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.”
This setback comes at a bad time for ICE’s effort to scale up its staffing. That the agency is struggling to hit its goal of 10,000 additional field officers is already well-documented, and the ongoing chaos of the federal government shutdown must make federal employment look even less appealing. But hearings like this pose an additional, serious threat. DHS insists that the recent stories about applicants failing physicals and written tests overstates their hiring challenges because the department expects roughly 85% of its new staffing to come from current and former local law enforcement officers, who go through a different process.
But why would local police officers change jobs to work for an agency that is among the least popular in America, whose officers are regularly yelled at and berated by locals — including a pajama-wearing former prosecutor — all for less pay, and now the increased risk of constant judicial criticism and oversight.
The sort of low-level arrests ICE is making is already hurting morale; increasingly angry oversight will only make that worse. However much criticism is directed at police departments and their current practices, support for them remains high — about 75% of U.S. adults have confidence in their local police, according to a May 2025 Gallup poll. Why would someone quit a job with generally better pay and higher social respect? (And so far, efforts to poach local police seem to be failing.)
I also hope the public takes the right lesson from Judge Ellis’ justifiable anger at what she saw as Bovino’s lies: not that this reflects some sort of unique cultural failure in the CBP — notorious for its cowboy culture — but that she is shedding light on a much more persistent, deeper problem with policing. Police dishonesty, even on the stand and under oath, is so common that it has its own name (“testilying”), and it has forced prosecutor offices to create what are called “Brady Lists” of officers they will not put on the stand out of fear they’ll commit perjury.
If there is any silver lining to what ICE and CBP are doing in Chicago, it is that it may make the public more aware of just how common this practice is. The feds keep insisting on giving implausible excuses despite ample cellphone and body-worn camera evidence disproving their accounts — to the point that even usually staid federal court hearings result in judges berating federal officials in open court for their dishonesty.
The extremeness of the behavior in which ICE, CBP and Bovino himself engage in may be uniquely shocking, but the ways they attempt to spin and disavow it are not.
