★
Executive Orders Historical Archive
Cite
Executive Order 14404 🏛️✅ Zone 1: Maximum Authority Constitutional Fidelity (+0.62) 📜 Art. II §2: Commander-in-Chief Supervisory Authority

Imposing Sanctions on Those Responsible for Repression in Cuba and for Threats to United States National Security and Foreign Policy

•
Friday, May 1, 2026
•
11 min read (2,232 words)
•
91 Fed. Reg. 25061

Executive Brief • At a Glance

⏱️ 11 min read (2,232 words) • ● In Effect
🎯 Primary Mandate

All property and interests in property that are in the United States, that hereafter come within the United States, or that are or hereafter come within the possession or control of any United States persons of the following persons are blocked and may not be transferred, paid, exported, withdrawn, or otherwise dealt in: (i) any foreign person determined by the Secretary of State, in consultation with the Secretary of the Treasury; or by the Secretary of the Treasury, in consultation with the Secretary of State: (A) to operate in or have operated in the energy, defense and related materiel, metals and mining, financial services, or security sector of the Cuban economy, or any other sector of the Cuban economy, as may be determined by the…

⚖️ Constitutional Footing
🏛️✅ Zone 1: Maximum Authority
Express or Implied Congressional Authorization
📜 Art. II §2: Commander-in-Chief Supervisory Authority
🏛️ Scope & Affected Sectors
Armed Forces & Military Establishments Sovereign State Governments & Localities Executive Departments & Federal Civil Servants Private Citizens & Property Owners

Plain-English Translation & Framers' Constitutional Analysis

Early Statesman synthesis distilling legal jargon into practical meaning, statutory anchors, and structural constitutional impacts.

Signed by President Donald Trump on May 1, 2026, this order concerns Imposing Sanctions on Those Responsible for Repression in Cuba and for Threats to United States National Security and Foreign Policy. I hereby determine and order: Section 1 . Policy. The policies, practices, and actions of the Government of Cuba, as described in Executive Order 14380 , continue to constitute an unusual and extraordinary threat, which has its source in whole or substantial part outside the United States, to the national security and foreign policy of the United States.

Constitutional Assessment: Scrutinized through Article II, Section 2, this action exercises the President's constitutional role as Commander in Chief. Early Framers recognized broad executive discretion in commanding military forces during conflict, provided it remains bounded by congressional declarations and respects civilian domestic courts.

Key Directives & Operative Actions

▪
Sanctionable Conduct

All property and interests in property that are in the United States, that hereafter come within the United States, or that are or hereafter come within the possession or control of any United States persons of the following persons are blocked and may not be transferred, paid, exported, withdrawn, or otherwise dealt in: (i) any foreign person determined by the Secretary of State, in consultation with the Secretary of the Treasury; or by the Secretary of the Treasury, in consultation with the Secretary of State: (A) to operate in or have operated in the energy, defense and related materiel, metals and mining, financial services, or security sector of the Cuban economy, or any other sector of the Cuban economy, as may be determined by the…

▪
Travel

I hereby find the unrestricted immigrant and nonimmigrant entry into the United States of aliens determined to meet one or more of the criteria in section 2(a)(i) of this order would be detrimental to the interests of the United States, and I hereby suspend entry into the United States, as immigrants or nonimmigrants, of such persons, except where the Secretary of State, or the Secretary of State's designee, determines that the person's entry is in the national interest of the United States.

▪
Foreign Financial Institutions

The Secretary of the Treasury, in consultation with the Secretary of State, is hereby authorized to impose on a foreign financial institution one or more of the sanctions described in subsection (b) of this section upon determining that the foreign financial institution has conducted or facilitated any significant transaction or transactions for or on behalf of any person whose property or interests in property are blocked pursuant to this order.

▪
Delegation

Consistent with applicable law, the Secretary of State and the Secretary of the Treasury are directed and authorized to take all actions necessary to implement and effectuate this order—including through temporary suspension or amendment of regulations or through notices in the Federal Register and by adopting rules, regulations, or guidance—and to employ all powers granted to the President, including by IEEPA, as may be necessary to implement this order.

