Controversial Executive Orders: Landmark Cases and Trump-Era Litigation

Controversial executive orders are the presidential directives that have drawn the fiercest court challenges and public backlash, from Franklin Roosevelt’s wartime internment of Japanese Americans to Harry Truman’s seizure of the steel mills, Richard Nixon’s freeze on wages and prices, Barack Obama’s DACA program, and the historic volume of orders issued in Donald Trump’s second term. What makes them controversial is almost always the same question: did the president act within the authority the Constitution and Congress have given the office, or beyond it? The answers have shaped landmark Supreme Court rulings, produced formal congressional apologies decades after the fact, and continue to reshape the boundaries of executive power today.

What an Executive Order Can and Cannot Do

The Constitution does not mention executive orders by name. Presidents claim authority to issue them from Article II, Section 1, which vests “the Executive Power” in the president, and from Sections 3 and 4, which require the president to “take Care that the Laws be faithfully executed.”¹ An executive order is a written directive that manages federal government operations. It carries the force of law and is codified under Title 3 of the Code of Federal Regulations. But it is not legislation. It cannot override federal statutes, create new laws, or appropriate money.²

Three checks apply. Congress can pass legislation that makes an order difficult or impossible to carry out, including by withholding funding. A sitting president can revoke a predecessor’s orders by issuing new ones. And federal courts can invalidate orders they find unconstitutional or beyond the president’s statutory authority.³ The third check is where most of the controversy lives.

The Youngstown Framework

Every major legal fight over an executive order runs through Youngstown Sheet & Tube Co. v. Sawyer, decided by the Supreme Court in 1952. During the Korean War, President Truman issued Executive Order 10340 to seize private steel mills and head off a labor strike he said would disrupt wartime production. The Court struck down the order 6-3, holding that the president lacks inherent constitutional power to seize private property without authorization from Congress.⁴

Justice Robert Jackson’s concurring opinion set out the three-tier framework courts still use. Presidential power is at its maximum when the president acts with the express or implied backing of Congress. It enters a “zone of twilight” when Congress has been silent, and the president relies on independent constitutional powers. It sits at its lowest ebb when the president acts against the expressed or implied will of Congress, and can rely only on whatever constitutional powers remain after subtracting Congress’s own authority.⁵ The Court found Truman’s steel seizure fell in the third category because Congress had considered and declined to grant such authority.⁶

Executive Order 9066 and Japanese American Internment

No executive order in American history is more widely condemned in retrospect than Executive Order 9066. President Roosevelt signed it on February 19, 1942. The order authorized military commanders to designate “military areas” and exclude any persons from them. Though its language was race-neutral, it was used to force the removal and incarceration of roughly 120,000 Japanese Americans from the West Coast. About two-thirds were U.S.-born citizens.⁷

Detainees were held in ten camps across remote areas of California, Arizona, Wyoming, Colorado, Utah, Idaho, and Arkansas, under armed guard. Citizens had to abandon homes, businesses, and property, often selling at a fraction of value. Congress reinforced the order by passing Public Law 503, making violation punishable by up to a year in prison and a $5,000 fine.⁷

In Korematsu v. United States (1944), the Supreme Court upheld the exclusion orders 6-3. Justice Hugo Black’s majority opinion held that while racial restrictions demand “rigid scrutiny,” they could be justified by “pressing public necessity” in wartime. Justice Frank Murphy dissented, calling the order a descent “into the ugly abyss of racism.” Justice Robert Jackson warned the ruling would validate racial discrimination in criminal procedure indefinitely.⁸ In 2011, the U.S. solicitor general confirmed that the government had withheld a Naval Intelligence report concluding Japanese Americans posed no threat, meaning the government had given the Court false information during the original proceedings.⁹

Repudiation came slowly. President Gerald Ford formally rescinded the order in 1976, stating, “We now know what we should have known then—not only was that evacuation wrong, but Japanese Americans were and are loyal Americans.”⁹ Federal courts overturned Fred Korematsu’s conviction in 1983. In 1988, Congress passed the Civil Liberties Act, issuing a formal apology and awarding $20,000 in restitution to each surviving internee.⁷ The Supreme Court’s 2018 decision in Trump v. Hawaii explicitly repudiated Korematsu as legal precedent.⁸

