HSI Testimony Reveals Minnesota Company Funds Undercover Operations as Minnesota 15 Case Draws Scrutiny
HSI supervisor Joshua Brenner testified Oct. 20 that Midwest Transfer Companies LLC, registered in Bloomington since 2010, helps fund operations under Operation Keyhole, a federal funding program dating to 2008. Brenner said the company does not fund Operation Puppet Master, the undercover effort at the center of the Minnesota 15 case, which opened in the middle of Operation Metro Surge. Defense attorneys questioned why a government agency would operate through a private LLC, and one compared HSI’s role to COINTELPRO, the FBI program that targeted Black organizers and civil rights leaders. The hearing also revealed a flawed ICE memo targeting a federal defender, prompting an apology from the judge. Prosecutors filed a superseding indictment Oct. 22. The defendants have not been convicted.
A Homeland Security Investigations supervisor testified in federal court in Minneapolis that the agency uses a Minnesota company to fund some of its undercover operations, the clearest public look yet at the financial machinery behind the federal surveillance at the center of the Minnesota 15 case.
Joshua Brenner, an assistant special agent in charge with HSI, testified Oct. 20 that a company called Midwest Transfer helps fund operations under Operation Keyhole. A defense attorney in the case confirmed to MSR that the company is Midwest Transfer Companies LLC.
Minnesota Secretary of State records show Midwest Transfer Companies LLC was registered Oct. 6, 2010, and remains active and in good standing, with an office address in Bloomington. The records do not identify any connection to the federal government. The Secretary of State’s office did not respond to questions about the company by an Oct. 23 deadline.
“Why would they set up an LLC unless they’re trying to do things that they wouldn’t be allowed to as a government agency?” said Jordan Kushner, who represents defendant Erik Davis, a Macalester College professor. “It’s certainly controversial when the CIA does it, when they’re doing shady operations in foreign countries. But it’s a new level now when they’re using those sorts of tactics on the American public.”
In a Sept. 10 court brief, the Justice Department described Operation Keyhole as a funding and administrative program dating to 2008, separate from individual investigations. It said Operation Puppet Master and Project Whipple Shield used that support, and argued that disclosing unrelated investigative material could endanger agents and other cases. Brenner testified that Midwest Transfer does not fund Puppet Master or Whipple Shield.
An HSI case-opening report, filed by the defense Aug. 13, describes Operation Puppet Master as an effort to investigate support for violence and interference with federal officers. It documents placing undercover agents into groups identified as potential threats and says HSI is conducting a financial investigation. The report lists Jan. 28 as the opening date and Feb. 16 as its approval date. That timeline places the operation’s start in the middle of Operation Metro Surge.
Federal agents arrested about 3,800 people in Minnesota between Dec. 1, 2025, and March 10, and less than a quarter of them were convicted criminals, according to a CBS News analysis of data obtained by the Deportation Data Project. Despite the White House targeting people of Somali descent, they accounted for less than 3% of arrests.
Kevin Riach, who represents defendant Isaac Sant, compared HSI’s role to COINTELPRO in remarks published by WIRED on Oct. 28. COINTELPRO was the FBI program that targeted civil rights leaders and Black organizers from the 1950s through the 1970s.
The hearing also drew scrutiny of a memo by ICE Deportation Officer Michael J. O’Neal, which accused Assistant Federal Defender Matthew Deates of helping his client, Ezequiel Portillo Rodriguez, avoid arrest. Prosecutors accidentally turned the memo over to defense lawyers as discovery.
The memo contained several errors. It said the hearing took place before Chief Magistrate Judge Raymond Erickson, who has since retired from the U.S. District Court for the District of Minnesota. O’Neal also acknowledged he did not know a federal court in California had barred the arrest he was trying to make. Deates denied in a sworn declaration that he overheard O’Neal’s conversation with a deputy U.S. marshal.
Asked whether the government had evidence that Deates committed a crime, Assistant U.S. Attorney Tory Sailer said no. Sailer said the memo’s release “was an oversight by our office,” and added that Deates is not under investigation.
Magistrate Judge David Schultz apologized to Deates from the bench and ordered the memo destroyed.
“I think it’s outrageous that agents of the United States government would follow a federal defender who is actually in the act of making sure that his client complies with a court order,” Schultz said.
Riach said the episode raised broader questions about the agency’s credibility.
“The agents don’t even know the names of who they’re talking to,” he said. “It’s like an endless fountain of impeachment material.”
Prosecutors filed a superseding indictment against the 15 defendants Oct. 22. Count One charges all 15 with conspiracy to impede or injure a federal officer; the other counts charge individual defendants with offenses including solicitation, interstate threats, interstate stalking and assaulting a federal officer. The charges are allegations, and the defendants have not been convicted.
The Justice Department and U.S. Immigration and Customs Enforcement did not respond to requests for comment by an Oct. 23 deadline.
Clint Combs is a freelance journalist and contributing writer for the Minnesota Spokesman-Recorder. He welcomes reader responses at combs0284@gmail.com.