Lesson Plan: To the Shores of Tripoli

A teaching companion to the Time Rhymes story on Jefferson's First Barbary War (1801-1805) and Trump's "Project Freedom" convoy operation in the Strait of Hormuz (May 2026). Designed for upper-secondary or first-year undergraduate use in a course on American diplomatic history, naval history, or international relations.

Learning objectives

By the end of this lesson, students will be able to:

1. Reconstruct the chronology of the First Barbary War from the cut flagpole at Tripoli on 10 May 1801 to the Treaty of Peace and Amity on 4 June 1805.

1. Explain why a great power chooses convoy escort over either tribute or full-scale war, and identify the structural conditions under which each choice succeeds or fails.

1. Compare Jefferson's 1801 squadron deployment, Reagan's 1987 Operation Earnest Will, and Trump's 2026 Project Freedom along three axes: declared purpose, operational design, and downstream consequences.

1. Evaluate the historical record on whether convoy operations alone are capable of resolving structural disputes, or whether they tend to prolong them.

Section 1: Tribute and the structural problem

For a quarter-century before 1801 the four Barbary states (Morocco, Algiers, Tunis, Tripoli) extracted annual payments from European and American merchant powers in exchange for not seizing their commercial shipping. By the late 1790s contemporary estimates put American payments to the Barbary states at somewhere between a tenth and a fifth of all federal revenue. The single payment to Algiers in 1795 alone, around one million dollars, came to roughly a fifth of that year's federal budget.

Discussion:

• What is the structural difference between paying tribute and being defeated in war?

• Why do small powers sometimes succeed in extracting tribute from larger ones?

• What changes when the larger power decides the tribute has become more expensive than the war?

Key concept: A protection payment is a recurring liability. A war is a one-time fixed cost. The breakeven point depends on the discount rate and the expected duration of the relationship.

Section 2: Jefferson's decision, May 1801

On 10 May 1801 Pasha Yusuf Karamanli of Tripoli declared war on the United States by cutting down the flagstaff in front of the US Consulate. His ultimatum, delivered the previous December, had demanded $225,000 per year in tribute, several times the previous annual payment. Jefferson, in office for two months and four days, had refused.

Three weeks after the cut flagpole, before any news of the declaration could possibly have reached him, Jefferson sent Commodore Richard Dale and a squadron of three frigates and one schooner (USS President, USS Philadelphia, USS Essex, USS Enterprise) to the Mediterranean. Their orders: escort American merchantmen, maintain peace with the other three Barbary states, and (if Tripoli proved hostile) blockade Tripoli's harbour.

Discussion:

• Why did Jefferson, who as vice-president had argued for cutting the navy, send a navy squadron in his first months in office?

• Read Jefferson's first annual message to Congress (December 1801) on the Barbary states. How does he frame the decision? What does he ask Congress to authorise that the squadron has not already done?

• Compare Jefferson's 1801 calculation to the Adams administration's continued payments to Algiers and Morocco.

Section 3: The Philadelphia disaster

The USS Philadelphia, under Captain William Bainbridge, ran aground on an uncharted reef just outside Tripoli harbour on 31 October 1803 while chasing a Tripolitan corsair. Bainbridge tried everything to refloat (bow anchors cut away, guns shifted aft, water jettisoned, foremast sawed off), surrendered after Tripolitan gunboats attacked, and his entire 307-man crew was taken to shore, stripped, and imprisoned in a single chamber inside the Pasha's palace for 19 months. Six died.

On 16 February 1804 Lieutenant Stephen Decatur, age 25, sailed the captured Tripolitan ketch USS Intrepid (with 84 hand-picked volunteers concealed below decks, disguised as a Maltese trader) into Tripoli harbour and burned the captured Philadelphia, escaping without American killed. Vice Admiral Horatio Nelson called it "the most bold and daring act of the age."

Discussion:

• The Philadelphia grounding gave the Pasha 307 American hostages and a captured frigate. How did this single accident transform the strategic position of both sides?

• Why was burning the captured Philadelphia worth the risk? Consider both the operational reason (denying Yusuf a refit) and the psychological one.

• Decatur's raid is celebrated as a triumph; Nelson's praise stuck. But it did not end the war, did not free the hostages, and did not change the structural dispute. What is the difference between a tactical triumph and a strategic one?

Section 4: William Eaton and the shores of Tripoli

In November 1804 William Eaton, a former American consul, arrived in Egypt with a different idea. He found the Pasha's exiled older brother Hamet Karamanli hiding from Yusuf's assassins, recruited him, and assembled a force of approximately 400 men: Greek mercenaries, European artillerists, Arab cavalry, 90 men loyal to Hamet, 190 camels and their drivers, and 8 US Marines under First Lieutenant Presley Neville O'Bannon. They marched 521 miles across the Libyan desert in 51 days. On 27 April 1805, supported by a naval bombardment from three of Preble's ships offshore, they took the eastern Tripolitan port of Derna. O'Bannon raised the Stars and Stripes over a captured fortification: the first time the American flag was raised in victory over a fortified position in the Old World, and the first foreign military intervention in U.S. history.

That moment became the line "to the shores of Tripoli" in the United States Marines' Hymn.

