In the Trump Presidency, the Rules Are Vague. That Might Be the Point.

 

In the Trump Presidency, the Rules Are Vague. That Might Be the Point.

The U.S. has long believed that unspecific laws threaten democracy. So why is the administration being so vague?

By Matthew Purdy

• Published Oct. 30, 2025Updated Nov. 4, 2025

Last July, a federal judge named William G. Young issued a searing 103-page opinion that examined the rush to carry out President Trump’s executive orders in the early months of the administration. Young, a Reagan appointee in Boston, was ruling on challenges brought by state officials and health care professionals over the sweeping cancellation of research grants by the National Institutes of Health. Young laid into the administration for what he said were indiscriminate cancellations based on “wholly unsupported statements” in executive orders on race and gender.

He said diversity, equity and inclusion efforts in particular were set up as “some sort of boogeyman” in Trump’s executive orders, with “no operative definition.” Administration officials, he concluded, “decided that they are going to ‘eradicate’ something that they cannot define.”

Federal District Court judges across the country and across the political spectrum, including some Trump appointees, have echoed Young’s critique, faulting the administration for using broadly cast executive orders and policies to justify “arbitrary and capricious” actions.

Many of these judges have explicitly invoked something called the vagueness doctrine, a concept that for centuries has been foundational to American law. The notion is simple: Unless laws are clearly stated, citizens cannot know precisely what is and is not permitted, handing authorities the power to arbitrarily decide who is in violation of a law or rule. Vagueness has long been seen as a clear divide between democracies run by laws and autocracies run by strongmen, leading American administrations of both parties to routinely criticize foreign governments for using vague laws to suppress unwanted speech and behavior.

But vagueness has become fundamental to the way Trump operates. It is not so much a legal strategy as a power dynamic. Declaring war on “woke culture,” he has shaken education and private industry with threats of financial penalties or investigations for “promoting gender ideology” or “illegal D.E.I.,” two terms that judges have criticized as ill defined. Inside the government, aides have dutifully applied his executive-order terminology to chop through the federal bureaucracy and to slash thousands of government grants. He has threatened to financially punish law firms that he declares are operating contrary to the “national interest,” an undefined standard he bases partly on their association with cases he doesn’t like and lawyers he sees as enemies.

In a sense, Trump is creating a system of rules and punishments all his own. And when those rules are vaguely defined — unlike, say, a speed limit or even complex financial regulations — there is no assurance that anyone can be safely outside the zone of violation. Therefore, there is no telling who might be found out of bounds next and what punishment might be imposed.

As a private citizen, even Trump saw the dangers of vagueness. When he was facing an indictment for unauthorized retention of classified documents after his first term, his lawyer Todd Blanche, now the deputy attorney general, argued in a brief that the underlying law was vague, “conferring unfettered and wholly subjective enforcement discretion to the executive branch. That is one of the principal evils that the vagueness doctrine was established to avoid.”

As president, Trump has flipped the script. Following the killing of the right-wing provocateur Charlie Kirk, Trump and his associates appear to be drawing up a fresh batch of broadly defined violations to catch their political enemies — a strategy critics say is akin to how authoritarians use vague accusations to target opponents. Administration officials first encouraged severe consequences for anyone violating their undefined rules for criticizing Kirk on social media. Then they undertook an administration-wide assault on political violence, aimed at a “network” of leftist groups that they have broadly asserted, in the words of Vice President JD Vance, “foments, facilitates and engages in violence.”

Vagueness breeds trepidation, perhaps the desired result. “We want you to fear,” Steve Bannon, a former Trump aide and a prominent cheerleader, said last year, anticipating a second term.

Tom Ginsburg, an international law professor at the University of Chicago who has written about the decline of democracies around the world, says inducing worry is effective. “You get a lot of anticipatory compliance, which is cheap. And vagueness is part of the tool kit.”

