The U.S. Department of Justice is quickly implementing President Donald Trump's plan to seek huge sums of money from litigants whose cases impede his agenda but ultimately prove unsuccessful, court records show.

In numerous filings, the DOJ has invoked an obscure legal mechanism in an attempt to impose staggering costs on plaintiffs who lose cases after initially winning injunctions against White House policies. The department's efforts follow a March 6 memorandum in which Trump decried "sweeping injunctions far beyond the scope of relief contemplated by the Federal Rules of Civil Procedure" — and then committed to using one of those rules to deter legal challenges.

Specifically, Trump directed agencies represented by the DOJ to demand security under Rule 65(c), which requires plaintiffs to post bonds before judges pause challenged actions. During much of its long history, aggressive use of the rule has been more common in litigation between private parties than in challenges to federal policies, according to court documents. Now, however, it will be utilized in virtually "all lawsuits filed against the federal government" that seek injunctions with quantifiable costs, the president warned in his memo.

The Trump administration is already making good on that pledge, according to a Law360 review of dockets in the roughly 140 lawsuits filed against the government since Inauguration Day. Court filings reveal that the DOJ, with little success so far, has sought millions of dollars — and hinted at seeking billions of dollars — as security that plaintiffs might have to pay if any early injunctions are later dissolved.

"Should the court issue an injunction at this preliminary stage ... defendants request that plaintiffs post a bond of $32 million," the government told a Washington, D.C., federal judge in an immigration case, Amica Center v. DOJ, right before the release of Trump's memo. That amount "is approximately equal to the amount of money" earmarked in 2025 to legal assistance programs for noncitizens, the DOJ said.

Nonprofit plaintiffs responded by insisting the DOJ is intent on "pricing plaintiffs out of court," and they spotlighted a White House description of Trump's directive as a deterrent against "meritless suits for fundraising and political gain." But deterring litigation is "not a legitimate argument" under Rule 65(c), and asking small nonprofits to pony up $32 million "further demonstrates defendants' unconstitutional goal to cut congressionally appropriated funding without judicial review of their actions," the groups asserted.

Other organizations have echoed that rebuttal. "The court should reject the administration's attempt to wield Rule 65(c) for the purpose of deterring organizations like plaintiffs from bringing litigation that vindicates their constitutional rights," civil rights groups wrote in a March 17 motion opposing any bond requirement in their challenge to executive orders regarding diversity, equity and inclusion.

Even before Trump's memo, some advocates of stricter Rule 65(c) enforcement explicitly acknowledged a desire to make litigation unaffordable for groups seeking to stymie administration initiatives.

"The activists, they can't post a $100 million bond. They might lose, and then that money's gone," Daniel Huff, a former visiting fellow at the Heritage Foundation, said in a video produced for Project 2025, an elaborate blueprint that Heritage created for a Republican presidential administration.

Huff was a White House legal adviser in Trump's first administration. In the video published in August 2024 by news outlets ProPublica and Documented, he lamented liberal-led lawsuits and the past decisions of GOP administrations not to invoke Rule 65(c): "It's this litigation, which has been killing us in area after area after area, and if we can stop that by requiring them to post bond, it would be fantastic. All this liberal litigation would grind to a halt. And yet, Republican Justice Departments don't seek them."

​Representatives of the White House and the DOJ didn't respond to inquiries seeking comment for this article.

It's not certain the DOJ's nascent pursuit of budget-busting bonds will scare off potential plaintiffs. That's mainly because of precedent in many circuit courts giving district judges leeway to require nominal security or none at all. Such leeway has existed since the early years of Rule 65(c), which debuted in 1938 with the original Federal Rules of Civil Procedure and has undergone modest tweaks over the years.

"Judges have been permitted to grant interlocutory injunctions without security on the ground that Federal Rule 65(c) leaves it to the court to set the bond in such sum as it deems proper," a Harvard Law Review article observed in 1959.