Executive Order 6102 and the Gold Seizure

On April 5, 1933, in the depths of the Great Depression, President Roosevelt signed Executive Order 6102. It required individuals, partnerships, and corporations to surrender their gold coin, gold bullion, and gold certificates to a Federal Reserve Bank by May 1, 1933. Banks paid an equivalent amount in other U.S. currency. Roosevelt issued the order under the Trading with the Enemy Act of 1917, as amended, during a declared national banking emergency.¹⁰

Exemptions covered gold used in industry or the arts, coins of recognized collector value, and holdings under $100 per person. Willful violations carried fines up to $10,000, imprisonment up to ten years, or both. The order defined “hoarding” broadly, as the “withdrawal and withholding of gold coin, gold bullion or gold certificates from the recognized and customary channels of trade.”¹⁰ It remains a touchstone for critics of expansive federal monetary authority, who view it as one of the most dramatic peacetime seizures of private assets by executive fiat.

Executive Order 9981 and Military Desegregation

Not every controversial order is remembered as a mistake. On July 26, 1948, President Truman signed Executive Order 9981, declaring “there shall be equality of treatment and opportunity for all persons in the armed services without regard to race, color, religion or national origin.”¹¹ It ended 170 years of formal military segregation and stands as one of the earliest uses of executive power to advance civil rights.

Truman turned to executive action because Congress would not act. When he asked Congress to enact civil rights legislation earlier in 1948, Southern senators threatened a filibuster and the proposals stalled.¹¹ Using his authority as commander in chief, Truman bypassed the legislature. Resistance was fierce. Secretary of the Army Kenneth Royall argued that “the Army is not an instrument for social evolution,” and Truman eventually forced him into retirement for refusing to comply. Conservative Southern Democrats walked out of the 1948 Democratic National Convention in protest. Integration was effectively completed in late 1954.¹²

Executive Order 11615 and Nixon’s Wage and Price Controls

On August 15, 1971, President Nixon signed Executive Order 11615, imposing a 90-day freeze on all prices, rents, wages, and salaries in the United States. The order rested on the Economic Stabilization Act of 1970, which Congress had passed partly as a political challenge, expecting the president would never actually use the authority.¹³

Markets rallied. Seventy-five percent of the public initially supported the plan. The controls quickly became a cautionary tale. After the initial freeze, price and wage increases required approval from a newly created Pay Board and Price Commission. A second freeze followed in June 1973. Distortions accumulated: ranchers withheld cattle from market, farmers destroyed poultry, and supermarket shelves emptied. Economist Milton Friedman called the program an “utter failure” that produced “suppressed inflation.” When controls were finally lifted, the wholesale price index spiked at an annual rate of 37 percent over the following three months.¹⁴ Gasoline controls, compounded by the 1973 Arab oil embargo, contributed to the gas lines of the late 1970s.

DACA and the Limits of Immigration by Executive Action

In June 2012, the Obama administration created the Deferred Action for Childhood Arrivals program through a Department of Homeland Security memorandum. DACA granted temporary relief from deportation and work authorization to unauthorized immigrants who had arrived in the United States as children. About 700,000 people participated.¹⁵

In November 2014, the administration tried to expand DACA and add a parallel program, Deferred Action for Parents of Americans (DAPA), which would have covered an estimated 4.3 million more people. Texas and 25 other states sued. A federal district court issued a preliminary injunction, the Fifth Circuit upheld it, and the Supreme Court affirmed by a 4-4 split in June 2016. The split carried no precedential weight but left the lower court ruling in place.¹⁶

When the Trump administration moved to rescind DACA in 2017, that decision was itself challenged. In DHS v. Regents of the University of California (2020), the Supreme Court ruled that the rescission was “arbitrary and capricious” under the Administrative Procedure Act because the administration had failed to adequately explain its reasoning or account for the reliance interests of DACA recipients. The Court did not rule on whether DACA itself was lawful.¹⁵ As of 2026, DACA’s legal status remains contested. The Fifth Circuit affirmed a lower court ruling in January 2025 that the program is unlawful, though current recipients continue to receive renewals while the matter proceeds in district court.¹⁶

