On Sept. 9, 2025, Immigration and Customs Enforcement launched “Operation Midway Blitz” in Chicago and suburban Cook County, purportedly to seize “criminal illegal aliens” who the agency claims flocked to Chicago because of Illinois’ sanctuary policies. The past two months, however, have made it clear that the actual effect has clearly been to harass, abuse and intimidate the residents of a city that Republicans in general — and President Donald Trump — in particular have distinctly loathed.
The images coming out of Chicago have been shocking — ICE and Customs and Border Protection agents, armed with long guns, sailing down the Chicago River. Agents spraying a Protestant priest with pepper spray at point blank range, then later shooting the same man in the head with a pepper ball from a rooftop as he peacefully stands near the Broadview detention facility. Hauling a day care worker out of schools, pointing guns at passers-by, forcing a neighborhood to cancel a kids’ Halloween parade after blasting the area with tear gas seemingly without justification.
Residents never quite know when or where the federal agents will pop up, leaving the whole city on edge.
Now, to be clear, ICE and CBP lack the manpower to impose a consistent iron fist across Chicago and Cook County. The Department of Homeland Security is cagey, for example, about how many people it has on the ground in Chicago, but deposition testimony suggests roughly 200 agents; for comparison, the Chicago Police Department has about 8,000 beat cops and about 11,500 officers overall — and they don’t have to worry about the suburbs.
But ICE and CBP have been effective at engaging in what can be thought of as “stochastic authoritarianism,” by surging into places seemingly at random. Residents never quite know when or where the federal agents will pop up, leaving the whole city on edge.
At the heart of all this is Gregory Bovino, a CBP chief with an unsettling penchant for 1940s-era fashion who was put in charge of DHS’ earlier raids in Los Angeles and is now a “commander-at-large” in charge of Midway Blitz.
His tactics have become so aggressive that a federal district judge, Sara Ellis, recently ordered him to check in with her each day to verify that neither he nor those under his command were using excessive force — a ruling that the appellate courts quickly put on hold. He has admitted to racial profiling when talking to a reporter (and then later denying saying what he said into a microphone). He has been seen throwing what appears to be a tear gas canister into a crowd — and after a court hearing over allegations of excessive use of such weapons, his men defiantly put a tear gas canister on the dashboard of the car driving him away.
It is possible, however, that Bovino and the aggressive tactics he referred to first as “exemplary” and then later as “more than exemplary” may have gone too far.
On Thursday morning, Judge Ellis not only issued a preliminary injunction significantly curtailing federal agents’ use of (so-called) less-lethal weapons, on the grounds that it was violating protesters’ First Amendment rights, but she also berated them and their leadership both for their actions and their dishonesty.
This setback comes at a bad time for ICE’s effort to scale up its staffing.
Ellis accused Bovino of lying when he claimed in sworn deposition testimony that he did not use force against a man he was videotaped tackling. She pointed out that after ICE officers tear-gassed and threatened protestors, everyone they detained was later released by the FBI without being charged for assault, and that an agent joked “have fun” as they lobbed tear gas at people.
In the end, Ellis concluded that the claims the feds made to justify their actions “lack credibility,” and that the “exemplary” behavior of the ICE, CBP and other federal agency officers under Bovino’s command “shocks the conscience.”








