July 23, 2025 – As of May 2025, executive orders are at the forefront of American political and legal dialogue.
During the first four months of his second term, President Donald Trump has issued a slew of executive orders – resulting in a slew of court challenges, most of them still pending at the time this article was written. But most Americans – indeed, most lawyers – know very little about the history of executive orders and appear to consider them a recent development.
Actually, the use of executive orders dates to George Washington’s first term. And their peak usage as a tool of presidential power came during the early and middle portions of the 20th century – not under recent administrations.
Executive orders range from the benign to the controversial. Their potential to encroach on legislative power results in complicated legal analysis in determining their validity. These are weighty questions – the Founders considered separation of powers essential to the survival of the republic.[1]
This article briefly examines the history and use of executive orders, discusses successful court challenges to them, and provides the basic framework and general rules by which courts determine the validity of any particular executive order.
At the time this article was drafted, hundreds of lawsuits were pending across the country challenging executive orders issued by President Trump during his first few months in office. Almost all of those challenges were ongoing. The legal landscape was changing almost daily. As a result, those cases are beyond the scope of this article.
For those interested in tracking the various legal challenges, several of the nation’s largest law firms have dedicated a portion of their respective websites to tracking the progress of the various lawsuits challenging these executive orders.
Presidential Executive Orders: A Very Brief History
In 1793, George Washington issued a proclamation that the United States would remain neutral in the most recent outbreak of hostilities between Britain and France.[2]
Chad Baruch, a member of the State Bar’s Nonresident Lawyer Division and Appellate Practice Section, is with
Johnston, Tobey, and Baruch in Dallas. His practice focuses on civil and family appeals, constitutional law, legal ethics, and representation of judges before the State Commission on Judicial Conduct. He is Board Certified in Civil Appellate Law by the Texas Board of Legal Specialization.
James Madison criticized Washington’s proclamation as infringing on Congress’s authority to decide issues of war and peace. But Congress ratified it by passing the Neutrality Act of 1794, giving the president power to prosecute violators of the proclamation.[3]
In 1794, Washington issued a proclamation ordering participants in the Whiskey Rebellion to disperse and activating the militia to put down the rebellion. He acted under a statute requiring him to warn citizens to disperse but then permitting him to mobilize the militia in response to any who refused to comply.[4]
President Abraham Lincoln used presidential directives extensively during the early months of the Civil War. He used proclamations to mobilize troops, force Congress to convene, procure warships, and expand the military.[5]
Lincoln’s successor, President Andrew Johnson, issued the “Christmas Proclamation” pardoning “all and every person who directly or indirectly participated in the late insurrection or rebellion” related to the Civil War.[6] He did so under his constitutional pardon power. The Supreme Court confirmed the proclamation’s validity.[7]
President Franklin Roosevelt (FDR) greatly expanded the use of executive orders, partly in response to the growth of government and largely due to World War II.[8]
FDR used executive orders for a wide range of activities, including relocation of people of Japanese descent, creation of the National Labor Relations Board, and implementation of the National Industrial Recovery Act.[9]
FDR’s successor, President Harry Truman, became the first president to have an executive order overturned in its entirety as a result of his effort to take control of most of the country’s steel mills.[10] “Presidents since the time of Truman have generally maintained an expansive view of presidential power and have used this power to implement policy, even when the orders have been somewhat controversial.”[11] Beginning with President John F. Kennedy, every successive president has issued controversial executive orders.[12]
Presidential Proclamations and Executive Orders by the Numbers
Here are the top 10 presidents in terms of number of executive orders issued:[13]
Franklin D. Roosevelt (D) 3,726
Woodrow Wilson (D) 1,803
Calvin Coolidge (R) 1,203
Theodore Roosevelt (R) 1,081
Herbert Hoover (R) 1,003
Harry S. Truman (D) 907
William Howard Taft (R) 724
Warren G. Harding (R) 522
Dwight D. Eisenhower (R) 484
Ronald Reagan (R) 381
Here are a few others you may find interesting:
Separation of Powers and Executive Orders 2025
In the first 100 days of his second term, President Donald Trump signed over 140 executive orders – more than any other modern president in the same timeframe. While this uptick has garnered attention, previous administrations have also faced scrutiny for their use of executive orders, including Presidents Barack Obama and Joe Biden. But how do executive orders fit into the U.S. legal landscape of legislation, regulation, and case law?
Gain a better understanding of the issues at play with
Separation of Powers and Executive Orders from State Bar of Wisconsin PINNACLE. This 1.0 CLE program is available on select days
by webcast through August 25, 2025, and
as an OnDemand seminar viewable at your convenience.