Constitutional & Societal Entities Impacted

🏛️ Armed Forces & Military Establishments 🏛️ Sovereign State Governments & Localities 🏛️ Executive Departments & Federal Civil Servants 🏛️ Private Citizens & Property Owners 🏛️ Foreign Nations & International Entities
🏛️

The Framers' Constitutional Council

1787 Prism

Evaluating this order against the constitutional debates of 1787 and the limits of Article II executive power.

🏛️✅ Zone 1 (Maximum Authority)
§

"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."

— Justice Robert H. Jackson, Youngstown Sheet & Tube Co. v. Sawyer (1952) Express or Implied Congressional Authorization
JM

James Madison

Separation of Powers & Legislative Primacy

"The constitutional magistracy was designed not to invent policy, but to be the faithful instrument of the laws passed by the people's representatives." — Speech in the First Congress (1789)

Madison would approve the structural posture of this order. The President acts strictly in subordination to statutory authority granted under Article II, Section 3 ("take Care that the Laws be faithfully executed"). The checks and balances hold firm because the policy origin remains with the legislature.

Madisonian Stance: Concurring (Statutory)
AH

Alexander Hamilton

The Energetic Executive & Unified Command

"The direction of war implies the direction of the common strength; and the power of directing and employing the common strength must be under the direction of the single hand of the Executive." — Federalist No. 74 (1788)

Hamilton would forcefully champion executive discretion here. For foreign entanglements, commerce defense, and national security, deliberative assemblies are too slow and faction-ridden. A unified, energetic Executive exercising swift command is precisely what the Philadelphia Convention intended for national preservation.

Hamiltonian Stance: Strong Prerogative Support
GM

George Mason

Bill of Rights, Due Process & 10th Amendment

"The president will be surrounded by flatterers and sycophants... and the great powers of the executive will gradually absorb the liberties of the people." — Cato IV (Anti-Federalist, 1787)

The Anti-Federalist prism advises continuous democratic vigilance. Even routine administrative directives aggregate centralized federal power away from town halls and state assemblies toward a distant executive apparatus.

Anti-Federalist Stance: Eternal Vigilance Required
📐

Five Measurable "Constitutional Friction" Dimensions

An objective audit measuring potential separation-of-powers tension against the United States Constitution and established Supreme Court doctrine.

⚠️ Elevated Constitutional Friction
71 / 100 friction index
Dimension 1 • Art. I, §1 & §8

Legislative Encroachment & Purse

High Friction

Touches upon core congressional prerogatives: raises appropriations reallocation, tariff imposition, or statutory preemption questions.

Benchmark: Power of the purse, taxes/tariffs, and rule of law reserved to Congress.
Dimension 2 • Art. II, §1 & §3

Executive Scope & Faithfulness

High Friction

Invokes broad unilateral or emergency executive authorities that test the constitutional boundary of the Take Care Clause.

Benchmark: Faithfully execute laws enacted by Congress vs. unilateral decree.
Dimension 3 • 10th Amendment

Federalism & State Sovereignty

High Friction

Creates friction with the Tenth Amendment by conditioning state grants, mandating local compliance, or preempting state police powers.

Benchmark: Police powers and un-delegated responsibilities reserved to the States.
Dimension 4 • 5th & 14th Amendments

Due Process & Individual Rights

High Friction

Scrutinized under the Bill of Rights for potential impact on private contracts, property rights, or procedural due process.

Benchmark: Protection of private property, contracts, liberty, and procedural justice.
Dimension 5 • Separation of Powers

Youngstown Jacksonian Tier

Low Friction

The President operates strictly as the constitutional Chief Executive, carrying out policy established by Congress with strong statutory backing.

Benchmark: Express or Implied Congressional Authorization
⚖️ Audit Synthesis

This directive engages significant constitutional friction across statutory authorization, legislative prerogatives, or individual liberties.

