The Grey Zone: When Do Protest Observers Become Lawbreaking Participants?

While Good’s shooting presents a distinct issue, her case and Lemon’s highlight the complex legal issues surrounding those who claim to be chronicling protests. Legal observers and journalists have long worked on the frontlines of civil unrest, the former documenting instances of alleged police misconduct in violation of constitutional rights to peaceably assemble, and the latter chronicling the assemblies. Their efforts have brought transparency and accountability. But what happens when legal observers and journalists act, or are seen by authorities as unlawful protestors rather than the neutral parties they are supposed to be? To what degree do their titles afford them special protections from prosecution in a court of law?

These questions have been brought into sharp relief as the Trump administration has brought hundreds of cases against people whom it alleges have not merely monitored but participated in illegal actions impacting immigration enforcement operations. 

“We respect the First Amendment and the right to peacefully protest,” a DOJ spokesperson told RealClearInvestigations, but “journalists and observers are not provided special protections to obstruct law enforcement operations.”

Northwestern University Law Professor Steven Lubet, who has criticized the Trump administration’s approach to immigration, concurred that legal observers “have no special legal status,” nor do journalists have “license to engage in violence or disruption.” But, he added, "law enforcement authorities should have a heavy burden to show that a journalist...or legal observer...had overstepped their role."

Although it did not respond to a request for comment, the American Civil Liberties Union has litigated against federal law enforcement authorities in connection with ICE’s activities in Minnesota. It argues that the government is violating the “constitutional rights” of people “observing, documenting, and protesting ICE activity in their neighborhoods.”

Like so many issues, the very nature of protest and the definitions of legal observers and journalists have come into question during the Trump years. America has a long history of protest, but the anti-ICE protests are different. Typically, protestors have engaged in somewhat organized demonstrations, with law enforcement responding if there is violence or property damage. But residents of Minneapolis, Los Angeles, and other sanctuary jurisdictions to which the second Trump administration has surged ICE agents have turned this dynamic on its head by arriving at the scene in response to law enforcement actions, and sometimes challenging such efforts.

It is hard to distinguish protestor from legal observer as many self-described ICE-watchers pursue officers in their cars and approach them during encounters – often times with phone in hand to record the events, and, they claim, to deter misconduct. Alex Pretti, an armed man who was killed by border patrol agents in Minneapolis after appearing to come to the assistance of another protestor, had been filming the scene before his deadly encounter. While he was widely described as a legal observer, just a few days prior, he had kicked in the taillight of an ICE vehicle, raising the murky issue of whether one can toggle back and forth between protester and observer depending on the circumstances.

The fine line between participant and observer also emerged during the Kyle Rittenhouse murder case. Rittenhouse shot three people, two fatally, during the Black Lives Matter unrest in Kenosha, Wisconsin, in August 2020. The lone survivor, Gaige Grosskreutz, testified that he had pointed his gun at Rittenhouse, leading the then-17-year-old to shoot in apparent self-defense – a turning point in the trial leading to Rittenhouse’s acquittal. Grosskreutz was operating not only as a paramedic when the incident occurred, but also as an ACLU legal observer.

The decline of traditional news outlets has also muddied the waters, giving rise to the concept of citizen journalists. Given his long career at CNN, Lemon, who works independently, may qualify as a journalist – though the government alleges he was not just reporting on but participating in the church disruption. The question, however, can be harder to answer when it involves bloggers and those who post news on social media. Similarly, where journalists have long been constrained by the fear of being fired for violating professional standards of neutrality, such guardrails have been weakened in the new, highly politicized media landscape.  

As growing numbers of Americans have vowed to ramp up resistance to President Trump’s policies, and the administration seems committed to arresting what it deems unlawful actors, these definitions may take on added significance. Judges and juries will have to weigh First Amendment-protected activities against law enforcement imperatives and make judgment calls about where to draw the line based on the facts and evidence in each case. So too will prosecutors, often operating in Democrat-dominated jurisdictions, who must weigh these competing claims.

Black Panthers and the Constitution

Legal observers exist to help vindicate the First Amendment rights of the assembled. According to the National Lawyers Guild, which formalized the practice, such observers “create documentation during events which can later be use (sic) in defense cases, public statements, and litigation which aims to hold law enforcement agencies accountable for the actions of their officers.” 