Fear can seep in anywhere — even at august public institutions and in corporate boardrooms. But its depth is perhaps best measured in more ordinary spaces, like middle school classrooms. Valerie Wolfson, the 2024 New Hampshire history teacher of the year, is wrestling with a federal order accusing all schools of “indoctrinating” students about racism in American history and ordering them to stop “illegal D.E.I.” or risk losing funding. Judges have declared the term impermissibly vague, but it remains a quandary for Wolfson, whose post-Civil War curriculum includes Reconstruction, the rise of the K.K.K. and the Jim Crow era. “I do not know how I could discuss them without creating a risk of being accused of presenting a narrative of the United States as racist,” she says.

Vagueness can be seen as a kind of force multiplier for Trump. After Young ruled against the administration in the N.I.H. case, an appeals court upheld his decision, mirroring his finding that “the prohibited categories of research grants were never defined, thus allowing the department to terminate any grant that it wanted to, for any reason.”

But the Supreme Court saw it differently, ruling in August in the administration’s favor. The majority did not focus on the lower courts’ findings of murky directives, but instead said any claims for terminated grants should have been brought to the Court of Federal Claims, not a district court. Only Justice Ketanji Brown Jackson pointed out in her dissent the “definitional void” at the center of the cancellation of more than $780 million in grants.

In a dig at her colleagues, she resorted to citing a comic strip. “This is Calvinball jurisprudence with a twist,” she wrote, a reference to the game of ever-changing, self-serving rules created by the child protagonist in “Calvin and Hobbes.” “Calvinball has only one rule: There are no fixed rules,” Jackson wrote. “We seem to have two,” she continued, the second being “This administration always wins.”

Vagueness has been seen as antithetical to due process and the rule of law since the earliest days of American democracy. The nation’s founders, building on English law, warned in the Federalist Papers against laws “so incoherent that they cannot be understood” or those that change so often “that no man, who knows what the law is today, can guess what it will be tomorrow.”

Vagueness thrived in the dark corner of antivagrancy laws. Under the post-Civil War Black Codes, the authorities arrested and sometimes effectively re-enslaved Black people who were caught without proof of employment. A hundred years later, vagrancy laws allowed the police to detain people for such broadly defined crimes as “wandering or strolling around from place to place without any lawful purpose or object.” Caught in the web were the poor and the disfavored, including racial and ethnic minorities as well as gay people and civil rights protesters.

In 1972, the Supreme Court reaffirmed the concept that laws could be “void for vagueness,” declaring unconstitutional a Jacksonville, Fla., law that criminalized a long and loose list of conduct by so-called vagrants. In his landmark opinion, Justice William O. Douglas wrote that the law furnished “a convenient tool for ‘harsh and discriminatory enforcement by local prosecuting officials, against particular groups deemed to merit their displeasure.’”

Nearly 50 years later, Justice Neil M. Gorsuch wrote in a 2018 Supreme Court opinion that “Vague laws invite arbitrary power.” Gorsuch, a reliable conservative, sided with his liberal colleagues to strike down a provision used to try to deport a Filipino man, a legal permanent resident, who was convicted of burglary. Gorsuch said the provision lacked clear criteria to judge whether the man’s crimes met the standard for deportation. “A government of laws and not of men can never tolerate that arbitrary power,” he wrote.

For decades, the United States has held itself out to the world as the paragon of “laws not men” governance. During the first Trump administration, as vague laws aimed at suppressing dissent spread in Eastern Europe and beyond, the U.S. Embassy in Tbilisi, Georgia, issued a statement underscoring that tradition. The statement, titled “Authoritarian Regimes’ Unclear Laws Make Anyone a Suspect,” distinguished between vague laws used by authoritarians and American laws designed to guard against arbitrary power.

Today, the rulings of some American judges critical of Trump administration policies echo the language in that statement. “For laws to be just, they must be clear,” the embassy statement began. “Citizens must know what is — and is not — against the law.” It quoted Justice Antonin Scalia saying vague laws violate due-process protections, and it drew from an essay by Timothy Sandefur, a legal scholar at the conservative Goldwater Institute, saying, “Vagueness turns the law into a sword dangling over citizens’ heads — and because government officials can choose when and how to enforce their own interpretations of the law, vagueness gives them the power to make their decisions from unfair or discriminatory motives.”

