“I cannot recall anything like this . . . I've been defending First Amendment rights since 2006, and this is the most serious of threats I can recall.” — Will Creeley
This is the sixth installment of “Executive Watch” by Professor Timothy Zick. Central to this post is a core First Amendment principle — namely, that the government ought not use its power in the service of revenge. By the same token, such power should never be exercised to attack those who hold opposing views. Seen in that light, the First Amendment was designed to place principle above punishment, while stationing the very thought of revenge outside the purview of constitutional legitimacy. In free speech terms, evenhandedness is the operative norm. That norm, grounded in part in fundamental notions of due process fairness, is defied when, as Jameel Jafffer has noted, the Trump “administration . . . retaliate[s] against lawyers” who litigate cases against Trump or his policies.
Such abuses of power are tantamount to blackletter constitutional violations. As Justice David Souter put it in Hartman v. Moore, “[T]he law is settled that as a general matter the First Amendment prohibits government officials from subjecting an individual to retaliatory actions, including criminal prosecutions, for speaking out.”
Against that backdrop comes this installment of “Executive Watch,” on how the Trump administration has waged war against those who have opposed him, along with those who hold views he dislikes.
The various posts of “Executive Watch” inform a forthcoming book by Professor Zick, which will be published by law publisher Carolina Academic Press and will be in print by mid-December or thereabouts.
Donald Trump made this ominous campaign pronouncement to his supporters during the run-up to the 2024 presidential election. During the early part of his second term, Trump and his administration have followed through with a vengeance. In the months since his inauguration, he and agencies acting at his direction have taken a wide variety of official actions intended as payback for political, cultural, and other grievances.
Professor Timothy Zick
Indeed, retribution has been one of the most consistent early through lines of Trump 2.0. The president has taken actions intended to exact revenge on current and former government officials, law firms, nonprofits, broadcasters, businesses, and universities.
The First Amendment prohibits the government from retaliating against individuals based on their protected expression. In the preliminary stages of litigation, courts in a variety of contexts have enjoined Trump administration orders and actions on this ground. First Amendment retaliation claims have been a critical and, so far, successful first line of defense against Trump 2.0’s retribution and grievance campaign.
As in other areas, however, lawsuits and legal claims alone will not prevent this administration from chilling the protected expression of its perceived enemies.
Trump’s retribution campaign
The Trump administration’s retribution campaign has taken various forms. There have been some petty acts. For example, the Defense Department removed the photo of General Mark Milley, who publicly broke with Trump over his response to the Black Lives Matter demonstrations. However, many other executive actions against critics and political opponents carry much more serious consequences. For instance, Trump ordered that the security clearances and security details of former officials who have openly criticized him be cancelled — in some instances, even in the face of credible threats to the person’s life.
Although he vowed in an executive order to depoliticize the Justice Department, Trump has directed the termination of federal prosecutors and Federal Bureau of Investigation employees who participated in criminal investigations relating to the Jan. 6, 2021 attack on the U.S. Capitol. The Trump Justice Department has also threatened to open or initiate criminal investigations against past and current public officials, including former FBI Director James Comey and Representative Alexandria Ocasio-Cortez, who have criticized Trump or the administration. The Justice Department recently indicted a sitting congresswoman involved in a protest at an immigrant detention center. And it has reportedly opened a criminal investigation into statements by former New York Governor Andrew Cuomo about the COVID-19 pandemic. Finally, Trump recently suggested arresting California Governor Gavin Newsom. His “primary crime,” according to Trump, was “running for governor.”
Trump has targeted individuals who served in his first administration. He issued executive orders that target former officials for public statements they made about the 2020 presidential election and criticisms of the first Trump administration. One of the orders directs the attorney general to open a criminal investigation, while the other accuses the target of violating the Espionage Act — a crime that carries a potential penalty of death. After legendary rock star Bruce Springsteen made comments at his concerts critical of the Trump administration, the president threatened on Truth Social to open a “major investigation” into whether his endorsement of Kamala Harris violated federal campaign finance laws.
Trump has also issued several executive orders targeting law firms based on their past representation of clients. Among other things, those orders purport to strip lawyers of security clearances, bar them from federal buildings, and interfere with their representation of federal contractors — in short, to destroy their businesses. The Trump administration also terminated federal grants to the American Bar Association, based on the ABA’s litigation against the administration and the group’s criticism of various Trump administration policies.