The Guild notes that legal observation has its roots in the Black Panthers’ “cop watch” activities of the late 1960s, whereby that militant organization “conducted armed citizens’ patrols in order to monitor the behavior of law enforcement officers in the Oakland Police Department.”

In 1968, in connection with anti-war and racial justice demonstrations in New York City, the Guild “took components from this practice” of cop watch to develop its legal observer program – the self-described “eyes and ears” of a larger infrastructure of “arrest hotlines, jail support teams, community bail funds ... attorney referral networks, and more.”

Those who have adopted the Guild’s practice, such as the Minnesota ICE Watch group with which Good was reportedly affiliated, have advocated for activities that blur the line between observation and participation in protests. They defend their actions as a response to ICE agents who, they claim, routinely use excessive force, including in the killings of Good and Pretti.

According to its social media postings, Minnesota ICE Watch exists not only for the purpose of “documenting” and “archiving” but “resisting … ICE, Police and all Colonial Militarized Regimes.” 

Minnesota ICE Watch’s Instagram account shows the group has disseminated materials detailing how to share intelligence about agents’ movements and tipping off illegal aliens to impending raids. They also advise taking “direct action” against authorities to prevent such a “kidnapping,” including harboring those being pursued in one’s car or a “lockable room.” 

Likewise, according to a City Journal review of trainings and communications of “Defend the 612,” a prominent organizer of anti-ICE activities, including ICE watch trainings in Minnesota, “members and related officials have encouraged protesters to impede law enforcement; pushed civilians toward legally and physically risky confrontations; and helped mobilize a counterprotest that turned violent.” 

Blurry Lines

Some anti-ICE groups, as well as the Guild and the ACLU, warn activists that there is a line between protected behavior and that which might run afoul of the law, and that observers may sometimes become liable as actors. 

The Guild warns that law enforcement may smudge that line. “Just because you have legal rights does not mean the government will respect them. In fact, law enforcement will generally trample over your rights,” its “Know Your Risks” pamphlet reads. 

Leigh Ann O’Neill, the chief legal affairs officer of the conservative America First Policy Institute, told RCI that “Observing…officials in public is generally lawful, but conduct that harasses, intimidates, doxxes, obstructs, or aids evasion of lawful enforcement can trigger criminal liability.” 

For its part, DOJ has slapped some 650-plus individuals with charges under federal law since the summer of 2025, according to a recent Reuters analysis – including for allegedly following federal agents in their cars. In some instances, media reports suggest that prosecutors have downgraded such charges or chosen not to prosecute.

In Minnesota, prosecutors have reduced charges from felonies to misdemeanors or dismissed them in 20 cases pertaining to alleged attacks on law enforcement. In cities such as Chicago and Los Angeles, prosecutors have similarly found some of their cases dismissed or unsuccessful due to a lack of sufficient evidence or from overcharging defendants, judges have suggested. A Wall Street Journal analysis suggests similar trends regarding cases in which defendants were accused publicly of assaulting federal officers.

Arrests and Lawsuits

In response to media scrutiny suggesting an overzealousness in pursuing such cases, outgoing Department of Homeland Security Director Kristi Noem reported that vehicular attacks, death threats, and assaults against ICE agents increased dramatically from when Trump took office to the end of 2025. DHS officials reported 275 assaults as compared to the 19 reported assaults during the same period in 2024.

Meanwhile, in a counter-offensive against the immigration cops, the ACLU, TNG-NCWA, and dozens of individuals, including self-described observers and journalists, have filed suit in Minnesota against the Trump administration, claiming federal agents violated their rights during “Operation Metro Surge” and in analogous operations in cities across the country. “[O]bservers and protesters have been met with gratuitous uses of force, threats, detention, and intimidation ... all in an attempt to chill, discourage, prevent, and retaliate against protesters and observers from exercising their First Amendment rights,” the plaintiffs allege.

Amid an outcry from Democratic officials and anti-ICE activists over outgoing Homeland Security Secretary Kristi Noem’s casting of Good’s conduct as “domestic terrorism,” Deputy Attorney General Todd Blanche said in January that the department would not be investigating Good’s killing.

Conversely, shortly after the shooting of Pretti, the Justice Department opened a civil rights investigation into the incident.

While opponents of the Trump administration’s mass deportation policy try to halt it, Attorney General Pam Bondi and FBI Director Kash Patel have indicated the bureau is probing the networks behind anti-ICE activism.

Journalism or Activism?