The statement noted that China had imprisoned journalists and environmental activists under a law against “picking quarrels and provoking trouble” and that Iran had jailed women “for ‘propaganda against the state’ for simply declining to wear a hijab.”

It proudly declared, “The U.S. Constitution protects American citizens from this problem.”

None of Donald Trump’s edicts have deployed vagueness as effectively as his attack on D.E.I. It has altered behavior far beyond a president’s usual domain, leading corporations, schools and nonprofit organizations to eliminate diversity policies and change course offerings. Inside the government it has been wielded as a kind of executive Swiss Army knife — as useful for slashing government grants as for removing books from library shelves at military academies.

But less understood is the recipe that makes the anti-D.E.I. campaign so effective: equal parts vagueness and threat. The line between what is and isn’t allowed may be vague, but the penalty for crossing it is certain. The version cooked up by the Department of Education’s Office for Civil Rights is a textbook case.

Three weeks after Trump took office, the civil rights office sent school districts and colleges in America a “Dear Colleague letter” — a folksy bureaucratic term that belied its message. The letter, echoing Trump, asserted that “educational institutions have toxically indoctrinated students with the false premise that the United States is built upon ‘systematic and structural racism’ and advanced discriminatory policies and practices.” Schools were then asked to certify that they would cease all “illegal D.E.I.” and abide by the letter.

School districts found in violation could lose federal funds and face investigation under the False Claims Act — in this case, obtaining federal money by falsely claiming to ban D.E.I. Any entity violating the False Claims Act, which is commonly enforced against government contractors, can be fined three times the amount it received from the government. And citizens who provide evidence of a violation can share in the penalties.

To encourage whistle-blowers, the department established an online portal for “students, parents, teachers and the broader community to report illegal discriminatory practices” at schools. The announcement of the End D.E.I. portal quoted Tiffany Justice, a co-founder of Moms for Liberty, a right-wing group that pushes for greater parental control over schools, including banning books it finds inappropriate and defunding schools that adhere to views of race and gender it finds abhorrent. Justice said that after years of the group’s concerns about schools’ “pushing critical theory, rogue sex education and divisive ideologies” being ignored or mocked, “now is the time that you share the receipts of the betrayal.”

Lawsuits against the Education Department’s actions were filed across the country, and multiple federal judges called out the government for relying on vague language.

Dabney L. Friedrich, a federal judge in Washington who was nominated by Trump, said the government instructions “fail to provide an actionable definition of what constitutes ‘D.E.I.’ or a ‘D.E.I.’ practice, or delineate between a lawful D.E.I. practice and an unlawful one.”

At a hearing in Maryland on a case challenging the president’s broader anti-D.E.I. policy, U.S. District Judge Adam B. Abelson, a Biden nominee, struggled to get the government lawyer Pardis Gheibi to define terms like “equity related” government grant under the president’s executive order. He then asked a more concrete question.

“Let’s say the Department of Education funds computers in elementary schools,” he said. “Would it constitute illegal D.E.I. for a teacher to use one of those computers to teach about Jim Crow?”

“Your Honor,” Ms. Gheibi responded, “I can’t answer that hypothetical of that particular question.”

Despite what judges have said, a White House spokeswoman, Abigail Jackson, said in response to my queries that “anyone pretending President Trump’s policies are vague is living in an alternate universe. Certainly the dark-money activists attempting to pursue their preferred bad policies through the courts don’t find the president’s policies vague.”

In July Attorney General Pam Bondi issued a nine-page guide for recipients of federal funding, including schools, to avoid giving unlawful “preferential” treatment to one group that “disadvantages other qualified persons.” She vowed that the administration would “not stand by while recipients of federal funds engage in discrimination.”

The Dear Colleague letter had been temporarily enjoined by judges since April, and in August a federal judge in Maryland, Stephanie A. Gallagher, a Trump nominee, went a step further. She “vacated” the letter, saying the administration improperly “initiated a sea change in how the Department of Education regulates educational practices and classroom conduct.”

