During federal immigration enforcement operations in Chicago's Little Village neighborhood on October 23, 2025, federal agents led by U.S. Border Patrol Commander-at-Large Gregory Bovino detained at least five people, including two Benito Juarez Community Academy high school students and at least one U.S. citizen. A 16-year-old junior was detained and later released; video showed federal agents grabbing a teenage boy from a sidewalk and forcibly handcuffing him. When dozens of residents and protesters gathered near a discount mall at 27th and Whipple streets to oppose the enforcement action, federal agents wearing military-style camouflage and gas masks deployed tear gas and pepper spray into the crowd. Video evidence shows Bovino himself tossing a tear gas canister into the crowd after being told not to do so by Little Village Community Council President Baltazar Enriquez. A 24-year-old U.S. citizen woman protesting was also detained and placed in a van; her sister reported not hearing from her as of Thursday afternoon. Attorneys filed a federal complaint alleging agents violated a court order prohibiting riot control weapons without imminent threat and requiring prior warnings. U.S. District Judge Sara Ellis ordered Bovino to testify for five hours and appear in person for a status hearing.