CHICAGO — Olayemi Owoludun was still in high school when Donald Trump won the presidency in 2016. He was too young to vote, but not too young to feel its impact.
A “terrified” friend who was an immigrant fell off the grid months after Trump’s first inauguration, he recalls. He was worried about his undocumented friend and their Lincoln Square neighborhood. Without disclosing the friend’s name or her birthplace for safety concerns, Owoludun remembers her being afraid of being deported back to her home country.
“Then she came back,” he said. “But when he [Trump] got reelected [in 2024], she fell back, again. She wasn’t reaching out to anyone. It was very hard to get in contact with her.”
During an afternoon break in September from his job as a hotel concierge, the 24-year-old declined to say who he voted for in 2020 or 2024, citing privacy concerns. But after the 2024 election, he said he understood what a Trump victory could mean for his friend and the immigrant communities he works with in Evanston. The city is on the North Side of Chicago and has a long-established Black community shaped by redlining and housing segregation, especially during and after the Great Migration.
“It’s really disheartening knowing how long and how hard people fight to get here — and even though they wouldn’t be considered legal, they’re still humans at the end of the day,” Owoludun said. He’s the son of Nigerian-born, naturalized parents.
Many Black immigrants in the Chicago metro area have settled in majority-Black neighborhoods where earlier generations of their families already live — including Evanston and Rogers Park on the North Side, and Woodlawn and South Shore on the South Side. There are 69,484 Black immigrants in the Chicago metro area originally from a country in Africa, making up 5.2% of the city’s population, according to an American Community Survey analysis of the 2023 Census.
Owoludun’s reluctance to share his political stance came two days after the U.S. Department of Homeland Security launched “Operation Midway Blitz,” an immigration enforcement effort targeting undocumented people in Chicago and across Illinois.
Trump escalated his administration’s immigration crackdown by signing executive orders to deploy the National Guard into sanctuary jurisdictions that were seen as defiant. These largely Democratic-led municipalities, including Chicago, have policies that limit cooperation from local police with the federal government to identify and assist with removing an undocumented person.
As the federal takeover of Washington, D.C., neared its end on Sept. 10, Trump turned his attention to Chicago, again calling for a crackdown on violent crime despite both cities reporting their lowest homicide rates in decades. In response, Illinois Gov. JB Pritzker, a Democrat, publicly condemned the threat of federal intervention. Days of peaceful protests erupted downtown, and Mayor Brandon Johnson, also a Democrat, signed an executive order directing local police not to cooperate with ICE.
While some Black Chicago residents praised Illinois officials’ pushback against the federal crackdown as a sign of unity, many people that Capital B spoke to remain uneasy. With Operation Midway Blitz keeping ICE agents active in the city, they worry it’s only a matter of time before more federal troops line their blocks.
At a recent community event hosted by Healthy Hood Chicago, and in conversations with a group of young Black men near the Howard Street Red Line stop, several Chicago residents, including Owoludun, said they had witnessed at least one ICE arrest or traffic stop over the course of a week since Labor Day.
Unlike Owoludun, some longtime Chicago residents say they were conflicted about continuing to support the thousands of African, Caribbean, South and Central American asylum-seekers sent to the city by Texas Gov. Greg Abbott beginning in 2022.
At the same time, a 2024 Gallup poll found that a record 55% of Americans view the influx of immigrants as a “critical threat.” And while many of these Black Chicago residents oppose the current administration’s use of federal troops to override local policies and separate families under the guise of law and order, they’re also concerned their own communities — already facing underinvestment, housing shortages, and rising costs — are still being overlooked.
‘It’s more about numbers … at this point’
Trump’s first federal takeover began in Washington, D.C., in August, carried out under the city’s Home Rule Act with National Guard support and law enforcement aid from six Republican-led states. Over the 30-day operation, officers targeted low-income neighborhoods, leading to the arrests of mostly Black men and more than 900 immigrants, according to a Washington Post analysis. A 2022 Pew Research Center report found that the D.C. metro area is home to the third-largest population of Black immigrants in the U.S., with an estimated 260,000 residents.
Valerie Lacarte, a senior policy analyst at the nonpartisan Migration Policy Institute, said efforts to meet Trump’s goal of 15 million deportations could lead to overpolicing in low-income Black and brown communities, overcrowded jails for those unable to post bail, and potentially more prison sentences if convictions follow.
“It becomes an unfocused enforcement plan because they’re more interested in hitting those targets. The people, who are carrying out those plans, are not offering due process and making sure they’re arresting the right people,” Lacarte said. “Because it’s more about numbers, I think, at this point.”
