On September 8, 2025, the Trump administration dramatically escalated its immigration enforcement agenda, launching a new series of federal operations targeting sanctuary cities, with Chicago and Boston at the epicenter. The Department of Homeland Security (DHS) announced "Operation Midway Blitz" in Illinois, a campaign aimed at undocumented immigrants with criminal records, and revealed a parallel effort, "Operation Patriot 2.0," in Massachusetts. These moves, as reported by Reuters, CBS News Chicago, and other outlets, have ignited fierce debate and resistance from local leaders, immigrant communities, and civil rights advocates.
"You can expect action in most sanctuary cities across the country," border czar Tom Homan declared on CNN over the weekend, signaling the administration’s broader intent. President Donald Trump, who has repeatedly clashed with Democratic-led cities over their sanctuary policies, appeared to relish the confrontation. In a now-walked-back post on Truth Social, he wrote, "I love the smell of deportations in the morning ... Chicago is about to find out why it’s called the Department of War." Later, facing backlash, Trump clarified, "We’re not going to war, we’re going to clean up our cities. We’re going to clean them up so they don’t kill five people every weekend. That’s not war. That’s common sense." (as cited by Article 1).
The official line from DHS describes Operation Midway Blitz as targeting "the worst of the worst criminal illegal aliens in Chicago," according to Assistant DHS Secretary Tricia McLaughlin. The agency cited 11 cases involving immigrants, mostly from Mexico and Venezuela, with records of arrest or convictions for serious crimes—such as gang activity, rape, kidnapping, and drug trafficking—who were released from local jails instead of being turned over to federal authorities (Reuters). "This ICE operation will target the criminal illegal aliens who flocked to Chicago and Illinois because they knew Governor Pritzker and his sanctuary policies would protect them and allow them to roam free on American streets," ICE stated.
Yet, on the ground, the picture is far more complicated. Reports of ICE arrests began on September 7, 2025, in Chicago’s Archer Heights neighborhood, including the detention of a local flower vendor. By Monday morning, federal agents were spotted in the West Lawn neighborhood near Midway International Airport. Local Alderwoman Jeylu Gutierrez, representing the predominantly Hispanic 14th Ward, reported at least five community members detained—some while waiting for a bus, others simply walking along the sidewalk. "This was never about arresting the worst of the worst, this is about terrorizing our communities," Gutierrez said at a press conference (Reuters).
Community groups and activists have mobilized rapidly in response. The Illinois Coalition for Immigrant and Refugee Rights urged residents to know their rights and document any encounters with ICE agents. "Chicago is fighting back. We will keep each other safe," said Rey Wences, senior director of deportation defense for the coalition. West Lawn resident Eddie Guillen canvassed the neighborhood, distributing "know your rights" materials to fearful neighbors. "Just disgusted. You know, it’s one of those things where we have to do better and look after the community," Guillen told CBS News Chicago.
Local officials, meanwhile, have voiced outrage over the lack of communication from federal authorities. Both Illinois Governor JB Pritzker and Chicago Mayor Brandon Johnson, Democrats, said they received no official notice or coordination from DHS regarding the operation. Mayor Johnson, who signed an order last weekend directing local law enforcement not to cooperate with federal agents, expressed grave concerns: "We are concerned about potential militarized immigration enforcement without due process because of ICE’s track record of detaining and deporting American citizens and violating the human rights of hundreds of detainees." Johnson also established a new initiative aimed at protecting residents’ rights.
Governor Pritzker, for his part, dismissed the administration’s rationale as political theater. "This isn’t about fighting crime," he posted on social media. "That requires support and coordination—yet we’ve experienced nothing like that over the past several weeks." Pritzker even suggested that Trump’s threats to deploy the National Guard might be a "dress rehearsal" for using the military to influence the 2026 midterm congressional elections (Reuters).
President Trump, undeterred, continued to blame local leaders for the city’s challenges. In another Truth Social post, he wrote, "I want to help the people of Chicago, not hurt them. Only the criminals will be hurt! We can move fast and stop this madness." He also referenced Illinois Governor JB Pritzker, claiming he was still waiting for a call from the governor asking for federal help to fight crime—a call Pritzker has made clear he will not place.
Resistance to the crackdown has been widespread. The city of Evanston, an urban suburb of Chicago, issued a statement warning residents of impending ICE raids and urging them to report sightings of law enforcement. In Boston, Mayor Michelle Wu vowed to challenge any enforcement efforts that cross legal lines, citing the Boston Trust Act. This law, first adopted in 2014 and amended five years later, restricts local law enforcement from collaborating with ICE on civil immigration matters, except in cases involving significant public safety threats. "For months, ICE has refused to provide any information about their activities in Boston and refuses to issue warrants, while we hear reports of ICE agents taking parents as they are dropping their kids off at school. That does not make our community safer," Wu said in a statement, adding, "We expect that federal law enforcement will abide by the constitution and laws of this City, Commonwealth, and country, and we are prepared to take legal action at any evidence to the contrary."
The federal government has not been shy about pushing back. On September 8, 2025, the Justice Department sued Boston over its sanctuary policies. Attorney General Pam Bondi criticized the city as "among the worst sanctuary offenders in America," stating, "If Boston won’t protect its citizens from illegal alien crime, this Department of Justice will." Wu responded defiantly, "We will not yield."
The broader context for these operations is a years-long tug-of-war between the Trump administration and sanctuary cities. Previous attempts to withhold federal funding from cities with sanctuary policies have been blocked in court, and the legality of local non-cooperation has been repeatedly upheld. Still, the White House’s latest efforts represent an intensification, with DHS promising action "in most sanctuary cities across the country."
Adding to the tension, the U.S. Supreme Court on September 8, 2025, issued a 6-3 decision permitting federal agents in Southern California to conduct immigration raids that detain people based on race, ethnicity, language, or accent—even without "reasonable suspicion" that they are in the country illegally. This ruling is likely to embolden further enforcement efforts and fuel ongoing legal and political battles.
While DHS touts the success of recent operations—such as the 1,500 arrests in Massachusetts during Operation Patriot in May and 822 "criminal aliens" apprehended in Texas last month—critics argue that the real impact is fear and disruption in immigrant communities. As one Chicago resident put it, neighbors are "too afraid to open their doors." The coming weeks will likely see continued legal challenges, political posturing, and, most importantly, the lived consequences for families and neighborhoods caught in the crossfire.
For now, the nation’s sanctuary cities remain on high alert, bracing for further federal action and the uncertain road ahead.