Trump’s Second Term: A Historic Volume of Litigation

The second term of President Trump, which began in January 2025, has produced an extraordinary volume of executive orders and an equally extraordinary volume of legal challenges. As of June 2026, the Just Security Litigation Tracker has identified 803 separate lawsuits against the administration’s executive actions.¹⁷ According to Harvard’s Kennedy School, nearly 30 percent of the executive orders issued in the first 100 days were challenged in court.¹⁴ The orders span immigration, voting rights, DEI policy, the federal workforce, funding freezes, and sanctions against law firms.

Birthright Citizenship

On January 20, 2025, Trump signed Executive Order 14160, directing federal agencies to stop issuing documents recognizing U.S. citizenship to children born in the country if neither parent is a citizen or lawful permanent resident.¹⁸ The order advanced a novel interpretation of the Fourteenth Amendment’s guarantee of citizenship to all persons “born or naturalized in the United States, and subject to the jurisdiction thereof.”

Multiple federal courts blocked the order. In July 2025, a Ninth Circuit panel ruled it “invalid because it contradicts the plain language of the Fourteenth Amendment’s grant of citizenship.” A New Hampshire district court issued a preliminary injunction the same month, finding the order likely “contradicts the text of the Fourteenth Amendment and the century-old untouched precedent that interprets it,” referring to the Supreme Court’s 1898 ruling in United States v. Wong Kim Ark.¹⁹ The Supreme Court agreed to hear the case in December 2025, with oral arguments scheduled for April 1, 2026, and a ruling expected by late June or early July 2026.²⁰

DEI Programs

On January 20 and 21, 2025, the administration issued two executive orders aimed at dismantling diversity, equity, and inclusion initiatives. Executive Order 14151 directed agencies to terminate all DEI offices, positions, equity action plans, and related grants or contracts within 60 days.²¹ Executive Order 14173 went further, requiring federal contractors and grantees to certify that they do not operate programs “promoting DEI” that violate federal anti-discrimination laws, and designating that certification as material to government payment decisions under the False Claims Act.²²

In Chicago Women in Trades v. Trump, Judge Matthew Kennelly of the Northern District of Illinois granted a preliminary injunction in April 2025 blocking enforcement of the certification provision on First Amendment grounds. In October 2025, he declined to narrow the injunction. The government appealed to the Seventh Circuit.²³ In National Association of Diversity Officers in Higher Education v. Trump, the Fourth Circuit vacated a preliminary injunction in February 2026, holding that the plaintiffs had brought only “facial challenges” and were unlikely to succeed, though it left the door open for future “as-applied” challenges.¹⁷

Federal Grant and Loan Freezes

On January 20, 2025, the president signed an executive order pausing disbursement of funding under the Inflation Reduction Act and the Infrastructure Investment and Jobs Act, pending review. On January 27, the Office of Management and Budget issued a broader directive pausing grant, loan, and other financial assistance programs government-wide, then rescinded that directive two days later.²⁴

The freeze persisted in practice. U.S. District Judge John McConnell of Rhode Island issued a temporary restraining order on January 31, 2025, requiring the administration to unfreeze the funds. When plaintiffs reported the funds were still inaccessible, the administration argued it was complying with its own interpretation of the court’s “ambiguous” order. Judge McConnell rejected that on February 10, ruling the administration had violated the “plain language” of his “clear and unambiguous” order, and threatened criminal contempt.²⁵ On February 25, Judge Loren AliKhan indefinitely blocked the funding freeze.²⁴

Travel Bans

Beginning with Executive Order 14161 on January 20, 2025, the administration pursued broad travel restrictions. A June 4, 2025, proclamation imposed full entry bans on nationals of 12 countries and partial bans on seven more.²⁶ A December 2025 proclamation expanded the restrictions to 34 countries with full or partial suspensions, targeting nations over vetting deficiencies, high visa overstay rates, and refusal to accept deported nationals.²⁷