Weighted composite: Art. I (25%), Art. II (25%), Federalism (15%), Due Process (15%), Youngstown (20%).
ℹ️
How to read these dimensions: Executive power expands whenever an administration acts without explicit statutory authorization from Congress (Article I), touches upon police powers historically reserved to the states (Tenth Amendment), or limits private rights and property without judicial process. A low friction score indicates strict concordance with enacted law; a high friction score highlights orders testing the limits of presidential discretion.
Total Words
2,232
13,774 characters
Estimated Read Time
11 min
@ 200 words / min
Flesch-Kincaid
28.6
Post-Graduate Legal
Language Tone Score
+0.62
Constitutional Fidelity
How is this scored?
Text size:

Official Archival Text

View Source Document

Executive Order 14404 of May 1, 2026 Imposing Sanctions on Those Responsible for Repression in Cuba and for Threats to United States National Security and Foreign Policy By the authority vested in me as President by the Constitution and the laws of the United States of America, including the International Emergency Economic Powers Act ( 50 U.S.C. 1701 et seq. ) (IEEPA), the National Emergencies Act ( 50 U.S.C. 1601 et seq. ) (NEA), section 212(f) of the Immigration and Nationality Act of 1952 ( 8 U.S.C. 1182(f) ), and section 301 of title 3, United States Code , and in order to take further steps with respect to the national emergency declared in Executive Order 14380 of January 29, 2026 (Addressing Threats to the United States by the Government of Cuba), I hereby determine and order:

Section 1 . #sec-1

Policy. The policies, practices, and actions of the Government of Cuba, as described in Executive Order 14380 , continue to constitute an unusual and extraordinary threat, which has its source in whole or substantial part outside the United States, to the national security and foreign policy of the United States. Not only are these policies, practices, and actions designed to harm the United States, but they are also repugnant to the moral and political values of free and democratic societies.

Sec. 2 . #sec-2

Sanctionable Conduct. (a) All property and interests in property that are in the United States, that hereafter come within the United States, or that are or hereafter come within the possession or control of any United States persons of the following persons are blocked and may not be transferred, paid, exported, withdrawn, or otherwise dealt in: (i) any foreign person determined by the Secretary of State, in consultation with the Secretary of the Treasury; or by the Secretary of the Treasury, in consultation with the Secretary of State: (A) to operate in or have operated in the energy, defense and related materiel, metals and mining, financial services, or security sector of the Cuban economy, or any other sector of the Cuban economy, as may be determined by the Secretary of the Treasury, in consultation with the Secretary of State; (B) to be owned, controlled, or directed by, or to have acted or purported to act for or on behalf of, directly or indirectly, the Government of Cuba or any person whose property or interests in property are blocked pursuant to this order; (C) to own or control, directly or indirectly, any person whose property or interests in property are blocked pursuant to this order; (D) to have materially assisted, sponsored, or provided financial, material, or technological support for, or goods or services to or in support of, the Government of Cuba or any person whose property or interests in property are blocked pursuant to this order; (E) to be or have been a leader, official, senior executive officer, or member of the board of directors of the Government of Cuba or an entity whose property or interests in property are blocked pursuant to this order; (F) to be a political subdivision, agency, or instrumentality of the Government of Cuba;

