List of Unconstitutional Executive Orders Struck Down by Courts

Federal courts have struck down or blocked presidential directives in every era of American history when those orders overstepped the Constitution or encroached on powers the Constitution assigns to Congress. The list of unconstitutional executive orders struck down by courts runs from Lincoln’s Civil War habeas corpus suspension to Truman’s seizure of the steel mills to a cascade of rulings during President Donald Trump’s second term, when more than 800 lawsuits challenging administration policies have produced hundreds of injunctions and several major Supreme Court decisions against the executive branch.

How Courts Decide an Executive Order Is Unlawful

There is no single statute that governs judicial review of executive orders. The Supreme Court held in Franklin v. Massachusetts (1992) that the Administrative Procedure Act does not reach the president directly, which leaves courts applying a patchwork of constitutional and statutory doctrines.¹

The dominant framework comes from Justice Robert Jackson’s concurrence in Youngstown Sheet & Tube Co. v. Sawyer (1952). It sorts presidential power into three tiers. The president’s authority is strongest when acting with the express or implied authorization of Congress. It sits in a “zone of twilight” when Congress has not spoken. It is at its “lowest ebb” when the president acts contrary to Congress’s expressed will.²

Courts also test executive orders against the Bill of Rights and the structural separation of powers. A directive that abridges speech, denies due process, or spends money Congress has not appropriated is vulnerable regardless of where it falls on the Youngstown scale.

Historic Executive Orders Struck Down by the Supreme Court

A handful of rulings anchor the doctrine and still shape challenges filed today.

Ex parte Merryman (1861). Chief Justice Roger Taney, sitting as a circuit judge, ruled that Lincoln’s order authorizing military commanders to suspend the writ of habeas corpus was unconstitutional because only Congress holds that power.²
Ex parte Milligan (1866). The Supreme Court struck down Lincoln’s order allowing military trials of civilians in areas where civilian courts were still functioning, holding it violated the right to a jury trial.²
Panama Refining Co. v. Ryan and Schechter Poultry Corp. v. United States (1935). The Court invalidated Franklin Roosevelt’s orders under the National Industrial Recovery Act, ruling that Congress had delegated legislative power to the president without adequate standards.²
Youngstown Sheet & Tube Co. v. Sawyer (1952). In a 6-3 decision, the Court struck down Harry Truman’s order seizing the nation’s steel mills during the Korean War, holding that the president could not take private property without congressional authorization.²
Hamdan v. Rumsfeld (2006). In a 5-3 ruling by Justice John Paul Stevens, the Court held that George W. Bush lacked congressional authority to establish military commissions for Guantánamo detainees, and that the commissions violated both the Uniform Code of Military Justice and the Geneva Conventions.³

The Current Wave of Rulings Against Trump Executive Orders

The second Trump term has produced the largest volume of successful challenges to presidential orders in modern history. The Just Security litigation tracker at NYU Law counts 803 cases as of mid-2026. Plaintiffs have secured some form of victory in 262 of them: 64 cases with the government action permanently blocked, 137 temporarily blocked, and 27 closed in the plaintiff’s favor. The government has prevailed in 126 cases, and 360 remain pending.⁴ The ACLU alone has filed 239 legal actions and reports a success rate of roughly 65 percent in delaying, narrowing, or defeating challenged policies.⁵

The orders below are the ones courts have most prominently found unconstitutional, unlawful, or likely so.

Birthright Citizenship

On January 20, 2025, Trump signed an executive order declaring that children born in the United States would not automatically receive citizenship if both parents were in the country illegally or temporarily. Three federal district judges blocked the order, finding it likely violated the Fourteenth Amendment, which states that all persons born in the United States and subject to its jurisdiction are citizens.⁶

On October 3, 2025, the First Circuit upheld the block and warned against abandoning the “established tradition of recognizing birthright citizenship,” rejecting the administration’s argument that citizenship should turn on parental conduct rather than birth on U.S. soil.⁷

A separate class action, Barbara v. Trump, certified a class of all babies subject to the order. The Supreme Court heard oral arguments on April 1, 2026, and as of mid-2026 has not issued a decision on the merits of the order itself.⁸

Tariffs Under the International Emergency Economic Powers Act

On February 20, 2026, the Supreme Court held 6-3 in Learning Resources, Inc. v. Trump that the International Emergency Economic Powers Act does not authorize the president to impose tariffs. Chief Justice John Roberts wrote the majority opinion, joined on the core holding by Justices Sotomayor, Kagan, Gorsuch, Barrett, and Jackson. Roberts emphasized that tariffs are a form of taxation and that Article I vests the taxing power in Congress.⁹

A three-justice plurality of Roberts, Gorsuch, and Barrett applied the major questions doctrine, concluding that Congress would not have delegated a “highly consequential” power to impose unbounded unilateral tariffs through IEEPA’s ambiguous language. The Court noted that no president had invoked IEEPA to impose tariffs in the half-century since its enactment until Trump did so. Justices Thomas and Kavanaugh, joined by Alito, dissented. The ruling did not establish a refund mechanism for tariffs already collected.¹⁰