Unlike the 2017 travel bans, which triggered immediate mass protests and rapid court injunctions, the 2025 version was structured with categorical exemptions for lawful permanent residents, dual nationals, immediate relatives of U.S. citizens, and refugees. Analysts noted the exemptions made it harder to challenge in court, and the response from the public and the courts was described as “notably subdued” compared with the first term.²⁶

Sanctions on Law Firms

In March 2025, the administration issued executive orders imposing sanctions on several major law firms, including terminating government contracts, suspending security clearances, and restricting building access. The targeted firms challenged the orders and won at trial. On May 2, 2025, Judge Beryl Howell declared Executive Order 14230 (targeting Perkins Coie) unconstitutional, finding violations of the First, Fifth, and Sixth Amendments, and permanently enjoined its enforcement. On May 23, Judge John Bates declared Executive Order 14246 (targeting Jenner & Block) “null and void” as a First Amendment violation.¹⁷ The D.C. Circuit consolidated the appeals, with oral argument scheduled for May 14, 2026.

Voter Registration and Elections

Executive Order 14248, issued in March 2025, directed federal agencies to assess citizenship before providing voter registration forms to recipients of public assistance and required documentary proof of citizenship on federal absentee voting forms used by military servicemembers and overseas citizens. On January 30, 2026, Judge Colleen Kollar-Kotelly issued a 110-page opinion declaring those provisions “inconsistent with the constitutional separation of powers,” stating: “Our Constitution does not allow the president to impose unilateral changes to federal election procedures.”²⁸ An earlier October 2025 ruling by the same judge blocked a provision seeking to impose documentary proof-of-citizenship requirements on the national mail voter registration form.²⁹

Schedule Policy/Career

On June 3, 2026, the president signed Executive Order 14410, formally implementing the “Schedule Policy/Career” classification, reclassifying approximately 8,000 senior career federal employees as effectively at-will workers. The positions affected are primarily at or above the GS-15 level and include agency and division heads, chief information officers, regional officers, and personnel involved in writing regulations. Employees in this category can no longer challenge adverse personnel actions before the Merit Systems Protection Board, and their whistleblower complaints are investigated by their own agencies rather than the independent Office of Special Counsel.³⁰

The concept originated as “Schedule F” in a 2020 executive order, was rescinded under President Biden, and was revived through a new Office of Personnel Management rule that took effect in March 2026. Federal employee unions, including the American Federation of Government Employees, have filed lawsuits alleging the policy violates the Constitution, the 1978 Civil Service Reform Act, and the Administrative Procedure Act. The ACLU of the District of Columbia has characterized the order as a “power-grab” that threatens First Amendment rights by allowing retaliation based on employees’ political activities and donations.³¹ Administration officials have countered that the policy involves “zero loyalty tests” and is designed to ensure career staff are capable of carrying out lawful directives.³⁰

Mass Rescission of Prior Orders

On January 20, 2025, Trump signed an order rescinding more than 70 Biden-era executive actions covering racial equity, DEI, climate policy, COVID-19 response, immigration enforcement, LGBTQI+ protections, and voter access. A second order on March 14, 2025, revoked 18 additional actions. The administration characterized the rescinded policies as “deeply unpopular, inflationary, illegal, and radical.”³² The White House stated that within two months, Trump had rescinded more executive actions than Biden had signed during his entire first year.³³

Trump v. CASA and the End of Nationwide Injunctions

One of the most structurally significant developments in executive order litigation came not from a policy dispute but from a procedural ruling. On June 27, 2025, the Supreme Court decided Trump v. CASA, Inc. in a 6-3 opinion authored by Justice Amy Coney Barrett. The Court held that federal courts lack statutory authority under the Judiciary Act of 1789 to issue “universal” or “nationwide” injunctions that block a government policy against everyone, not just the plaintiffs before the court.³⁴

The majority reasoned that English equity practice at the time of the founding recognized only party-specific remedies, and that “complete relief” means complete relief between the parties, not relief for everyone affected by a policy. Justice Sotomayor dissented, joined by Justices Kagan and Jackson.³⁴ The practical effect has been large. Lower courts reviewing the birthright citizenship order and other challenged policies had to narrow their injunctions to cover only specific plaintiffs and states, letting the administration enforce contested orders against anyone not specifically protected by a court ruling.²⁰