Although reporters have a well-established constitutional right to gather the news, they cannot break the law to do so.

“Journalists have no special exemption from generally applicable laws if they trespass, interfere with someone’s right to worship, or otherwise engage in illegal activity,” O’Neill said. Many journalists, for example, have been jailed for refusing to identify anonymous sources of classified material.

In Don Lemon’s case, the government alleges that he – and 38 others – conspired to and violated the rights of worshippers at St. Paul’s Cities Church to freely practice their religion. Prosecutors allege in their indictment that Lemon did not act exclusively as an independent journalist but as a co-conspirator in an illicit operation. Among other things, they claim that he “took steps to maintain operational secrecy” when livestreaming in advance of what Lemon described as the “resistance” action; hounded the pastor with questions “to promote the operation’s message;” ignored the pastor’s request to leave the church; and stood at the church’s main door “where he confronted some congregants and physically obstructed them as they tried to exit…”

Lemon said in a statement that he was arrested “for doing what I have been doing for 30 years. The First Amendment to the U.S. Constitution protects that work for me and countless other journalists who do what I do. I stand with all of them, and I will not be silenced. I look forward to my day in court.”

While accepting a Samizdat Prize last month from the RealClearFoundation – which supports RCI – for his work defending free speech, Harvard law professor Alan Dershowitz argued that Lemon “helped promote the cause of journalism.”

“Now, he may have gone beyond journalism. He may have blocked entrances. He may have done things that don’t deserve journalism,” Dershowitz said. “But to the extent you have any doubts, they should always be resolved in favor of the First Amendment and in favor of journalism.”

Unequal Justice?

Just as supporters of Lemon believe that Trump officials are targeting journalists they see as liberal – with AG Bondi ordering agents to arrest Lemon, and three others – some say prosecutors under the Biden administration went after reporters it considered ideological foes. William Shipley, a former federal prosecutor turned criminal defender who represented some 90 defendants connected to the January 6 riots in Washington, D.C., said one of his clients, conservative freelance journalist Steve Baker, was at the Capitol capturing footage that would be licensed to several outlets subsequently. Chasing the story, he entered the Capitol during the riot.

Several years later, Baker was charged with four nonviolent misdemeanor counts, including trespassing and disorderly conduct, for which he was arrested.

Shipley would argue in court that he had identified some 60 other journalists who had done some or all of the same things Baker did that day, but went unprosecuted.

The government “singled out conservative members of the press and used commentary by them either recorded in real time, or things they reported later, to show ‘support’ for the rioters and then prosecuted them based in part on that commentary,” Shipley said. 

“At the same time, left-wing reporters who did the exact same acts were not prosecuted and won awards for their ‘coverage’ because they expressed condemnation of the rioters.”

Baker would plead guilty to charges shortly after the 2024 election, only to be pardoned by President Donald Trump several weeks later.

Filmmaker Georgia Fort was charged as a co-conspirator alongside Lemon in the Cities Church disturbance. She said following her release from jail that “As a journalist who has worked in media for more than 17 years, I leave this federal courthouse today with one question, ‘Do we have a Constitution’?”

Lawyers for Lemon and Fort, in a joint filing, asserted that they were each present at Cities Church “in their capacities as journalists.” “At no point did either engage in chanting or other behavior characteristic of protesting or activism,” they represented to the court.

Lemon has publicly said he didn’t enter the church with the protestors and didn’t impede or intimidate anyone. “They said that I peppered people with questions. That’s what reporters do,” he argued.

Meanwhile, despite ICE having decamped from the Twin Cities, the administration’s opponents are ramping up for more activism.

In February, the No Kings movement launched a series of trainings nationwide as part of its “Eyes on ICE” monitoring program – a precursor to what the group is billing as the “largest nonviolent protest in American history” on March 28th.

“When the Trump administration sends mass militia to terrorize neighborhoods, retaliates against people who protest, or uses federal power to punish those who speak out, it sends a clear message: to stay silent or to pay the price,” the emcee to one such training session, progressive activist Ash-Lee Woodard Henderson said.

Documenting and recording ICE agents while carrying out their duties, she and those who followed her argued, would be a critical tool to “resist” such “occupying” forces.

Meanwhile, Congress remains at an impasse over immigration enforcement, with Democrats seeking to impose significant restraints on ICE, while Republicans seek to curtail sanctuary policies – and potentially dramatically increase the penalties for interfering with ICE officers.