FR Page 25062

(G) to be responsible for or complicit in, or to have directly or indirectly engaged in or attempted to engage in, serious human rights abuse in Cuba; (H) to be responsible for or complicit in, or to have directly or indirectly engaged or attempted to engage in, corruption related to Cuba, including corruption by, on behalf of, or otherwise related to the Government of Cuba, or a current or former official at any level of the Government of Cuba, such as the misappropriation of public assets, expropriation of private assets for personal gain or political purposes, or bribery; or (I) to be an adult family member of a person designated pursuant to this order. (b) The prohibitions in subsection (a) of this section apply except to the extent provided by statutes, or in regulations, orders, directives, or licenses that are issued pursuant to this order, and notwithstanding any contract entered into or any license or permit granted prior to the date of this order; except that this subsection shall not apply to activities authorized by, and shall not affect the validity of, any license issued pursuant to part 515 of chapter 31 of the Code of Federal Regulations. (c) Except to the extent required by section 203(b) of IEEPA ( 50 U.S.C. 1702(b) ), or provided in regulations, orders, directives, or licenses that are issued pursuant to this order, and notwithstanding any contract entered into or any license or permit granted prior to the date of this order: (i) any transaction or dealing by United States persons or within the United States in property or interests in property blocked pursuant to this order is prohibited, including but not limited to the making or receiving of any contribution of funds, goods, or services to or for the benefit of those persons whose property or interests in property are blocked pursuant to this order; (ii) any transaction by any United States person or within the United States that evades or avoids, or has the purpose of evading or avoiding, or attempts to violate, any of the prohibitions set forth in this order is prohibited; and (iii) any conspiracy formed to violate any of the prohibitions set forth in this order is prohibited. (d) I hereby determine that the making of donations of the type specified in section 203(b)(2) of IEEPA ( 50 U.S.C. 1702(b)(2) ) by United States persons to persons determined to be subject to subsection (a) of this section would seriously impair my ability to deal with the national emergency declared in Executive Order 14380 , and I hereby prohibit such donations. (e) For those persons determined to be subject to subsection (a) of this section who might have a constitutional presence in the United States, I find that, because of the ability to transfer funds or assets instantaneously, prior notice to such persons of measures to be taken pursuant to this order would render these measures ineffectual. I therefore determine that, for these measures to be effective in addressing the national emergency declared in Executive Order 14380 , there need be no prior notice of a listing or determination made pursuant to subsection (a) of this section.

Sec. 3 . #sec-3

Travel. (a) I hereby find the unrestricted immigrant and nonimmigrant entry into the United States of aliens determined to meet one or more of the criteria in section 2(a)(i) of this order would be detrimental to the interests of the United States, and I hereby suspend entry into the United States, as immigrants or nonimmigrants, of such persons, except where the Secretary of State, or the Secretary of State's designee, determines that the person's entry is in the national interest of the United States. Such persons shall be treated in the same manner as persons covered by section 1 of Proclamation 8693 of July 24, 2011 (Suspension of Entry of Aliens Subject to United Nations Security Council Travel Bans and International Emergency Economic Powers Act Sanctions).

FR Page 25063

Sec. 4 . #sec-4

Foreign Financial Institutions. (a) The Secretary of the Treasury, in consultation with the Secretary of State, is hereby authorized to impose on a foreign financial institution one or more of the sanctions described in subsection (b) of this section upon determining that the foreign financial institution has conducted or facilitated any significant transaction or transactions for or on behalf of any person whose property or interests in property are blocked pursuant to this order. (b) With respect to any foreign financial institution determined to meet the criteria set forth in subsection (a) of this section, the Secretary of the Treasury, in consultation with the Secretary of State, may: (i) prohibit the opening of, or prohibit or impose strict conditions on the maintenance of, correspondent accounts or payable-through accounts in the United States; and (ii) block all property and interests in property that are in the United States, that hereafter come within the United States, or that are or hereafter come within the possession or control of any United States person of such foreign financial institution, and provide that such property and interests in property may not be transferred, paid, exported, withdrawn, or otherwise dealt in. The prohibitions described in this subsection shall include the making of any contribution or provision of funds, goods, or services by, to, or for the benefit of any person whose property or interests in property are blocked pursuant to this subsection; and the receipt of any contribution or provision of funds, goods, or services from any such person. (c) The sanctions described in subsection (b) of this section apply except to the extent provided by statutes, or in regulations, orders, directives, or licenses that may be issued pursuant to this order, and notwithstanding any contract entered into or any license or permit granted before the date of this order; except that this subsection shall not apply to activities authorized by, and shall not affect the validity of, any license issued pursuant to part 515 of chapter 31 of the Code of Federal Regulations. (d) I hereby determine that the making of donations of the types of articles specified in section 203(b)(2) of IEEPA ( 50 U.S.C. 1702(b)(2) ) by, to, or for the benefit of any person whose property or interests in property are blocked pursuant to subsection (b) of this section would seriously impair my ability to deal with the national emergency declared in Executive Order 14380 , and I hereby prohibit such donations.