The administration has also targeted American universities, or at least those it considers to be bastions of liberal advocacy and influence. Its campaign against Harvard University consists of at least eight separate federal agency investigations. These investigations are predicated primarily on claims that Harvard has engaged in “Diversity, Equity, and Inclusion” (DEI) and failed to protect Jewish students from unlawful forms of discrimination during campus demonstrations. The investigations have so far led to the denial of billions of dollars in federal research and other funding, a ban (currently subject to a restraining order) on admitting any international students, and a threat to revoke the university’s tax-exempt status. As part of its enforcement actions against the university, the Trump administration has issued lists of demands to Harvard concerning everything from its admissions policies to oversight of specific academic departments.
Harvard University is not alone. Other major universities, including Brown University, Princeton University, Columbia University, and the University of Pennsylvania, have also been subject to or threatened with Trump administration investigations. Unlike Harvard, these institutions have not filed lawsuits defending their First Amendment and academic freedom rights. Perhaps as a result, the administration has not used the full panoply of agency investigations and demands it has brought to bear against Harvard. The administration has put many other universities on notice that they, too, are subject to civil rights and other investigations for DEI, anti-Semitism, and other purported offenses. Even some graduate school programs have been targeted. A prosecutor in the Trump administration informed Georgetown University Law Center that it risked federal funding denials and other consequences — including a ban on internships for its students in the D.C. prosecutor’s office — if the law school incorporated DEI into classroom instruction or otherwise supported DEI.
Trump has also sought to terminate funding for public broadcasting stations. The president issued an executive order, “Ending Taxpayer Subsidization of Biased Media.” The order directs the termination of all federal funding for the Public Broadcast Service and National Public Radio. The president made clear in the text of the order that it was issued because, in his view, the stations’ news and other programming was “biased.”
Finally, the Trump administration has also gone after pro-Palestine campus protesters. Indeed, this effort has been a key part of the administration’s crackdown on aliens. The administration’s initial focus in its “mass deportation” campaign was not on raiding farms, schools, and businesses. Rather, the Department of State and the Department of Homeland Security focused first on detaining and threatening to deport international students who engaged in pro-Palestinian political expression. Most of the targeted students participated in campus protests relating to the Hamas-Israel war — one of many issues that divided Americans during the 2024 presidential election, and one which then-candidate Trump spoke often about on the campaign trail.
First Amendment retaliation claims
Across this wide spectrum of administrative actions, plaintiffs have claimed in complaints and habeas corpus petitions that the administration has targeted them based on protected expression. In the preliminary rounds of litigation, several courts have enjoined administration actions and released detained students on this basis.
As the Supreme Court has held, the First Amendment bars governments from punishing speakers for engaging in protected expressive activity. This limit on government action is so deeply ingrained in First Amendment jurisprudence that it is part of a longstanding and well-defined doctrine. To prevail in a First Amendment retaliation claim, a speaker must typically demonstrate: (1) they “engaged in conduct protected under the First Amendment”; (2) defendants “took some retaliatory action sufficient to deter a person of ordinary firmness in plaintiff's position from speaking again”; and (3) there is “a causal link between the protected First Amendment activity and the adverse action taken against” the speaker.
The targets of the Trump administration’s retribution campaign have all clearly been engaged in protected expression. The administration cannot plausibly claim that representing clients, filing lawsuits against the federal government, supporting DEI, engaging in protests, or criticizing government policies are outside the protection of the First Amendment. Indeed, these forms of expression lie at the First Amendment’s core.
Further, the government’s actions would certainly deter a “person of ordinary firmness” from speaking out. The targets of the Administration’s retribution campaign have faced the loss of billions of dollars, the potential destruction of businesses, the burdens of criminal investigation and prosecution, and imprisonment. Speakers of “ordinary firmness” subjected to these harms would naturally be reluctant to further antagonize Trump or his administration. Indeed, evidence that many law firms, universities, and others have capitulated to the Trump administration’s demands despite their dubious legal basis supports this argument. As Trump has shown time and again, by virtue of his office, the president can invoke the authority of a vast and powerful federal bureaucracy capable of inflicting financial and other harm on its targets.