Other Supreme Court Rulings on Second-Term Executive Power

Beyond CASA, the Supreme Court’s emergency docket in 2025 produced several other significant rulings:

In A.A.R.P. v. Trump, the Court blocked the administration from using the Alien Enemies Act of 1798 to deport individuals to a maximum-security prison in El Salvador and remanded the case to the Fifth Circuit to evaluate whether the act’s requirements were met.³⁵
In Trump v. Illinois, the Court ruled 6-3 in December 2025 that the administration failed to identify legal authority to federalize the Illinois National Guard over the governor’s objection to respond to unrest at immigration facilities near Chicago. The majority found the administration had not explained why the situation justified an exception to the Posse Comitatus Act.³⁶
In a pair of 5-4 decisions on federal funding disputes, the Court stayed lower court orders that had blocked termination of NIH grants and Department of Education grants, ruling that such contract-based disputes belong in the Court of Federal Claims rather than district court. It denied a stay in a State Department case, allowing an order requiring $2 billion in reimbursements to nonprofits to remain in effect.³⁷

Taken together, these cases have produced a rapid feedback loop between aggressive executive action and judicial response. With the birthright citizenship case headed for a merits ruling by mid-2026 and dozens of other challenges moving through the appellate courts, the legal boundaries of executive orders remain in active flux.

1
American Bar Association. Executive Orders
2
American Bar Association. What Is an Executive Order
3
ACLU. What Is an Executive Order and How Does It Work
4
Justia. Youngstown Sheet and Tube Co. v. Sawyer
5
National Constitution Center. Youngstown Sheet and Tube Co. v. Sawyer
6
Federal Judicial Center. Judicial Review of Executive Orders
7
National Archives. Executive Order 9066
8
National Constitution Center. A Controversial Order Leads to Internment Camps
9
Britannica. The Legacy of Order 9066 and Japanese American Internment
10
UC Santa Barbara American Presidency Project. Executive Order 6102
11
National Archives. Executive Order 9981
12
History.com. Harry Truman Executive Order 9981
13
UC Santa Barbara American Presidency Project. Executive Order 11615
14
Harvard Kennedy School. Explainer: Executive Orders as a Governing Tool
15
U.S. Supreme Court. DHS v. Regents of the University of California
16
Congressional Research Service. Deferred Action for Childhood Arrivals
17
Just Security. Tracker: Litigation and Legal Challenges to the Trump Administration
18
The White House. Protecting the Meaning and Value of American Citizenship
19
SCOTUSblog. Trump Urges Supreme Court to Decide Whether to End Birthright Citizenship
20
Brennan Center for Justice. Birthright Citizenship Under the U.S. Constitution
21
Federal Register. Ending Radical and Wasteful Government DEI Programs and Preferencing
22
Illinois Attorney General. Amicus Brief in CWIT v. Trump
23
Civil Rights Litigation Clearinghouse. Chicago Women in Trades v. Trump
24
Columbia Law School Sabin Center for Climate Change Law. Trump Administration Freezes Billions of Dollars in Federal Grants and Loans
25
National Conference of State Legislatures. NCSL Updates on Federal Funding Pause
26
American Immigration Council. Trump 2025 Travel Ban
27
The White House. Restricting and Limiting the Entry of Foreign Nationals
28
Courthouse News Service. Federal Judge Blocks Trumps New Voter Registration Requirements
29
Elias Law Group. Federal Court Permanently Blocks Additional Provisions of Executive Order on Elections
30
Government Executive. Trump Moves Federal Employees to Schedule Policy Career
31
ACLU-DC. ACLU-DC Responds to Executive Order on Schedule Policy/Career Federal Workers
32
The White House. Initial Rescissions of Harmful Executive Orders and Actions
33
The White House. Fact Sheet: President Donald J. Trump Rescinds Additional Harmful Biden Executive Actions
34
U.S. Supreme Court. Trump v. CASA, Inc.
35
U.S. Supreme Court. A.A.R.P. v. Trump
36
NPR. Supreme Court Chicago National Guard
37
SCOTUSblog. Looking Back at 2025: The Supreme Court and the Trump Administration