People whistle and film as federal agents block an alley near 35th Street and Chicago Avenue while they break a car window to detain a man and his young daughter Thursday, Jan. 22, 2026. (Photo by Nicole Neri/Minnesota Reformer)

Less than an hour after the Saturday morning killing of Alex Pretti by federal agents in south Minneapolis, conservative influencer Cam Higby took to social media with a sensational claim: Higby had “infiltrated” the group chats fueling local resistance to Operation Metro Surge.

On Monday, FBI director Kash Patel said he had “opened an investigation” into the chats. Many are said to be hosted on Signal, the encrypted messaging app.

“You cannot create a scenario that illegally entraps and puts law enforcement in harm’s way,” Patel said in a podcast interview with Benny Johnson, another conservative influencer. Johnson’s title for the episode’s YouTube stream, “Kash Patel Announces FBI Crack-Down of Left-Wing Minnesota Terrorist Network LIVE: ‘Tim Walz Next…’,” left little to the imagination.

In response to emailed questions about the nature of its investigation, the FBI declined to comment. 

First Amendment lawyers and national security experts expressed deep skepticism that any charges stemming from it will stick, however. 

“As a general proposition, reporting on things you are observing and sharing those observations is absolutely legal,” Jane Kirtley, professor of media ethics and law at the University of Minnesota Law School, said in an interview.

A guide that Higby described as “the watered down opsec version” of a “TRAINING MANUAL for domestic terrorist patrols chasing ICE agents in Minneapolis” instructs observers to draw attention to suspected ICE activity using whistles and car horns — but specifically warns against impeding officers.

Kirtley said Patel’s statements to date have been too vague to support firm conclusions about what the FBI will actually investigate or what charges, if any, the United States Department of Justice would bring as a result. The sorts of loaded terms that influencers like Higby and President Trump himself have used to describe organizers’ activities — such as “conspiracy” or “insurrection” — are formal legal concepts that require certain standards to be met, she added.

Jason Marisam, a constitutional law professor at Mitchell Hamline School of Law, said any prosecution would likely need to pass a two-part test established in a nearly 60-year-old U.S. Supreme Court ruling, Brandenburg v. Ohio.

Brandenburg prohibits speech only if it is “directed to inciting or producing imminent lawless action,” such as violence against law enforcement officers, and “is likely to incite or produce such action,” according to a summary by Cornell Law School’s Legal Information Institute. 

Brandenburg is “a very high bar,” Marisam said. Speech that only indirectly led to “lawless action,” such as coordinating a protest that later turned violent, would likely not meet it, he added.

Marisam said Brandenburg, incidentally, is the same standard that former special counsel Jack Smith would have needed to meet had his January 6th prosecution against President Trump gone to trial, Marisam added. That case was mooted after Trump won a second term and subsequently oversaw a campaign of professional retribution against the career prosecutors on Smith’s team. 

Marisam said narrowing or overturning Brandenburg has not yet been a priority for conservatives in the judiciary, despite self-evident benefits for Trump’s efforts to quell dissent and consolidate power. But he acknowledged that the “politics of free speech” can change depending on who’s in charge in Washington.

For instance, Trump supporters castigated what they perceived to be limits on free speech during the Biden years, but have remained silent in the face of a student’s deportation for writing an op-ed. 

Still, Patel’s apparent interest in Twin Cities observers’ encrypted chats is likely less the opening move of a well-thought-out legal strategy than an effort to discourage legally permissible activity, Marisam said.

“It seems to me that (Patel’s) announcement is meant to chill speech ahead of time,” he said.

In a blog post published Tuesday, Patrick Eddington, a senior fellow with the libertarian Cato Institute, said federal prosecutors would likewise struggle to make hay out of Twin Cities observers’ use of the encrypted messaging apps themselves. 

Trump officials and right-wing pundits have pointed to Signal’s popularity within the observer networks as evidence that participants want to evade legal accountability for their actions. Signal uses end-to-end encryption, meaning messages sent on properly secured devices kept in their owners’ possession are effectively impossible for third parties to see. Signal itself can’t access messages or calls sent over the app, the company says, though messages on a user’s device can be read if it is hacked or stolen. (Or, if the wrong person is added to a Signal chat, as when senior national security figures in the Trump administration — including Secretary of Defense Pete Hegseth — sent information about military operations to the editor of The Atlantic magazine after he’d been accidentally included.) 

Eddington, who works on homeland security and civil liberties issues for Cato, said the Ninth Circuit Court of Appeals’ 1999 ruling in Bernstein v. United States Department of Justice established ordinary citizens’ rights to use encrypted channels for communication they wish to keep private. Government efforts to curtail encryption could impede individuals’ rights under the Fourth Amendment to the U.S. Constitution, which prohibits “unreasonable search and seizure.”

Eddington cited a much earlier precedent that may well have informed the Constitution’s privacy protections, though its contemporary legal relevance is unclear. Thomas Jefferson, James Madison and other members of America’s founding generation used “codes and ciphers” to communicate before, during and after the Revolutionary War, Eddington wrote. 

“The use of encryption to keep government authorities from getting access to our private communications is literally as American as apple pie,” he wrote.

Judge Hannah Dugan leaves court in her federal trial, where she was convicted of a felony for obstructing immigration officers. (Photo by Isiah Holmes/Wisconsin Examiner)

According to the Eastern District of Wisconsin’s Interim U.S. Attorney Brad Schimel, freshly appointed to his position by President Donald Trump, the federal trial of Milwaukee Judge Hannah Dugan had nothing to do with politics. “There’s not a political aspect to it,” Schimel told reporters after Dugan’s felony conviction on charges she obstructed U.S. immigration agents as they tried to make an arrest inside the Milwaukee courthouse. “We weren’t trying to make an example out of anyone,” Schimel said. “This was necessary to hold Judge Dugan accountable because of the actions she took.”