For residents in Chicago,The Washington Post’s reporting could read like a cautionary tale, she said. Since 2020, the city has been responsible for nearly 240,000 international migrants — fueling both support and strain in neighborhoods already grappling with underinvestment.
Back in Rogers Park on W. Howard Street, a trio of Black women who live near the Caribbean American Baking Company, had conflicting views about a possible federal takeover. Yet, they all agreed that snatch-and-grab robberies have been a public safety issue citywide.
“We do have a lot of crime going on in the city that’s moving from the South to the North and into the suburbs,” said Walterine Brock, 73, and originally from Mississippi. She did acknowledge the mayor’s office reports a drop in crime.
Ernestine Williams, 68, a Chicago native, and Lorna Garbutt, 72, a naturalized citizen from Belize, said they don’t believe Black residents should involve themselves in what they view as a politically charged immigration crackdown. They pointed to a long history of police disproportionately targeting Black people for everyday activities like walking or driving. Brock agreed. There’s also a recent U.S. Supreme Court ruling that allows ICE agents to consider race as one factor during enforcement actions near the border or in certain raids.
Lacarte said the ruling sets a precedent by validating “all the stigma and all the stereotypes out there” — including what law enforcement imagines when they think, “Who’s a Latino? What do they look like?” — and warned it could influence broader policing in Black communities.
“From the Black community’s perspective, I don’t see this going anywhere positive,” said Lacarte, who was born in Canada to Haitian-born parents. “Even if Black people don’t think they are necessarily the main target at this time, you know, they can easily be.”

‘We in a dark time right now’
Decades prior to the 2022 influx of asylum seekers into Chicago’s North and South sides, there had been an increase of immigrants from countries such as Ethiopia, Eritrea, Ghana, Haiti, Jamaica, Mali, Somalia, and Senegal.
Many of the migrants bused from Texas to Chicago in 2022 had no idea where they were headed, Lacarte said. Among them were Black immigrants — from Africa, the Caribbean, and Spanish-speaking countries in Central, Latin, and South America — who also identify as Black, she added.
“It seemed, perhaps at a time, like it was a haven for them to come and get housing and food and everything, and yet,” Lacarte said about the emergency situation that included temporary housing. “Without a permanent solution to legal status, that all can be taken away by the stroke of a pen.”
Since the influx of migrants, some Black Chicagoans said they’ve been forced to compete for resources they’ve needed long before the newcomers arrived. Much of their frustration stems from a 2024 lawsuit that revealed $30 million in taxpayer funds had been allocated since 2022 to house migrants. That money, some argue, has come at the expense of long-standing needs in Black communities, particularly housing and food access.
Dana Mosley, a social worker who has lived in Chicago on and off for 23 years, said because of this, many older Black residents feel unmoved by the threat of federal immigration crackdowns.
Though the administration’s nationwide immigration crackdowns have mostly focused on undocumented migrants and asylum seekers from Central and South America, Black immigrants haven’t been spared. In Palm Beach, Florida, Rony Dieujuste — a Haitian man — was detained by ICE after a minor arrest. Dieujuste has been held in ICE detention since May.
In a phone interview, Mosley described the 2-to-1 sentiment among the retired women Capital B spoke to — Brock, Garbutt, and Williams — as being “desensitized” after years of living in overpoliced communities and “not in fear.”
Mosley empathizes with Latino families, who are afraid to leave their homes to go to the grocery store or work in fear of being stopped by ICE.

“I feel for these people with immigration issues, but I have been Black my whole life,” said Mosley, who also identifies as Native American. “I can’t walk around in fear. My son, who is 17, commutes … he can’t live in fear.”
Recoechi, a Chicago community organizer with Healthy Hood Chicago, said that in social circles and online, he often finds himself reminding both elders and youth not to frame this administration’s actions as a matter of race or culture.
“It’s not ‘us against them,’” the 29-year-old rapper from the Southeast Side said. “We in a dark time right now, and the work of the oppressor has worked on us, but we have to wind that sh*t back.”
Lacarte praised advocacy groups such as the Chicago Coalition for Intercommunalism, which hosts quarterly community gatherings at Healthy Hood Chicago’s South Damen Avenue headquarters. Their goal, she said, is to “ease people and remind them that becoming an oppressor yourself is not going to solve the issue either.
“And adopting that type of language toward other people who are in need today is not going to erase the systemic issues that those communities face.”
Owoludun, the hotel concierge, agrees.
“Instead of trying to weaponize this situation and criminalize people who are in unfortunate situations like these, we should be able to be a refuge for them,” he said. “That’s what the world needs.”
Great Job Christina Carrega & the Team @ Capital B News Source link for sharing this story.