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John McCormack /

Fear and Loathing in Chicago

What is the Trump administration’s endgame in the Windy City?
Residents and protesters clash with federal agents in the East Side neighborhood of Chicago on October 14, 2025. (Photo by Joshua Lott/The Washington Post via Getty Images)

CHICAGO—The Department of Homeland Security announced on September 8 it was starting to “target the worst of the worst criminal illegal aliens in Chicago” in a stepped-up campaign of immigration enforcement the Trump administration had dubbed “Operation Midway Blitz.” 

Hearing those two words together—Midway and Blitz—is more than a bit odd to anyone with a passing familiarity with World War II: Midway was the turning-point battle for the Americans in the Pacific, and Blitzkrieg was the German word for the Wehrmacht’s style of “lightning war.” Midway is, of course, also the name of the airport in southwest Chicago, near heavily Latino neighborhoods where Immigration and Customs Enforcement (ICE) agents have targeted operations.

John McCormack is a senior editor at The Dispatch and is based in Washington, D.C. Prior to joining the company in 2023, he was Washington correspondent at National Review and a senior writer at The Weekly Standard. When John is not reporting on politics and policy, he is probably enjoying life with his wife and daughters in northern Virginia or having fun visiting family in Wisconsin.

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