Her ruling, now on appeal, got to the crux of how vague laws can create unchecked power. Without clarity on what practices are permissible — including subjects teachers can teach — she wrote, “it is impossible to determine what conduct triggers the prohibitions and sanctions of the letter. That enables the government to enforce the letter arbitrarily.”

Vagueness may have been an obstacle inside the courtroom, but outside, the spirit of the letter lived on. The federal government had already begun investigations, according to court documents. And several states passed laws that echoed it.

One of those states was New Hampshire, where a high school English teacher was worried that teaching classics like Toni Morrison’s “Beloved,” Joseph Conrad’s “Heart of Darkness” or even Jane Austen’s “Pride and Prejudice” could push him over the invisible line of “indoctrinating” students on race or gender. “There’s that witch-hunt aspect of this,” he says, on the condition of anonymity because he fears retribution. “There’s a chill that’s gone through the classroom.” He made some adjustments in his curriculum. He still assigned students to read “Beloved,” the haunting tale of a formerly enslaved woman that has been targeted for banning by some Moms for Liberty supporters, but he no longer talked about the book in class.

The message — and the threat — from the Department of Education was received loud and clear across the country. In February, Amy Parsons, the president of Colorado State University, wrote to her campus that while “we are confident that the institution currently complies with the law,” given its “reliance on federal funding, it is necessary to take additional steps to follow the federal administration’s new interpretations.” She laid out a host of changes in programs, but in June, America First Legal, a group founded by Trump’s deputy chief of staff, Stephen Miller, filed a federal civil rights complaint against the university. “It appears the University’s ‘additional steps’ are merely superficial reorganizations of titles and programs designed to avoid federal detection,” the group claimed.

In March, the department announced that it was investigating 45 universities for violating the rules of the Dear Colleague letter by working in partnership with a 30-year-old nonprofit called the PhD Project. The organization had guided students from historically underrepresented groups to seek advanced degrees in business, but changed its policy to help all students just before Trump took office, according to its chairman, Alfonzo Alexander. Even so, the specter of an investigation turned any association with the previously obscure program into a stigma. At last count, only 76 of its 230 college partners remained. “The threat of them losing funding, more than anything, was pivotal,” Alexander says.

Today strongmen around the world often use vague laws to constrain groups that challenge their power. Beginning in Russia and copied by many other countries, these measures have tightened the grip on the opposition under the guise of stamping out foreign influence, terrorism or activity that destabilizes society.

Last year, a top State Department official wrote about the true intent of laws aimed at nongovernmental organizations: “Russia uses broad, vague legislation on purported foreign agents as a cudgel to threaten dissenting voices into silence and disable independent civil society.” In 2020, the Trump State Department said China’s NGO regulations “prevented the formation of autonomous political, human rights, religious, spiritual, labor and other organizations that the government believed might challenge its authority in any area.”

At a Senate Foreign Relations Committee hearing in September 2024, Senator Jim Risch, an Idaho Republican, called these laws “the tool of choice for authoritarians” and said of the spreading trend, “This is a bipartisan issue, it’s an American issue.”

“These laws claim to stop foreign influence but in reality are used to close the space for civil society and opposition,” Risch added. “Autocrats fear the loss of control, and this ensures opposing ideas are neither seen nor heard.”

In February, Trump seemed to take a page from the global anti-NGO agenda, ordering government agencies to end funding of “NGOs that undermine the national interest” — one of his go-to undefined justifications.

After Kirk’s murder, the president said the administration would attack political violence by bearing down on “the radical left,” mentioning some large Democratic donors and bluntly saying “I couldn’t care less” about violence on the right. One key leader of the effort is Miller, who has called the Democratic Party “a domestic extremist organization.”

A national security presidential memorandum Trump signed on Sept. 25, “Countering Domestic Terrorism and Organized Political Violence,” has echoes of the unbridled language of foreign laws criticized by the United States as providing cover for suppressing opponents:

“Common threads animating this violent conduct,” it read, “include anti-Americanism, anticapitalism and anti-Christianity; support for the overthrow of the United States Government; extremism on migration, race and gender; and hostility toward those who hold traditional American views on family, religion and morality.”