The protected expression must also be a but-for cause of, and a motivating factor in, the government’s retaliatory action. The “causal connection” requirement has likewise posed little barrier to successful claims of retaliation brought against the Trump administration. In many instances, Trump and administration officials have rendered the connection explicit by relying on the representation of specific clients, the publication of op-eds, or litigation against the administration as a basis for the adverse governmental action.
To be sure, a retaliatory motive can sometimes be difficult to demonstrate. In lawsuits, Trump and officials in his administration have argued that their actions are valid attempts to enforce the nation’s civil rights, intelligence, immigration, and other laws against law firms, universities, federal grant recipients, and international students. In general, government defendants have argued that their focus is on unlawful activity, not protected speech.
The administration has had difficulty prevailing on this argument for two primary reasons. First, to establish retaliatory motive or purpose, courts have permitted plaintiffs to rely, among other things, on defendants’ contemporaneous statements. As noted, Trump and administration officials have done little to conceal their retaliatory intent. Some of the president’s executive orders make plain that they were issued because of the protected expression of targets. Further, the president and administration officials have provided bountiful additional evidence of a retaliatory motive.
Consider the executive order directing the defunding of PBS and NPR. Prior to issuance of the executive order, on his Truth Social account, the president posted:
“REPUBLICANS MUST DEFUND AND TOTALLY DISASSOCIATE THEMSELVES FROM NPR & PBS, THE RADICAL LEFT ‘MONSTERS’ THAT SO BADLY HURT OUR COUNTRY!”
The White House also published a statement alleging that PBS has “spread radical, woke propaganda disguised as ‘news,’” including the production of a documentary “making the case for reparations.”
In social media and other public statements, Trump has frequently suggested arresting or investigating his political opponents based on their viewpoints. In an Oval Office interview with Fox News host Sean Hannity, referring to law firms and other targets of his executive orders, Trump said:
“I went through four years of hell by this scum that we had to deal with. I went through four years of hell. I spent millions of dollars on legal fees and I won, but I did it the hard way. It’s really hard to say that they shouldn’t have to go through it also. It is very hard to say that.”
Trump also indicated at a news conference that while Columbia University, which decided not to challenge the administration, was no longer on “the hot seat,” by contrast “Harvard wants to fight, they want to show how smart they are, and they’re getting their ass kicked.”
Regarding the detention and deportation of international students, as a presidential candidate, Trump bragged that he would “crush” the pro-Palestine movement and deport student demonstrators based on their expression. These and other statements make explicit the administration’s retaliatory motive and the connection between protected speech and official retribution.
The second reason courts have rejected the administration’s proper motive arguments is that officials have failed to provide any non-retaliatory reasons for the actions they have taken. For example, one district court enjoined the Justice Department from terminating grants to the American Bar Association because it concluded the agency’s justifications were entirelypretextual. It concluded that “the government has not identified any nonretaliatory DOJ priorities, much less explained why they were suddenly deemed inconsistent with the goals of the affected grants. And the government’s different treatment of other grantees suggests this justification is pretextual.”
Likewise, in proceedings involving the detention and possible deportation of international students, courts have concluded that the government lacks any non-retaliatory justification for its actions — despite being afforded, in case after case, ample opportunity to provide one.
There will be cases in which retaliatory motive will be more difficult for plaintiffs to demonstrate, however. For instance, Harvard University would seem to have a strong claim that it has been singled out for protected expressive activity. But to succeed on its First Amendment retaliation claims, the university will have to convince courts that the administration has instituted actions against it in retaliation for protected speech, its exercise of academic freedom, or its decision to litigate against the administration. Despite the president’s public comments about Harvard, courts may conclude the Administration has presented sufficient evidence of non-retaliatory purposes — including enforcement of federal education and immigration laws.
For those who think this unlikely, it is well to remember that despite Trump’s many public derogatory statements about Muslims and Islam during his first term, the Supreme Court ultimately rejected First Amendment and other challenges to his first travel ban.
The insufficiency of retaliation-based injunctions
Although speakers have a right not to be retaliated against for engaging in protected expression, the First Amendment is not a guarantee against this harm. Along with many other commentators, I have observed that the judicial branch can offer necessary but ultimately insufficient protections for political and other expression.