Federalizing the National Guard

On December 23, 2025, the Supreme Court ruled 6-3 in Trump v. Illinois that the president likely lacked authority to federalize National Guard troops for deployment to Chicago as part of an immigration enforcement campaign called “Operation Midway Blitz.” The unsigned majority opinion held that 10 U.S.C. § 12406(3) requires the president to first demonstrate that he is “unable” to execute federal laws using active-duty military forces. Because the Posse Comitatus Act restricts the military from executing domestic laws without specific authorization, and the government could not identify such authorization, the majority found the threshold unmet.¹¹

The majority also rejected the argument that courts could not second-guess the president’s military judgments, noting that political opposition does not constitute “rebellion” under the statute. Justices Alito, Thomas, and Gorsuch dissented. After the ruling, Trump announced the withdrawal of federalized National Guard forces from Chicago, Los Angeles, and Portland.¹²

Executive Orders Sanctioning Law Firms

The administration issued orders imposing sanctions on Perkins Coie, Jenner & Block, WilmerHale, Susman Godfrey, and other major firms, directing revocation of security clearances, suspension of government contracts, and the barring of firm attorneys from government buildings. Each firm sued.

In Perkins Coie LLP v. Department of Justice, Judge Beryl Howell granted summary judgment on May 2, 2025, ruling Executive Order 14230 unconstitutional under the First, Fifth, and Sixth Amendments and issuing a permanent injunction. Three weeks later, in Jenner & Block v. Department of Justice, Judge John Bates granted summary judgment, declaring Executive Order 14246 “null and void” for violating the First Amendment. Multiple district judges described the orders as “clear viewpoint discrimination.”⁴¹³

The government appealed. At consolidated oral arguments before the D.C. Circuit on May 14, 2026, the panel appeared skeptical of the argument that the sanctions were unreviewable national security decisions. A ruling has not issued.¹³

Alien Enemies Act Deportations

The administration invoked the Alien Enemies Act of 1798 to deport Venezuelan nationals to a prison in El Salvador. In A.A.R.P. v. Trump, the Supreme Court intervened on May 16, 2025, with a per curiam opinion vacating a Fifth Circuit ruling that had dismissed the detainees’ appeal. The Court held that detainees must receive notice “within a reasonable time and in such a manner as will allow them to actually seek habeas relief” before removal, and that notice of roughly 24 hours with no information on how to contest the action is constitutionally inadequate.¹⁴

Federal Funding Freeze

In late January 2025, the Office of Management and Budget ordered a “temporary pause” on nearly all federal financial assistance, affecting programs ranging from FEMA disaster relief to K-12 education to the CDC. A coalition of 22 state attorneys general sued. On February 1, 2025, Judge John McConnell Jr. in Rhode Island issued a temporary restraining order, finding the freeze was “likely a violation of the Constitution and statutes of the United States” because the president cannot unilaterally halt spending Congress has committed.¹⁵

Two days later Judge Loren AliKhan in Washington, D.C., issued a parallel restraining order, finding that “both logic and record evidence” contradicted the government’s claim that the pauses were independent agency decisions.¹⁶ After agencies continued withholding funds, Judge McConnell found the administration had violated his order. On March 16, 2026, the First Circuit largely upheld the lower court’s order. The underlying claim rests on the Impoundment Control Act of 1974, which requires congressional approval before any deferral or rescission of appropriated funds.¹⁷

Gender Identity and LGBTQ+ Orders

Executive Order 14168, issued January 20, 2025, directed federal agencies to require government-issued identification to reflect a person’s sex at birth and characterized transgender identity as “false” and “corrosive.” Several challenges followed.

In PFLAG v. Trump, a federal judge in Maryland blocked the order on February 13, 2025, and issued a preliminary injunction on March 4, 2025, preventing the administration from withholding funds from medical providers offering gender-affirming care to minors. The case remains active before the Fourth Circuit.¹⁸

A separate passport challenge reached the Supreme Court. A Massachusetts district court had enjoined the State Department from enforcing the sex-at-birth policy, and the First Circuit declined to stay the injunction. On November 6, 2025, the Supreme Court in Trump v. Orr granted a stay, holding that the government was “likely to succeed on the merits” and that requiring passports to display sex at birth does not violate equal protection principles. The stay remains in effect while the appeal proceeds.¹⁹

In San Francisco AIDS Foundation v. Trump, Judge Jon Tigar of the Northern District of California issued a preliminary injunction on June 9, 2025, blocking provisions in three executive orders that sought to defund LGBTQ+ and HIV-serving nonprofits. The court found the orders likely violated the First and Fifth Amendments and the separation of powers, describing them as an effort to “censor constitutionally protected speech” and “weaponize congressionally appropriated funds.”²⁰