In this program, veteran constitutional lawyers Chad Baruch and David Coale discuss:
- the historical purpose and constitutional basis for executive orders;
- how various administrations have used executive orders;
- notable executive orders issued so far in 2025; and
- how the courts and Congress act as checks on executive power.
Attorneys from a range of practice areas – from administrative to immigration law – may encounter legal or policy shifts tied to executive actions. Separation of Powers and Executive Orders provides a framework for understanding the balance of powers in today’s government and the legal mechanisms designed to protect it.
Find out more on WisBar’s Marketplace
Youngstown: The Template for Evaluating Executive Orders
In 1951, a dispute erupted between steel companies and employees over terms and conditions of employment. After federal attempts to encourage settlement collapsed, the United Steelworkers gave notice for a strike.
President Truman – concerned about the national supply of steel for war materials – issued an executive order authorizing the Secretary of Commerce to take possession of most steel mills to ensure their continued operation. Mill owners sued, arguing this order exceeded presidential authority. The Supreme Court agreed and upheld the district court ruling striking down the order.
Writing for the majority, Justice Hugo Black noted “[t]he President’s power, if any, to issue the order must stem either from an act of Congress or from the Constitution itself.”[14]
Although no express constitutional or congressional grant of authority existed, President Truman justified his action under an implied grant of power based on three Constitutional provisions:
(1) “[t]he executive Power shall be vested in a President of the United States of America,” U.S. Const. art. II, § 1, cl. 1;
(2) the President “shall take Care that the Laws be faithfully executed,” U.S. Const. art. II, § 3; and
(3) the President’s power as Commander in Chief. U.S. Const. art. II, § 2, cl. 1.
The Court first addressed the commander-in-chief argument, holding this power did not support “tak[ing] possession of private property in order to keep labor disputes from stopping production.” The Court then rejected Truman’s other arguments based on both the framework and language of the Constitution. Ultimately, the Court deemed the president the “executor” of the laws rather than the “lawmaker.”[15]
But the most influential opinion in
Youngstown wasn’t Black’s majority opinion. Instead, it was the concurring opinion written by Justice Robert Jackson. It contains the most thorough discussion of the issue and is the most frequently cited of the opinions in the case. Indeed, it is considered the seminal opinion concerning the validity of executive orders.[16] Justice Jackson outlined three areas of presidential authority:
(1) When the president acts pursuant to an express or implied authorization of Congress, his authority is at its maximum, for it includes all that he possesses in his own right plus all that Congress can delegate.
(2) When the president acts in absence of either a congressional grant or denial of authority, he can only rely upon his own independent powers, but there is a zone of twilight in which he and Congress may have concurrent authority, or in which its distribution is uncertain. Therefore, congressional inertia, indifference or quiescence may sometimes, at least as a practical matter, enable, if not invite, measures on independent presidential responsibility.
(3) When the president takes measures incompatible with the expressed or implied will of Congress, his power is at its lowest ebb, for then he can rely only upon his own constitutional powers minus any constitutional powers of Congress over the matter.[17]
Even today, Justice Jackson’s discussion of these three categories and the scope of presidential power entailed by each remains the touchstone for judicial analysis of executive orders.
Only a few circuit decisions have struck down executive orders. The Fourth Circuit did so in
Liberty Mutual Insurance Co. v. Friedman.[18] There, insurance companies challenged a determination by the Director of the Office of Federal Contract Compliance Programs deeming them subcontractors within the meaning of a previous executive order.
The Fourth Circuit held the companies were subcontractors within the meaning of the regulations. But it held that “application of the Executive Order to plaintiffs is not reasonably within the contemplation of any statutory grant of authority.”[19]
In analyzing the extent of authority granted by Congress, the court assumed the order was based on the Procurement Act. But it held that government agents “acted outside any grant of legislative authority when they sought to impose the requirements of Executive Order 11,246 upon plaintiffs.” Even with a grant of statutory authority, that grant had to “reasonably contemplate” the regulations issued.[20]
In Ozonoff v. Berzak,[21] the plaintiff challenged an executive order requiring American citizens to pass a “loyalty” review before entering employment for any international organization. The court found the order unconstitutionally broad under the First Amendment, or at least unlawful when applied to an applicant with the World Health Organization.[22]
In
Chamber of Commerce v. Reich,[23] President Bill Clinton signed an executive order saying, “contracting agencies shall not contract with employers that permanently replace lawfully striking employees.” When the Secretary of Labor issued regulations implementing it, the Chamber of Commerce sought declaratory and injunctive relief against their enforcement arguing the order violated the Procurement Act (on which it was based) and the National Labor Relations Act (NLRA). The court concluded the order conflicted with and was preempted by the NLRA.[24]
Finally, the Ninth Circuit considered executive orders by President Trump in
San Francisco v. Trump.[25] The orders at issue required authorities to withhold federal funds from “sanctuary cities” that did not share immigration and citizenship information with the federal government.