In the First Amendment context, as in others, courts have provided some preliminary protection against abuses of executive power. But not all targets of retaliation will defend themselves. For example, many law firms and some prominent universities have entered “deals” or settlements with the administration rather than contest its actions in court. Even if they have strong First Amendment retaliation claims, others are likely to do the same. Making an example of Jenner & Block or Harvard University may be all that is necessary to chill otherwise protected expression by other institutions. Once they make a deal with the administration, it will be difficult or perhaps impossible for these entities to claim their expression was suppressed owing to governmental retaliation.
At this point several federal courts have admonished the administration that the First Amendment prohibits retaliatory actions based on protected expression. For most administrations, a string of judicial injunctions and strong rebukes from federal judges (appointed by presidents from both sides of the political aisle) would be a strong deterrent against future retaliatory measures. However, this administration plays by a different set of norms and rules.
Consider the fact that the administration has chosen not to appeal any of the decisions striking down its retaliatory measures against prominent law firms. As law professor W. Bradley Wendell told Adam Liptak of TheNew York Times:
They knew that these were losing positions from the beginning and were not actually hoping to win in court, but rather to intimidate firms into settling, as many firms did [.] Now that they have racked up the four losses in district courts, it is not surprising that they are not appealing, because I don’t think they ever thought these were serious positions.
As I observed in a prior post, anticipatory compliance or acquiescence allows the Administration to achieve otherwise unlawful objectives — including chilling expression through retaliatory measures. The administration has calculated that rather than risk being the target of an executive order or agency investigation, speakers or institutions will change their messaging, choose different clients, or tamp down their opposition to the administration. As Yale law professor Harold Koh told Adam Liptak:
The Trump administration probably feels like it has already succeeded beyond its wildest dreams [.] It never expected such capitulation. Through blatantly unconstitutional actions, it extracted deals from nine leading law firms for approaching $1 billion in coerced pro bono legal services and has chilled litigation and public opposition from law firms nationwide.
Even those who decide to challenge the administration and ultimately succeed will still face significant financial and other burdens. Law firms that fight the administration could end up losing clients. It may take decades for Harvard University to recover from the financial harm the Trump administration has inflicted upon it. And international students who prevail on First Amendment retaliation claims may discover that they still face deportation on other (possibly pretextual) grounds.
Successful First Amendment retaliation claims can liberate individual speakers from an invidious form of governmental retribution. However, in most cases these claims cannot prevent or reverse non-expressive damages or harms. And, as we have seen, when a presidential administration is committed to retribution against political opponents and does not care about case outcomes, the basic principle that the government cannot retaliate against speakers based on protected expression may be substantially under-enforced.
No rest for Mike Lindell after jury verdict in defamation case
Mike Lindell, CEO of My Pillow, stands outside the West Wing of the White House in Washington, U.S., January 15, 2021. REUTERS/Erin Scott/File Photo
A federal jury in Colorado on Monday found that one of the nation’s most prominent election conspiracy theorists, MyPillow founder Mike Lindell, defamed a former employee of a leading voting equipment company after the 2020 presidential election.
The jury found that two of Lindell’s statements about Eric Coomer, the former security and product strategy director at Denver-based Dominion Voting Systems, including calling him a traitor, were defamatory. It ordered Lindell and his online media platform, formerly known as Frankspeech, to pay Coomer $2.3 million in damages, far less than the $62.7 million Coomer had asked for to help send a message to discourage attacks on election workers.
“This is hurting democracy. This is misinformation. It’s not been vetted and it needs to stop,” Charles Cain, one of Coomer’s attorneys, told jurors in closing arguments Friday.
Lindell said he would appeal the financial award, saying Coomer’s lawyers did not prove Coomer had been harmed. He also said he would continue to speak out about election security, including criticizing the makers of election equipment like Dominion.
“I will not stop talking until we don’t have voting machines in this country,” said Lindell, who backs paper ballots counted by hand.
An anti-Trump statue has popped up on the National Mall in Washington. (Maxine Wallace/The Washington Post)
[A] work called “Dictator Approved,” an 8-foot-tall sculpture showing a gold-painted hand with a distinctive thumbs-up squashing the sea foam green crown of the Statue of Liberty [and] sits at the same location on the Mall near Third Street NW . . .