Discussion:

• Why did Eaton's plan work where Decatur's raid had not?

• The Marines' Hymn celebrates the shores of Tripoli as a triumph. Did Eaton's victory change the war? Read on.

Section 5: The Treaty of Peace and Amity

While Eaton was still holding Derna against repeated Tripolitan counter-attacks, American consul-general Tobias Lear was negotiating directly with Pasha Yusuf in Tripoli itself. They signed the Treaty of Peace and Amity on 4 June 1805. Terms:

• Yusuf would release the 297 surviving Philadelphia hostages.

• The United States would pay $60,000 in ransom (approximately $1.29 million in today's money).

• The United States would withdraw from Derna.

• The United States would abandon Hamet Karamanli to his fate.

• The United States would no longer pay annual tribute to Tripoli, but would continue paying tribute to Algiers, Tunis, and Morocco for another decade.

The Senate ratified the treaty on 12 April 1806.

Discussion:

• The hostages were freed. Tripoli was no longer being paid tribute. But the United States paid a ransom, abandoned its captured city, abandoned its mercenary ally, and continued paying tribute to three other Barbary states. Is this a victory? On whose terms?

• Eaton was bitter about the abandonment of Hamet for the rest of his life. From his perspective, the United States made a moral compromise to end the war. Was the compromise necessary?

• The wider Barbary tribute problem was finally settled by the Second Barbary War in 1815, ten years later, after Algerian seizures of US merchantmen during the War of 1812. What does this say about whether the First Barbary War actually solved the structural problem?

Section 6: Project Freedom (May 2026)

On Sunday 3 May 2026, after high-level peace talks in Islamabad failed to reach a deal, President Donald Trump announced on Truth Social the launch of "Project Freedom" beginning the morning of Monday 4 May Middle East time. The American military, he said, would escort foreign vessels stranded in the Strait of Hormuz safely out of "these restricted Waterways, so that they can freely and ably get on with their business." He framed the operation as a "humanitarian gesture" and warned that "any interference will be dealt with."

Discussion (the structural mapping):

• Map each element of Project Freedom onto its 1801 counterpart:

• Where do the parallels hold? Where do they break down?

Section 7: Reagan's Operation Earnest Will (1987-88)

The intermediate case is Reagan's Operation Earnest Will (24 July 1987 to 26 September 1988), in which the US Navy reflagged Kuwaiti tankers and escorted them through the same Strait of Hormuz against Iranian attacks during the Iran-Iraq Tanker War. At its peak it involved as many as thirty US Navy ships, including carriers and the battleship Missouri. It was not free of incident: a reflagged tanker hit an Iranian mine on the very first escort mission; the USS Stark was hit by an Iraqi Exocet missile (37 sailors killed); the USS Samuel B. Roberts hit a mine (no killed but the ship nearly broke in two); USS Vincennes shot down Iran Air Flight 655 in July 1988 (290 civilians killed). Iran accepted UN Resolution 598 eighteen days after Iran Air 655.

Discussion:

• Earnest Will succeeded in protecting the convoy, escalated to a wider naval shadow war, and ended with a civilian airliner shot down. Iran went to the table. Was the escort operation the cause, or was the airliner?

• Project Freedom uses the same instrument in the same strait against (this time) a direct Iranian state opponent rather than a state acting through proxies. How does this change the risk profile?

Section 8: The empirical record

In each of the three documented cases of an American convoy operation through a contested strait against a smaller regional power:

| Operation | Years | Outcome | |---|---|---| | Jefferson's First Barbary War | 1801-1805 | 4 years; ransom paid; Derna abandoned; Hamet abandoned; tribute to other Barbary states continued for 10 more years | | Reagan's Earnest Will | 1987-1988 | 14 months; USS Stark + 37 dead; Vincennes + Iran Air 655 + 290 dead; Iran accepted UN ceasefire | | Trump's Project Freedom | 2026- | (in progress as of 4 May 2026) |

Discussion:

• Across the two completed cases, what is the median duration of a US convoy operation against a smaller power blockading a strategic chokepoint?

• What is the median civilian cost?

• What is the median number of stated objectives that are actually achieved by the convoy operation alone, as opposed to by parallel diplomatic or military pressure?

Closing question: If the past is your only guide, what would you predict for Project Freedom?

Suggested further reading

The First Barbary War:

• Ian W. Toll, Six Frigates: The Epic History of the Founding of the U.S. Navy (2006)

• Frederick C. Leiner, The End of Barbary Terror: America's 1815 War Against the Pirates of North Africa (2007)

• Joshua E. London, Victory in Tripoli: How America's War with the Barbary Pirates Established the U.S. Navy and Shaped a Nation (2005)

Operation Earnest Will and the Tanker War:

• David Crist, The Twilight War: The Secret History of America's Thirty-Year Conflict with Iran (2012), chapters on Earnest Will and Praying Mantis

• Bradley Peniston, No Higher Honor: Saving the USS Samuel B. Roberts in the Persian Gulf (2006)

The 2026 Iran war:

• Use the evidence manifest from the Time Rhymes story for primary news sources on Project Freedom and the Islamabad talks.