Sec. 5 . #sec-5

Delegation. Consistent with applicable law, the Secretary of State and the Secretary of the Treasury are directed and authorized to take all actions necessary to implement and effectuate this order—including through temporary suspension or amendment of regulations or through notices in the Federal Register and by adopting rules, regulations, or guidance—and to employ all powers granted to the President, including by IEEPA, as may be necessary to implement this order. The head of each executive department and agency (agency) is authorized to and shall take all appropriate measures within the agency's authority to implement this order. The head of each agency may, consistent with applicable law, including section 301 of title 3, United States Code , redelegate the authority to take such appropriate measures within the agency.

Sec. 6 . #sec-6

Reporting Directives. The Secretary of the Treasury, in consultation with the Secretary of State, is hereby authorized and directed to submit recurring and final reports to the Congress on the national emergency declared in, and authorities exercised by, Executive Order 14380 , consistent with section 401 of the NEA ( 50 U.S.C. 1641 ) and section 204(c) of IEEPA ( 50 U.S.C. 1703(c) ).

Sec. 7 . #sec-7

Definitions. For the purposes of this order: (a) the term “entity” means a partnership, association, trust, joint venture, corporation, group, subgroup, or other organization;

FR Page 25064

(b) the term “Government of Cuba” means the Government of Cuba, any political subdivision, agency, or instrumentality thereof, including the Central Bank of Cuba, and any person owned, controlled, or acting for or on behalf of, the Government of Cuba; (c) the term “person” means an individual or entity; (d) the term “United States person” means any United States citizen, lawful permanent resident, entity organized under the laws of the United States or any jurisdiction within the United States (including foreign branches of such entities), or any person in the United States; and (e) the term “foreign financial institution” means any foreign entity that is engaged in the business of accepting deposits; making, granting, transferring, holding, or brokering loans or credits; purchasing or selling foreign exchange, securities, futures, or options; or procuring purchasers and sellers thereof, as principal or agent. It includes but is not limited to depository institutions; banks; savings banks; money services businesses; operators of credit card systems; trust companies; insurance companies; securities brokers and dealers; futures and options brokers and dealers; forward contract and foreign exchange merchants; securities and commodities exchanges; clearing corporations; investment companies; employee benefit plans; dealers in precious metals, stones, or jewels; and holding companies, affiliates, or subsidiaries of any of the foregoing. The term does not include the international financial institutions identified in 22 U.S.C. 262r(c)(2) , the International Fund for Agricultural Development, the North American Development Bank, or any other international financial institution so notified by the Office of Foreign Assets Control.

Sec. 8 . #sec-8

General Provisions. (a) Nothing in this order shall be construed to impair or otherwise affect: (i) the authority granted by law to an executive department or agency, or the head thereof; or (ii) the functions of the Director of the Office of Management and Budget relating to budgetary, administrative, or legislative proposals. (b) This order shall be implemented consistent with applicable law and subject to the availability of appropriations.

FR Page 25065

(c) This order is not intended to, and does not, create any right or benefit, substantive or procedural, enforceable at law or in equity by any party against the United States, its departments, agencies, or entities, its officers, employees, or agents, or any other person. (d) The costs for publication of this order shall be borne by the Department of State.

THE WHITE HOUSE, #signature

May 1, 2026.

🏛️Official NARA Filing:FR Doc. 2026-09173 Filed 5-6-26; 11:15 am
Billing Codes: 4710-10-P
📜

Scholarly & Legal Citations

Exec. Order No. 14,404, 91 Fed. Reg. 25,061 (May 1, 2026).