The artwork’s creators intended “Dictator Approved” as a rejoinder to the June 14 military parade and authoritarianism, according to a permit issued by the National Park Service. The parade, the creators wrote in the application, “[w]ill feature imagery similar to autocratic, oppressive regimes, i.e., N. Korea, Russia, and China, marching through DC.” The purpose of the statue, they continued, is to call attention to “the praising these types of oppressive leaders have given Donald Trump.”
University of Oregon insurer ordered to pay $200K in censorship case
In a resounding victory for First Amendment rights, Judge John V. Acosta awarded $191,000 in attorney fees to the legal team of Institute for Free Speech client Professor Bruce Gilley yesterday. The fee award follows the March 2025 settlement in which the university acknowledged that Gilley’s speech should not have been censored and agreed to implement significant pro-speech reforms.
The awarded fees will be paid by the school’s insurer, United Educators, with $147,070 to be paid to the Institute for Free Speech and $43,930 to be paid to the Angus Lee Law Firm. The fees, combined with the more than $533,000 the university had already paid its own attorneys by November 2024, bring the total public cost of defending the university’s unconstitutional censorship to at least $724,000.
Plaintiff Bruce Gilley and local counsel Angus Lee
These costs of almost three-quarters of a million dollars all ultimately stem from the university’s stubborn defense of DEI officials blocking Gilley for simply posting “all men are created equal.” This figure also doesn’t include billing after last November, the full scope of which would push the cost higher.
“This fee award reflects the substantial resources required to vindicate fundamental constitutional rights in the digital age, as well as the vigor with which the University of Oregon chose to defend unconstitutional policies,” noted Institute for Free Speech Senior Attorney Del Kolde. “The university made a costly decision to prioritize DEI principles over constitutional principles, aggressively litigating this case for nearly three years rather than acknowledging the obvious — that blocking someone for quoting the Declaration of Independence violates the First Amendment.” Local counsel Angus Lee added, “Oregon taxpayers and UO alumni should question why university officials spent such enormous sums defending the indefensible, especially when the university ultimately agreed to the very reforms Professor Gilley had sought from the beginning.”
The lawsuit began after the University of Oregon’s Division of Equity and Inclusion blocked Gilley from its official Twitter (now X) account in June 2022 after Gilley wrote “all men are created equal” when he reposted a university “racism interrupter” post. After significant litigation, including a successful appeal to the U.S. Court of Appeals for the Ninth Circuit and a decisive preliminary injunction ruling in July 2024, the parties reached a settlement in March 2025. The settlement required the university to implement comprehensive reforms to its social media guidelines, including:
Prohibiting viewpoint-based censorship
Creating an appeals process for those who believe they were wrongfully blocked
Conducting annual First Amendment training for social media managers
Maintaining judicial oversight for 180 days to ensure implementation
In recent years, a series of high-profile defamation cases have wound up in bankruptcy court, involving such colorful characters as Rudy Giuliani, Alex Jones, and Cardi B. As demands and verdicts swell with the rise of social media in a polarized age, defamation defendants are filing for bankruptcy more frequently and at earlier stages of litigation. But that doesn’t mean bankruptcy is a magic wand for waving away debt. To the contrary, much defamation debt may be nondischargeable as “willful and malicious” under section 523 of the Bankruptcy Code. Of course, consumer bankruptcy attorneys are all too familiar with bankruptcy’s discharge exceptions, but some courts are now starting to apply the exceptions to small businesses attempting to reorganize under subchapter V of the Code — a category that includes Alex Jones’s InfoWars.
Defamation law is coming to bankruptcy court, and it’s bringing the First Amendment with it. Yet scholars and practitioners have not yet placed these three areas of law — defamation, bankruptcy, and the First Amendment — next to each other. This Article provides both theoretical and practical guidance to litigants and lawyers, showing how bankruptcy’s substantive and procedural rules will process defamation debt, including when the First Amendment protections of New York Times v. Sullivan and related cases are triggered. The ensuing mixture is a cocktail of torts, contracts, civil procedure, federal courts, and constitutional law.
