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Immigration

The U.S. Surveilled Left-Leaning Groups During Immigration Crackdown in Minnesota

Government agencies targeted protesters in two sweeping surveillance operations, new federal court filings show.

Immigration Enforcement Minnesota

Department of Homeland Security reports lay out plans to investigate “funding sources, organizational structures and predicate actions” for those organizations and others, over two dozen filings show, even before agents had identified any specific criminal basis to do so. Abbie Parr/AP Photo

By Manuela Silva

August 13, 2026 07:43 p.m.

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Homeland Security officials secretly spied on and investigated progressive groups and protesters during the Trump administration’s immigration crackdown in Minnesota earlier this year, new court filings show.

The motion for discovery, filed in the U.S.’s ongoing federal case against local activists, details two undercover surveillance operations that targeted protesters and dissidents during and following the Homeland Security Department’s January descent into the Twin Cities.

Through “Operation Puppet Master” and “Project Whipple Shield,” undercover agents attended community meetings across the capital region, covertly recorded conversations and obtained financial records — all without any basis for suspecting criminal activity. Attorneys who represent the 15 people charged with conspiring to impede or injure federal agents say the usage of such surveillance tactics on those practicing political dissent violated the First Amendment.

DHS officials conducted these operations under a directive President Donald Trump signed last September that tasked that agency and the Justice Department with investigating individuals and groups under an expanded definition of domestic terrorism.

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Operation Puppet Master was opened four days after federal immigration agents fatally shot Alex Pretti while he filmed officers detaining a woman. Associate Deputy Attorney General Aakash Singh used Trump’s September memo to encourage officials and prosecutors to pursue a sweeping set of cases that could generate headlines, The New York Times reported in March.

“Go big and go loud,” Singh said at the time.

One exhibit features a PowerPoint diagram of 18 organizations — including Twin Cities Democratic Socialists of America, Minnesota ICE Watch and labor union chapters like the AFL-CIO — that Homeland Security Investigations alleges were conspiring to interfere with the work of federal immigration agents in the state.

DHS reports lay out plans to investigate “funding sources, organizational structures and predicate actions” for those organizations and others, over two dozen filings show, even before agents had identified any specific criminal basis to do so.

Agents subpoenaed wire transfer information from the labor union SEIU and donation information from Voices for Racial Justice. Some tailed three of the defendants for a day in March. Others recorded panel discussions and team meetings to detail the ways protesters and dissidents planned to combat immigration officers stationed in the Twin Cities while evading breaking the law.

During a Sunrise Movement-Twin Cities meeting, one agent recorded possible actions members would take against immigration officers, including “shaming and bullying ICE” or “wasting ICE’s resources such as flooding their tipline and taking long time [sic] during interviews.” That agent embedded themselves in an operational planning group chat, a June investigation report details.

“These agents surreptitiously recorded dozens of conversations with ordinary people who were simply exercising their First Amendment right to protest ICE’s lawless rampage in our state,” Kevin Riach, the attorney who filed the motion for discovery, wrote. “The agents gathered information about Minnesotans from law enforcement databases and internet searches, and created dossiers that are apparently now available agency-wide.”

The documents, filed in U.S. District Court in Minnesota, are part of a broader request for more information regarding the investigation and the undercover agents who participated. In his motion for discovery, Riach asked the government for more relevant documents — including about an “Operation Keyhole” mentioned in an opening report, under which the first case was accepted — and internal agency communications.

Author

AJI-Fellow2025_Manuela Silva.png Manuela Silva is a reporter at The Washington Sun and an Allbritton Journalism Institute fellow.

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