartered a plane to send 100 migrants to Chicago in response to the city giving fines to buses that were ferrying migrants to the city. It is the latest escalation in a political fight over the unprecedented number of migrants crossing from Mexico into border states like Texas.

Ramona Paravola, operations manager of Chicago Flips Red, says poor, often Black neighbourhoods were forced to absorb newcomers under the Biden administration — including more than 30,000 from Texas.

“They are not spreading the load out,” said Paravola, who believes politicians knew that adding migrant shelters to an “affluent white neighbourhood” would face greater backlash.

Seeing migrants receive help that Black Chicagoans have been demanding for years is another source of resentment. In 2024, for example, city officials invested more than $300 million US to address the migrant crisis — money, they say, should have been invested into their communities first.

WATCH | Chicago isn't safe, group says:Danielle Carter-Walters, vice-president of grassroots conservative movement Chicago Flips Red, says Chicago Mayor Brandon Johnson has not kept her community safe from ‘illegal aliens’ who she says are ‘selling drugs, prostitution [and] threatening the citizens.’

“How does that happen when they told us that they didn't have these [funds]?” said Carter-Walters.

“It's not Black and brown people. It's Black Americans versus brown illegals,” said Paravola.

Paravola, whose husband is a retired Chicago police officer, says she supports pathways to citizenship for “Dreamers” who come to America, including undocumented migrants without violent criminal records.

“We're not racist,” she said. “We're just intelligent enough to see people as individuals, or as individual communities, and not Black and brown as a big lump.”

A federal immigration enforcement agent sprays Rev. David Black, of the First Presbyterian Church of Chicago, as he demonstrates outside the Broadview ICE facility on Sept. 19. (Ashlee Rezin/Chicago Sun-Times/The Associated Press)ICE facility ‘gates of hell,’ says pastor

Presbyterian minister Rev. David Black has witnessed the violent methods used against immigrants employed against protesters at the ICE detention facility in nearby Broadview, Ill.

Black was praying for ICE agents and calling on them to “repent” on Sept. 19 when officers on the roof of the facility shot him in the face, head and body with pepper balls.

Immediately after, video shows Black shouting, “God is watching you — and you will pay for this!”

“It seems like they've been testing out how much they can get away with … as they suppress free speech and try to dismantle the civil society of a major American city,” Black told CBC News.

WATCH | Pastor shot with pepper balls:Rev. David Black, pastor of the First Presbyterian Church of Chicago, recounts how he was shot by pepper balls by agents on the roof of the Broadview, Ill., ICE detention facility.

When Kat Abughazaleh, a congressional candidate, first visited the Broadview facility for a vigil in the summer, she said ICE “didn’t even board up the windows." Since then, she has witnessed the “one-sided violence” by ICE agents escalate.

“People were dragged, beaten,” she said.

Abughazaleh, a journalist, was thrown to the ground herself at multiple rallies. In one video that went viral, Abughazaleh can be heard hitting the asphalt after being shoved by immigration officers.

“They shot pepper bullets at the sidewalk and said, ‘Your First Amendment rights are on the sidewalk,’” she said.

WATCH | ICE fires tear gas, pepper balls:Journalist and Democratic congressional candidate Kat Abughazaleh describes how immigration enforcement agents confronted demonstrators in ‘full tactical gear,’ using tear gas and pepper bullets against the group outside the Broadview, Ill., ICE facility.

Meanwhile, Sister JoAnn Persch, who worked with migrants in the Chicago area for 40 years, was repeatedly denied access to provide spiritual care to detainees at the Broadview facility. Authorities cited “safety reasons.”

“All these years I've been right with immigrants, I've never felt they were going to attack me and surely I was not going to attack them,” said the 91-year-old nun, who was not allowed inside to visit migrants during a Nov. 1 mass.

WATCH | Persch barred from ICE facility:

Earlier this month, the spiritual coalition Persch was a part of sued the federal government for what they allege are violations of First Amendment rights to religious freedom.

Persch, a Sister of Mercy who got a state law passed in 2009 to allow pastoral workers into immigration facilities, said the situation made her “extremely sad.”

“There's just so many human rights being violated in that building. So we just have to keep working for human and religious rights,” said Persch, who died on Nov. 14.

JoAnn Persch, a Sister of Mercy who worked with migrants in Chicago for decades, tells 2,000 people at a mass outside the Broadview facility that they are not allowed to visit and give communion to detainees, on Nov. 1. (Bryan Sebastian/Coalition for Spiritual and Public Leadership)Border Patrol commander ‘outright lying’

Two months since the beginning of Operation Midway Blitz, federal authorities and Chicago locals still find themselves at odds on whether the mission to “save” Chicago has succeeded.

At the end of October, DHS Secretary Kristi Noem boasted that agents “arrested more than 3,000 illegal aliens including rapists, murderers and gang members” since September.

But a Chicago Tribune analysis of government records found that of 614 arrestees whose names were released by the Department of Justice, only 16 — or 2.6 per cent — had criminal histories.

U.S. Customs and Border Patrol Commander Greg Bovino has defended the agency’s tactics, asserting in an interview that their “operations are airtight — legal, ethical and moral.”

WATCH | Trump's war on Chicago:Chicago has become a model for U.S. President Donald Trump’s campaign against political opponents in American cities. CBC's Terence McKenna breaks down why Chicago is in the crosshairs of the ICE crackdown and how the city has tried to resist.

But the widespread use of force has led to judicial scrutiny of the government’s tactics in Chicago. Bovino was subpoenaed to appear in federal court about his agents’ use of force against protesters in the Chicago area, and in a 233-page ruling released Nov. 20, Judge Sara L. Ellis identified “inconsistencies” in his testimony.

Ellis said Bovino “appeared evasive” throughout his deposition, either providing “cute” responses to the plaintiffs’ questions or “outright lying.”

WATCH | Woman choked, pastor shot, tear gas used against protestors:

The judge wrote that videos contradicted Bovino’s claims that his agents’ use of force was justified.

Ellis’s ruling prevents federal agents from using tear gas against people who do not pose a threat. A federal appeals court paused the injunction on Nov. 19, calling it “overbroad” and “too prescriptive.”

DHS did not respond to multiple requests from CBC News to interview Bovino.

U.S. Border Patrol agents ultimately left Chicago in mid-November. Committeeman Rodriguez believes resistance efforts in the city were a large factor.

“It wasn't just the weather. I think [federal agents] knew they encountered people that weren't gonna take their BS,” he said. “We know what makes us safe. We keep us safe. Not Donald Trump.”

But Abughazaleh believes this fight won't be “over” for years.

“We're living in a horror movie,” she said. “A lot of our most important systems are being razed to the ground. But that does mean that we have an opportunity to build something better.”