Diversity, Equity, and Inclusion Orders

Two orders signed on January 20 and 21, 2025, directed federal agencies to terminate “equity-related” grants and required grant recipients to certify that they do not promote DEI programs that violate federal law. A federal judge in Maryland issued a preliminary injunction, finding the orders unconstitutionally vague and likely to chill protected speech.²¹

On March 14, 2025, the Fourth Circuit unanimously stayed that injunction and allowed enforcement to proceed while litigation continued, without ruling on the orders’ underlying legality. In a concurrence, Judge Pamela Harris noted that enforcement actions exceeding the orders’ “narrow scope” could still raise “serious First Amendment and Due Process concerns.”²¹

Federal Elections

A March 25, 2025, executive order directed the Election Assistance Commission to require documentary proof of citizenship when registering to vote through the national mail voter registration form. The League of Women Voters and other voting rights organizations sued, arguing the order violated the National Voter Registration Act and exceeded presidential authority. A federal judge issued a preliminary injunction on April 24, 2025, and on October 31, 2025, granted summary judgment and issued a permanent injunction. The court ruled that the president has no role in prescribing federal election regulations beyond signing or vetoing legislation and lacks authority over the independent Election Assistance Commission.²²

A second order, issued in March 2026, directed federal agencies to compile citizen lists and instructed the U.S. Postal Service to refuse ballots from voters not on a federally created list. The ACLU challenged the order in League of Women Voters of Massachusetts v. Trump, calling it an unconstitutional attempt to seize control of election administration from Congress and the states. That case remains ongoing.²³

Federal Employee Reclassification

On June 3, 2026, Trump signed an executive order creating “Schedule Policy/Career,” a new classification that strips civil service protections from roughly 8,000 career federal employees, primarily at the GS-15 level and above. Affected employees cannot appeal adverse actions to the Merit Systems Protection Board or challenge their reclassification. The order builds on the first-term “Schedule F” concept, which was largely unimplemented and later rescinded by the Biden administration.²⁴

A coalition of federal employee unions, including the American Federation of Government Employees, filed Peer v. Trump in the District of Maryland, arguing that the reclassification exceeds presidential authority, violates federal civil service laws, and unconstitutionally deprives workers of due process. The case remains pending.²⁵

What CASA Changed About Blocking Executive Orders

A ruling that an executive order is unconstitutional no longer automatically stops it everywhere. In Trump v. CASA, Inc., decided June 27, 2025, the Supreme Court held 6-3 that “universal injunctions likely exceed the equitable authority that Congress has granted to federal courts.” Justice Amy Coney Barrett’s majority opinion traced federal equity jurisdiction to the Judiciary Act of 1789 and found no historical basis for orders restraining the government’s treatment of non-parties. Justices Sotomayor, Kagan, and Jackson dissented.²⁶

The practical result is that relief must be tailored to the plaintiffs who demonstrate standing. The same executive order can remain in effect against some people while blocked for others. Class actions such as Barbara v. Trump are a response, attempting to use conventional class-action procedures to secure functionally broad protection.²⁷

Where the Government Has Prevailed

Not every challenge has succeeded. The government has won 126 of the 803 tracked cases, including 28 dismissed or decided on the merits in its favor.⁴ The Fourth Circuit allowed enforcement of the DEI orders to proceed. The Supreme Court stayed the injunction against the passport sex-designation policy in Trump v. Orr, finding the government likely to succeed on the merits.¹⁹ And the end of nationwide injunctions in Trump v. CASA was itself a significant procedural win, even though it left the constitutional questions in the birthright citizenship fight unresolved.

As of mid-2026, 360 cases remain awaiting a ruling, and the Supreme Court has not yet decided Barbara v. Trump, the class action that could produce the most consequential ruling on executive authority and constitutional citizenship in more than a century.⁸

1
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2
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3
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4
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SCOTUSblog. Supreme Court Sides With Trump Administration on Nationwide Injunctions in Birthright Citizenship Case
7
ACLU of New Hampshire. Federal Appeals Court Upholds Block on Trump Birthright Citizenship Executive Order
8
SCOTUSblog. Trump v. Barbara
9
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10
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11
Just Security. Trump v. Illinois: Supreme Court
12
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13
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14
Justia. A.A.R.P. v. Trump, 605 U.S. ___
15
ABC News. Trump Administration Funding Freeze Blocked by Federal Judge
16
ProPublica. Trump Administration Funding Freeze Workarounds
17
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18
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19
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20
Courthouse News Service. Judge Partially Blocks Trump’s Anti-DEI Executive Orders
21
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22
Brennan Center for Justice. The President’s Executive Order on Elections, Explained
23
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24
Federal News Network. Trump Moves About 8,000 Federal Positions to Schedule Policy/Career
25
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27
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