But some scholars see little downside in testing the prevailing precedent. They find reasons for optimism in the text of Rule 65(c), which makes security sound mandatory, even if it also allows some flexibility. "The court may issue a preliminary injunction or a temporary restraining order only if the movant gives security in an amount that the court considers proper," the rule states.

In an interview with Law360, John G. Malcolm, a Heritage Foundation vice president, acknowledged that Rule 65(c) gives district judges some latitude. But that latitude might have limits, especially in cases implicating enormous amounts of federal spending, Malcolm added.

"It certainly provides for some discretion, but I'm not sure that that discretion is limitless," he said. "I mean, if we're talking about billions of dollars, and somebody comes forward and says, 'Well, I think the proper amount for a bond is zero,' [judges] can abuse discretion. And I think some further case law on that subject would be welcome."

Further case law does, in fact, appear likely to emerge soon. The DOJ is now lodging Rule 65(c) requests regularly — Law360 identified nearly 20 such requests in cases against the Trump administration — and several district judges have already issued rulings, teeing up appeals with high stakes for the Trump administration's legal battles.

Moreover, the Rule 65(c) initiative is fueling fresh debate regarding nationwide injunctions from individual district judges — a phenomenon that's been championed at various times by observers of all ideological stripes, but also described as improper by many lawyers and lawmakers.

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With Rule 65(c) skirmishes suddenly breaking out in wide-ranging cases, the DOJ and assorted plaintiffs are pointing to precedent dating back decades. Much of that precedent is from litigation between private parties and offers debatable guidance for determining bond amounts, as courts have set security at dramatically different levels in comparable circumstances.

A 1995 study in the Hastings Law Journal, for example, noted that judicial discretion has led to dissimilar treatment of similarly situated private litigants. That study described two groups of retirees who sued separately over reduced benefits in the 1990s; one group's bond was set at a nominal $250, while the other's was set at $7 million — the amount a defendant company stood to pay out annually while benefit reductions were enjoined.

The Trump administration and plaintiffs have also cited Rule 65(c) precedent from cases against the federal government, but little of that precedent involves Uncle Sam requesting multimillion-dollar bonds in public interest litigation. When such requests have been made, they haven't always gone over well.

A prominent example occurred in a 1968 case, Powelton Civic Home Owners Association v. Department of Housing and Urban Development , that plaintiffs have frequently cited in recent weeks. In that case, HUD sought $20 million in security, but a Pennsylvania federal judge penned a forceful rebuke, writing that a bond requirement of that size "would effectively prevent judicial review of [HUD's] decision in this and in every other case."

"We cannot accept the proposition that Rule 65(c) was intended to raise virtually insuperable financial barriers insulating the agency's decisions from effective judicial scrutiny," U.S. District Judge Ralph C. Body wrote.

Courts have sometimes, however, accepted lower financial barriers, even when groups of modest means are challenging agency decisions. The DOJ, for instance, recently spotlighted a 2010 opinion from the Seventh Circuit, which affirmed a $10,000 bond against a nonprofit that challenged national forest logging. The opinion in Habitat Education Center v. U.S. Forest Service rejected the idea of exempting nonprofits, saying "the argument flies in the face of Rule 65(c)."

But the five-figure bond in that case is dwarfed by the Trump administration's bond ambitions. In perhaps its most provocative request, the DOJ on March 11 floated the prospect of costs and damages hitting the 10-figure mark. ​The DOJ did so in litigation involving refugee admissions, and it used the prospect of a multibillion-dollar bond as leverage, suggesting the amount could be slashed dramatically if any injunction were narrow in scope.

"The risk of harm here is not insubstantial, as Congress has appropriated nearly $4 billion to refugee funding," the DOJ told a federal judge in Washington state. "This underscores the need to limit relief to named plaintiffs, such that plaintiffs would only need to provide a security bond" for a subset of cooperative agreements.

In a March 24 ruling, U.S. District Judge Jamal N. Whitehead wrote that he was "not persuaded" by the government's logic, and that he would not require any security at all, because a ruling against the suspension of refugee services "merely compels the government to spend funds that have already been appropriated by Congress."

