For most of the fall, President Donald Trump’s immigration agents have set out every day to scour Chicago neighborhoods where immigrants live. On Friday, Operation Midway Blitz fanned out across the wealthier white communities on the North Side where they work.
Throughout the day, caravans of federal agents hit neighborhoods that had so far avoided serious confrontations.
In Lakeview, agents threw tear gas into the street, even as their use of chemical agents has drawn intense scrutiny from a federal judge. Masked officials arrested a man at the Laugh Factory comedy club. They detained a man at a gas station near the tony Latin School where the city’s elite send their children.
What to know about Donald Trump’s immigration enforcement raids in Chicago
A spokesperson for the U.S. Department of Homeland Security did not immediately return a request for comment. But Lincoln Park Ald. Timmy Knudsen, 43rd, said masked immigration agents hit “every corner of the ward” he represents, one of the city’s wealthiest communities.
A video taken at Racine and Schubert avenues shows four agents surrounding a Latino man and leading him away from million-dollar properties, placing him into an SUV and driving off.
Ald. Scott Waguespack, 32nd, said agents grabbed a landscaper and two construction workers and appeared to be going through side streets picking up workers. He got into a shouting match with an immigration agent near St. Mary of the Angels School because they were doing U-turns and “driving like lunatics” near children doing a fun run.
Knudsen approached masked agents in another area and asked them questions he learned through “know your rights” trainings as well as his previous work handling asylum cases.
“What are you doing here? What are you looking for? Do you have a warrant?” he said he asked.
They didn’t respond.
Instead, activists confronted agents, shouting at them and blowing their whistles to alert the community.
“My hope is them whistling and yelling at least keeps ICE moving along,” Knudsen said.Midafternoon, agents tear-gassed the Lakeview neighborhood near Lakewood Avenue and Henderson Street after a crowd of residents demanded they leave.
Neighbors and congressional staffers said the chaotic scene unfolded when federal immigration agents arrested at least one construction worker at a home on North Lakewood Avenue.
Employees appeared to be on a lunch break out front when agents jumped over the gate to get to them, residents told the office of U.S. Rep. Mike Quigley, a Chicago Democrat.
The home was left half-finished with at least four ladders hanging on the side of the building and tape in the windows.
Neighbors with whistles confronted the federal immigration agents and demanded they get out.
Videos from the scene show two vans used by the agents, one of which was slowly driving backward. Most of the gathered residents were on the sidewalk with a few walking in the street near the vehicles, chanting “traitors” and “go home.” They didn’t appear to touch it or the agents before tear gas is deployed.
Bruce Turner, 64, came outside when he heard the commotion and called the tear gas use “unprovoked.”
“They have one car going backwards, one car going forward, and people are … yelling at them,” he said. “Nobody touched them.”
Another resident, who declined to give her name for fear of retribution, said she was at home working when she heard screaming and whistles, telltale signs that preface federal immigration agent sightings. She, too, criticized the feds’ use of tear gas.
“There was no warning, no warning at all,” she said.
Ring camera footage captured when agents took a worker who had been replacing windows and siding at Kevin Eberhardt’s home. In an interview, Eberhardt told the Tribune he had been in Toronto at the time of the incident but is flying back to deal with the aftermath.
“ICE illegally gained entry to our home today,” he wrote in an email to Ald. Bennett Lawson’s office. “Below are videos to our ring camera where you see that they climbed our fence, even though multiple people were telling them they need a warrant.”
He called the incident “shocking” and upsetting.
“It’s just chaos,” Eberhardt said. “I’m not a lawyer. I do follow this. It is what it is. But it seems like a lot of unlawful things are occurring.”
Lawson, 44th, who represents Lakeview and Wrigleyville, released a statement condemning the actions.
“ICE’s un-American and undemocratic tactics of fear and intimidation in our neighborhoods are a direct attack on everything Chicago stands for — inclusion, compassion and love,” Lawson said. “We have a proud history of welcoming people of all backgrounds in our community and our commitment to those principles are stronger now than ever.”
Outside the Nettelhorst Fine and Performing Arts School on Broadway in Lakeview, a neighborhood resident volunteering as a federal immigration agent-watcher kept an eye out for agents. While the neon-vest-clad volunteer stood guard, a man dropped off a set of orange whistles into a Little Free Library box outside the school. He said he was 3D-printing the whistles by the hundreds.
Videos circulating on social media showed agents within blocks of DePaul University’s Lincoln Park campus. In a message to students and faculty members Friday, DePaul President Robert Manuel said the school had received confirmed reports of nearby federal immigration activity. He noted that classes, research and other campus activities were proceeding as scheduled.
“The safety and well-being of our students, faculty, and staff are our highest priority,” Manuel wrote. “Now more than ever, we must look out for one another.”
The Laugh Factory, in a social media post Friday, said one of its employees was among those detained. According to the comedy club, its night manager was detained by “masked federal agents” outside of its Lakeview location at 3175 N. Broadway.
In a call with the Tribune Friday night, Laugh Factory’s president of operations Curtis Flagg said that the manager was walking with his mother from the direction of Belmont Avenue and Broadway when he saw a man getting detained. As he approached, the manager tried to intervene verbally, Flagg said.
“No physical contact, no touching,” Flagg said. “Then they grabbed him.”
Flagg, who was not at the scene but was called during the confrontation and received a flurry of videos of what had happened afterward, said that agents apparently tackled the manager onto the ground with his mother in tow. The manager was then placed in an unmarked vehicle that proceeded to speed east onto Belmont then south on Lake Shore Drive.
Heading into events planned for Friday night, Flagg said, “A lot of comedians and staff do not feel safe or comfortable coming in.”
But the club is keen to carry on.
“The one thing that brings us together is comedy,” he said. “It is the medium that (allows) you to leave it all at the door, come enjoy yourselves (and) laugh in a world where there’s just nothing but tears. … I will be darned if I allow this administration to stop the people of Chicago from being able to do that.”
In a statement, Chicago police said officers observed federal agents engaged in a “physical altercation” with two individuals after responding to a call of a battery in progress near the comedy club at Belmont Avenue and Broadway at about 9:20 a.m. As a crowd gathered, officers “worked to de-escalate and conduct crowd control to ensure all those who had gathered at the location remained safe,” police stated.
Officers did not make any arrests and left after the area was cleared, police added. Flagg said the club was informed the manager was in federal custody and awaiting charges as of 6 p.m. Friday.
Earlier this week, federal immigration officials were in Little Village — a Southwest Side neighborhood that is home to Chicago’s largest Mexican American population — on Thursday for the second time in two days. Half a dozen people were detained in the raids Thursday, including a 16-year-old U.S. citizen, a student at Benito Juárez Community Academy in the Pilsen neighborhood. At least seven people were also taken into custody Wednesday.
U.S. District Judge Sara Ellis, meanwhile, ordered Border Patrol Cmdr. Gregory Bovino to appear in court personally on Tuesday as part of an ongoing inquiry into potential violations of her restraining order on crowd-control tactics used during “Operation Midway Blitz,” including tear gas.
In addition to being ordered into court on Tuesday, Bovino will have to testify under oath about the Little Village incidents and other controversial use-of-force decisions in an upcoming deposition.
Ellis is scheduled to hold a hearing on a full injunction in November.
Chicago Tribune reporters Talia Soglin, Kate Armanini, Tess Kenny, Jason Meisner, Laura Rodríguez Presa and Kate Perez contributed.