Schimel didn’t say whether Dugan’s very public arrest and perp walk through the courthouse was also necessary, along with the social media posts by Trump’s FBI director Kash Patel and Attorney General Pam Bondi, crowing about the arrest and sharing photos of Dugan in handcuffs. 

There is no doubt that the Dugan case was highly political from the start. 

As a coalition of democracy and civic organizations in Wisconsin declared in a statement after the verdict, Dugan’s prosecution threatens the integrity of our justice system and “sends a troubling message about the consequences faced by judges who act to protect due process in their courtrooms.”

But Schimel is right about one thing: Dugan’s trial this week was mainly about “a single day — a single bad day — in a public courthouse.”

That narrow focus helped the prosecution win a conviction in a confusing mixed verdict. The jury found Dugan not guilty of a misdemeanor offense for concealing Eduardo Flores-Ruiz, the defendant she led out a side door while immigration agents waited near the main door of her courtroom to arrest him. At the same time, the jury found Dugan guilty of the more serious charge of obstructing the agents in their effort to make the arrest. The two charges are based on some of the same elements, and Dugan’s defense attorneys are now asking that her conviction be overturned on that basis.

An observer watching the trial from afar with no inside knowledge of the defense strategy might wonder why Dugan’s defense team didn’t enter a guilty plea on the misdemeanor charge and then strongly contest the felony obstruction charge as an outrageous overreach in a heavily politicized prosecution. That might have led to a more favorable mixed verdict, in which the jury found that Dugan was probably guilty of something, but that it did not rise to the level of a felony with a potential penalty of five years in prison.

I’m no expert, but daily reports from the trial this week gave me the strong impression that things weren’t going well for Dugan as long as witnesses and lawyers focused on a blow-by-blow account of the events of April 18. Witness testimony described an agitated Dugan, whose colleague, Judge Kristela Cervera, testified — damagingly —  that she was uncomfortable with how Dugan managed the federal agents she was outraged to find hanging around outside her courtroom. 

It’s not surprising that the jury agreed with the prosecution that Dugan was not cooperative and that she wanted to get Flores-Ruiz out of her courtroom in a way that made an end-run around the unprecedented meddling of federal immigration enforcement inside the courthouse. Like other judges and courthouse staff, she was upset about the disruption caused by ICE agents stalking people who showed up to court.

But, as Dean Strang, a law professor at Loyola University Chicago School of Law and a long-time Wisconsin criminal defense lawyer, told me in April just before he joined the defense team and stopped talking about the case to the press, “Whatever you think of the actual conduct the complaint alleges, there is a real question about whether there’s even arguably any federal crime here.” 

The government’s behavior was “extraordinarily atypical” for a nonviolent, non-drug charge involving someone who is not a flight risk, Strang added.

The handcuffs, the public arrest at Dugan’s workplace, the media circus — none of it was normal, or justified. When Bondi and Patel began posting pictures of Dugan in handcuffs on social media to brag about it, “what is it they are trying to do?” Strang asked. His conclusion: “Humiliate and terrify, not just her but every other judge in the country.”

The Wisconsin Democracy Campaign, Voces de la Frontera, and Common Cause-Wisconsin agree with that assessment, writing in their statement reacting to the conviction that Dugan’s felony conviction threatens the integrity of our justice system as a whole, and undermines the functioning of the courts by scaring away defendants, witnesses and plaintiffs who are afraid they might be arrested if they show up to participate in legal proceedings.

But that big picture perspective was not a major feature of the defense’s closing arguments, which relied heavily on raising reasonable doubt about Dugan’s intentions and her actions during a stressful and chaotic day.

That’s frustrating because, contrary to Schimel’s assertions, the big picture, not the events of “a single bad day” is what was actually at stake in this case.

One of the most distressing aspects of the Dugan trial was the prosecution’s through-the-looking-glass invocation of the rule of law and the integrity of the courts.

The federal agents called to the stand, the prosecutors in the courtroom, and Schimel, in his summary of the case, made a big point about the “safety” of law enforcement officers. 

Repeatedly, we heard that immigration agents prefer to make arrests inside courthouses because they provide a “safe” environment in which to operate. 

In his comments on the verdict, Schimel emphasized that Dugan jeopardized the safety of federal officers by causing them to arrest Flores-Ruiz on the street instead of inside the courthouse: “The defendant’s actions provided an opportunity for a wanted subject to flee outside of that secure courthouse environment,” Schimel said.

This upside-down view of safety has become a regular MAGA talking point, with Republicans claiming that when citizens demand that masked agents identify themselves or make videos of ICE dragging people out of their cars, they are jeopardizing the safety of law enforcement officers — as opposed to trying to protect their neighbors’ safety in the face of violent attacks by anonymous thugs. 

Churches, day care centers and peaceful suburban neighborhoods are also “safe” environments for armed, masked federal agents. But their activities there are making our communities less safe. 

Assistant U.S. Attorney Kelly Brown Watzka, delivering the prosecution’s closing argument, told the jury it must draw a line against judges interfering with law enforcement, or else “there is only chaos,” and that “chaos is what the rule of law is intended to prevent.”

But chaos is what we have now, with federal agents terrorizing communities, dragging people out of courthouses and private residences, deporting them without due process and punishing those who stand in their way in an attempt to defend civil society.

The real questions raised by Dugan’s case are whether we believe the “safety” of the agents making those dubious arrests matters more than the safety of our communities, and whether we want the courts to be able to regulate the conduct in their own courthouses as a check on the government’s exercise of raw power.