When speech injures others, compensation and punishment are in order. Yet forgiveness and a fresh start have their place as well. As to individuals, defamation debt should cause us to reflect on whether our “fresh start” policy in bankruptcy is too anemic. As to business entities, the defamation cases continue to raise the specter of whether Chapter 11 makes it too easy for bad actors to shed debt without compensating victims, suffering consequences, or reforming behavior. Either way, attorneys must be prepared to provide forward-thinking legal advice about bankruptcy whenever insolvency is on the horizon.
Ronnie Marmo is currently touring his critically acclaimed one-man show, “I’m Not A Comedian… I’m Lenny Bruce.” Marmo wrote the show, which is directed by Tony Award-winning stage and television star Joe Mantegna and has just celebrated eight years and 454 performances. The show will be coming to the Washington Center for the Performing Arts on June 28th at 7:30 pm.
Marmo also directs and stars as Bill Wilson in Bill W. and Dr. Bob, which is the origin story of Alcoholics Anonymous and is currently enjoying a multi-venue sit-down run in Los Angeles. Marmo is an acclaimed playwright, director, actor, and producer who has starred in more than 80 feature films and television shows, most recently guest starring on FBI: Most Wanted, Ghosts, Lethal Weapon and Criminal Minds. Marmo enjoyed a three-year run on ABC’s General Hospital as Ronnie Dimestico. On film, he starred in Ammore E Malavita (Love and Bullets), an Italian musical film which won the David di Donatello for best picture (the Italian equivalent to the Academy Award).
Debra Stephens joined the Washington State Supreme Court in January 2008 and began serving a second time as chief justice in January 2025. She was previously a judge for Division Three of the Court of Appeals and practiced law and taught as an adjunct professor at Gonzaga University School of Law. Her appellate career included more than 125 appearances in the Washington State Supreme Court, in addition to appearances in other state and federal courts and as counsel of record in the United States Supreme Court.
Chief Justice Stephens is deeply involved in efforts to advance justice and improve the legal system. She served on Washington’s Civic Learning Council and Minority & Justice Commission, is a founding board member of the National Courts and Sciences Institute (NCSI) and a board member of the National Judicial College’s Dividing the Waters program. She co-chairs the Washington Board for Judicial Administration and the National Association of Women Judges’ Judicial Independence Committee.
Robert Corn-Revere has been a First Amendment litigator for more than four decades. He currently serves as chief counsel for the Foundation for Individual Rights and Expression. In 2023, he joined FIRE from the law firm of Davis Wright Tremaine where he was a partner for 20 years. Before his time at DWT, he was a partner at Hogan & Hartson and served as legal advisor and later chief counsel to Federal Communications Commission Chairman James H. Quello.
2024-2025 SCOTUS term: Free expression and related cases
Cases decided
Villarreal v. Alaniz(Petition granted. Judgment vacated and case remanded for further consideration in light of Gonzalez v. Trevino, 602 U. S. ___ (2024) (per curiam))
Murphy v. Schmitt (“The petition for a writ of certiorari is granted. The judgment is vacated, and the case is remanded to the United States Court of Appeals for the Eighth Circuit for further consideration in light of Gonzalez v. Trevino, 602 U. S. ___ (2024) (per curiam).”)
TikTok Inc. and ByteDance Ltd v. Garland (9-0: The challenged provisions of the Protecting Americans from Foreign Adversary Controlled Applications Act do not violate petitioners’ First Amendment rights.)
Yost v. Ohio Attorney General (Kavanaugh, J., “IT IS ORDERED that the March 14, 2025 order of the United States District Court for the Southern District of Ohio, case No. 2:24-cv-1401, is hereby stayed pending further order of the undersigned order of the Court. It is further ordered that a response to the application be filed on or before Wednesday, April 16, 2025, by 5 p.m. (EDT).”)
Free speech related
Mahmoud v. Taylor (argued April 22. Free exercise case: issue: Whether public schools burden parents’ religious exercise when they compel elementary school children to participate in instruction on gender and sexuality against their parents’ religious convictions and without notice or opportunity to opt out.)
Thompson v. United States (Decided: 3-21-25/ 9-0 w special concurrences by Alito and Jackson) (interpretation of 18 U. S. C. §1014 re “false statements”)
This article is part of First Amendment News, an editorially independent publication edited by Ronald K. L. Collins and hosted by FIRE as part of our mission to educate the public about First Amendment issues. The opinions expressed are those of the article’s author(s) and may not reflect the opinions of FIRE.