Uzra Zeya, who served as under secretary of state for civilian security, democracy and human rights in the Biden administration, reacted with alarm. “This memo represents a dangerous obfuscation of real threats with peaceful dissent,” she said.

One foreign leader whose list of offending groups and “ideologies” overlaps somewhat with Trump’s is Viktor Orban, the far-right prime minister of Hungary, often lauded by MAGA leaders. A prime target Trump identified in previewing the anti-violence campaign was George Soros, a Hungarian émigré and billionaire who funds pro-democracy and Democratic initiatives. Coincidently or not, Soros also is a longtime target of Orban’s.

David Pressman, the ambassador to Hungary during the Biden administration, watched as Orban imposed broadly drawn, restrictive laws in his country. Legislation granting the government additional powers to manage the Covid crisis was expanded to include criminal penalties for spreading “distorted truth” or for “scaremongering” across a swath of issues. A law aimed at protecting children from predators ended transgender legal recognition and restricted some activities around gender identity and L.G.B.T.Q. expression, including Pride events. Hungary, following Russia’s lead, established an agency to probe NGOs as agents of foreign influence, under the guise of protecting “national sovereignty.”

Pressman says recent authoritarian leaders tend to enact broad rules to give themselves the cover of operating legally. “One of the things that strongmen do,” he says, “is they try to construct and ‘legalize’ systems that allow for the arbitrary use of power by constructing benefits for those who are compliant and consequences for those who are not.”

Pressman was ridiculed for being gay by the government from the time he arrived in Budapest, which he saw as a way of discrediting him as critic of anti-democratic moves. “In Hungary, the use of vague restrictions and laws was a device to signal who was acceptable and who was radioactive,” he says.

Last year, Pressman issued a warning in a speech to the Budapest Forum, a pro-democracy conference, about government investigations of political opponents. “In Hungary,” he said, “the choice of whether to engage in political debate, especially of whether to oppose the ruling party, has increasingly become existential.”

Pressman resigned from the State Department after Trump’s election, and in February he rejoined the law firm Jenner & Block. In short order, he got a lesson in the cost of opposing the government back home.

In March, Jenner & Block became a target in Trump’s assault on law firms that had drawn his personal disdain. In an executive order, he accused the firm of engaging in cases that “undermine justice and the interests of the United States.” When Jenner and other firms sued, judges zeroed in on what they saw as the problematic combination of vague allegations and very specific and damaging threats like cutting the firm’s access to public buildings, security clearances and government contracts. In a sense, it mirrored the dynamic that judges found in the Dear Colleague letter.

Trump accused the law firms of variously eroding “bedrock American principles” or engaging “in conduct detrimental to critical American interests,” but what they shared was past association with lawyers involved in investigations of Trump. He said Jenner & Block’s previous employment of a lawyer involved in investigating Russian influence in the 2016 election “is a concerning indictment of Jenner’s values and priorities.”

Judge Beryl A. Howell, an Obama nominee ruling in a challenge to Trump brought by the firm Perkins Coie, said that the president was sending a clear message: “Lawyers must stick to the party line, or else.”

Perkins Coie has been in the president’s sights for years because of its work with the Hillary Clinton campaign, and for hiring a group that helped create the discredited dossier on Trump’s ties to Russia. Among its other purported misdeeds included working with George Soros and unspecified employment discrimination. Given the lack of evidence on employment discrimination, she said the firm was left “to guess at what is and is not permissible in the government’s view, while already facing adverse actions during the guessing.”

Trump did not hide that he was seeking to exact revenge, nor was it lost on the judges. In the case of another law firm, WilmerHale, Judge Richard J. Leon, a George W. Bush nominee, said he agreed with the firm’s assertion that the executive order left “no doubt that WilmerHale is being punished because it has represented some of the president’s political opponents and advanced positions with which he disagrees.”

“The order essentially leaves it to WilmerHale to predict which causes and which attorneys the president personally dislikes and then steer clear of those causes and attorneys,” he wrote. “This chilling effect triggers serious vagueness concerns.”