Citing Justice Jackson’s test in
Youngstown, the Ninth Circuit held that “because Congress has the exclusive power to spend and has not delegated authority to the Executive to condition new grants on compliance with § 1373, the President’s ‘power is at its lowest ebb.’”
The court concluded that under the constitutional principle of separation of powers and in light of the Spending Clause (vesting exclusive power in Congress to impose conditions on federal grants), the executive branch may not refuse to disperse federal grants without congressional authorization.[26] The case was appealed to the Supreme Court but vacated when Joe Biden became president.
Conclusion: Analyzing the Validity of Future Executive Orders
As the foregoing cases make clear, deciding the validity of any particular executive order may not always be simple. Read cumulatively, though, the decisions suggest that executive orders are likely to be invalidated when they:
rely solely on inherent Constitutional authority;
are based on a Congressional grant but exceed the scope of that grant of authority;
violate the Constitution;
violate or contradict a statute;
are preempted by statute; or
exercise a power reserved exclusively to Congress.
Endnotes
[1]
See
The Federalist No. 51, at 355-59 (James Madison) (Benjamin Fletcher Wright ed., 1961);
see also generally Carol Berkin,
A Brilliant Solution: Inventing the American Constitution 73 (2002).
[2]
See Joseph J. Ellis,
His Excellency George Washington 222 (2004);
see also Todd F. Gaziano,
The Use and Abuse of Executive Orders and Other Presidential Directives, 5 Tex. Rev. L. & Pol. 267, 273-75 (2001).
[3]
See Gaziano,
supra note 2, at 275.
[4] By the President of the United States of America: A Proclamation (Aug. 7, 1794),
reprinted in 1
Messages and Papers of the Presidents: 1789-1897, at 158-60.
[5]
See Jon Meacham,
And There Was Light: Abraham Lincoln and the American Struggle 243 (2022); Message to the Senate and House of Representatives from Abraham Lincoln (May 26, 1862),
reprinted in 6
Messages and Papers of the Presidents: 1789-1897, at 77; By the President of the United States: A Proclamation (May 3, 1861),
reprinted in 6
Messages and Papers of the Presidents: 1789-1897, at 15-16.
[6] By the President of the United States: A Proclamation (Dec. 25, 1868),
reprinted in 6
Messages and Papers of the Presidents: 1789-1897, at 708.
[7]
Armstrong v. United States, 80 U.S. (13 Wall.) 154, 156 (1871).
[8]
See Terry M. Moe & William G. Howell,
The Presidential Power of Unilateral Action, 15 J.L. Econ. & Org. 132, 155 (1999).
[9]
See H.W. Brands,
Traitor to His Class, 349–50, 462, 658, 756-57 (2008);
see also Tara Branum,
President or King? The Use and Abuse of Executive Orders in Modern-Day America, 28 J. Legis. 1, 28-29 (2002).
[10]
Youngstown Sheet & Tube Co. v. Sawyer, 343 U.S. 579, 589 (1952).
[11] Branum,
supra note 9, at 30.
[12]
See id. at 30-31.
[13]
The American President Project, Executive Orders (last visited July 17, 2025).
[14]
Youngstown, 343 U.S. at 585.
[15]
Id. at 587.
[16]
See Dames & Moore v. Regan, 453 U.S. 654, 661 (1981) (noting the concurrence “brings together as much combination of analysis and common sense as there is in this area”).
[17]
Youngstown, 343 U.S. at 635-37 (Jackson, J., concurring).
[18]
Liberty Mutual Insurance Co. v. Friedman, 639 F.2d 164 (4th Cir. 1991).
[19]
Id. at 166-68.
[20]
Id. at 169-72.
[21]
Ozonoff v. Berzak, 744 F.2d 224 (1st Cir. 1984).
[22]
Id. at 230-34.
[23]
Chamber of Commerce v. Reich, 74 F.3d 1322 (D.C. Cir. 1996).
[24]
Id. at 1324-25, 1338-39.
[25]
San Francisco v. Trump, 897 F.3d 1225 (9th Cir. 2018).
[26]
Id. at 1232-35.