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Without much precedent solidly supporting its desire for super-size security, the DOJ has seemingly tried to make the best of judicial discretion. If judges can say the proper security amount is zero, they can also say the proper amount is much larger, DOJ filings have suggested.

Those filings have often relied on the D.C. Circuit's 1999 opinion in DSE Inc. v. U.S., which said Rule 65(c) vests "broad discretion in the district court to determine the appropriate amount of an injunction bond." DOJ filings have cited that opinion in several contexts, including the $32 million security request in Amica Center v. DOJ and a $7.5 million security request in litigation involving Radio Free Europe/Radio Liberty.

But in opinions so far regarding Trump administration requests, district judges have given the White House little more than disappointment, setting security at amounts ranging from nothing to slightly more than nothing. Perhaps most striking was an opinion from U.S. District Judge Loren L. AliKhan, whose ruling against a federal spending freeze concluded by balking at the government's request for "a bond commensurate with the scope of the relief ordered."

"In a case where the government is alleged to have unlawfully withheld trillions of dollars of previously committed funds to countless recipients, it would defy logic — and contravene the very basis of this opinion — to hold plaintiffs hostage for the resulting harm," Judge AliKhan wrote. A few days before that opinion, when Judge AliKhan dubbed the bond request "curious," a DOJ attorney noted that the government in 2020 lodged an unsuccessful bond motion in TikTok litigation.

Another recent order of note occurred in litigation brought by 19 states over probationary worker firings. The order from U.S. District Judge James K. Bredar set security at $100 per state, concluding that the government's potential costs were "too complex" to calculate quickly and would, in any event, be "prohibitive" for the plaintiffs. The DOJ sought emergency relief at the Fourth Circuit, saying the judge "abused [his] discretion by setting the amount of the bond at a nominal $100 per plaintiff state — which, on its face, is not 'proper' to protect the interests of the government."

In other rulings against the administration, judges have cited public-interest considerations or expressed skepticism regarding the government's fears of financial injuries.

For example, U.S. District Judge Myong J. Joun — in a case involving cuts to teacher training grants — held in March that "no security is necessary under Rule 65(c)," citing "important federal rights" and "a mechanism for recouping allocated funds." That case is now before the U.S. Supreme Court, where acting U.S. Solicitor General Sarah M. Harris on Wednesday urged the justices to "put a swift end to federal district courts' unconstitutional reign as self-appointed managers of executive branch funding."

Elsewhere, U.S. District Judge Adam B. Abelson set a zero-dollar bond in litigation involving diversity programs, saying courts have "frequently waived the bond requirement in cases where a fundamental constitutional right is at stake." And in a case involving gender-affirming medical care, U.S. District Judge Lauren King declined to impose a bond after writing that "defendants have shown no evidence of a likelihood of harm, monetary or otherwise."

The Rule 65(c) skepticism from the federal bench has been so pronounced that judges at times have rejected security that the DOJ didn't even seek. For example, in a mid-March opinion ordering the reinstatement of certain probationary employees, U.S. District Judge William Alsup wrote, "The court found security — which defendant did not request — to be proper in the amount of $0."

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Regardless of whether the Rule 65(c) campaign gains traction, it has already succeeded in adding urgency to some of the legal community's most heated debates. One of those debates centers on Trump's treatment of opposing counsel; on the same day as his Rule 65(c) memo, the president issued a directive targeting Perkins Coie LLP, then followed up with a now-rescinded directive targeting Paul Weiss Rifkind Wharton & Garrison LLP and additional orders aimed at Jenner & Block LLP and WilmerHale.

Amid those actions, Trump released a sweeping memo directing the U.S. attorney general to "seek sanctions against attorneys and law firms who engage in frivolous, unreasonable and vexatious litigation."

Skye Perryman, president and CEO of Democracy Forward — a left-leaning group that's been litigating many cases against the Trump administration — highlighted the Rule 65(c) memo and the law firm directives in a recent statement accusing the White House of pursuing "a course of retribution and intimidation."

Another simmering debate centers on district judges enjoining federal policies nationwide; in recent years, Democrat-nominated judges have issued nearly all such injunctions against Trump administration policies, while Republican-nominated judges delivered all such injunctions against Biden administration policies, according to a recent study in the Harvard Law Review.

National injunctions skyrocketed in Trump's first term, perhaps reflecting "the unprecedented degree to which President Trump tested the limits of presidential power," and while national injunctions declined greatly under Biden, there was a simultaneous rise in vacatur orders, the study found.

Sen. Chuck Grassley, R-Iowa, chairman of the Senate Judiciary Committee, extensively cited that study in a March 14 letter to U.S. Attorney General Pam Bondi regarding the president's Rule 65(c) directive. "Although President Trump has been the target of much of this judicial overreach, the issue is bipartisan," and "by requiring a bond or security, the defendant is protected from an erroneous injunction or restraining order," Grassley wrote, adding that "the bond deters frivolous lawsuits."

Grassley also noted that Congress has been debating legislative remedies; the House Judiciary Committee recently endorsed the No Rogue Rulings Act, which would restrict district courts' ability to enjoin policies nationwide, and Grassley announced Sunday that he would introduce similar legislation, the Judicial Relief Clarification Act, in advance of a Senate Judiciary Committee hearing Wednesday about nationwide injunctions.

In Grassley's letter to Bondi — an elaborately researched document with 27 footnotes, including several citing a recent Fox News column by Huff, the former Heritage Foundation staffer — the senator said he would be closely following the Rule 65(c) issue, and concluded with a handwritten message imploring her to be bold.

"Pam: This is a very important issue for me!" Grassley wrote. "Please take strong action!"

The cases include American Federation of Government Employees et al. v. U.S. Office of Personnel Management et al., case number 3:25-cv-01780, in the U.S. District Court for the Northern District of California; Organized Communities Against Deportation et al. v. Trump et al., case number 1:25-cv-00868, and Chicago Women in Trades v. Trump et al., case number 1:25-cv-02005, both in the U.S. District Court for the Northern District of Illinois; California et al. v. U.S. Department of Education et al., case number 1:25-cv-10548, in the U.S. District Court for the District of Massachusetts; City of New York v. Trump et al., case number 1:25-cv-01510, in the U.S. District Court for the Southern District of New York; Pacito et al. v. Trump et al., case number 2:25-cv-00255, and State of Washington et al. v. Trump et al., case number 2:25-cv-00244, both in the U.S. District Court for the Western District of Washington; National Association of Diversity Officers in Higher Education v. Trump, case number 1:25-cv-00333, Does 1-26 v. Musk et al., case number 8:25-cv-00462, American Federation of State, County and Municipal Employees et al. v. Social Security Administration et al., case number 1:25-cv-00596, and State of Maryland et al. v. U.S. Department of Agriculture et al., case number 1:25-cv-00748, all in the U.S. District Court for the District of Maryland; State of Maryland et al. v. U.S. Department of Agriculture et al., case number 25-1248, in the U.S. Court of Appeals for the Fourth Circuit; and National Council of Nonprofits et al. v. Office of Management and Budget et al., case number 1:25-cv-00239, American Oversight v. U.S. Agency For International Development et al., case number 1:25-cv-00719, National Urban League et al. v. Trump et al., case number 1:25-cv-00471, Catholic Charities Diocese of Fort Worth Inc. v. U.S. Department of Health and Human Services et al., case number 1:25-cv-00605, Amica Center For Immigrant Rights et al. v. U.S. Department of Justice et al., case number 1:25-cv-00298, Mennonite Church USA et al. v. Department of Homeland Security et al., case number 1:25-cv-00403, RFE/RL Inc. v. Kari Lake et al., case number, 1:25-cv-00799, and Centro de Trabajadores Unidos et al. v. Bessent et al., case number 1:25-cv-00677, all in the U.S. District Court for the District of Columbia.

--Additional reporting by Lauren Berg, Ali Sullivan and Courtney Bublé. Graphics by Ben Jay. Editing by Marygrace Anderson.