Jeremiah O’Brien was born in 1744 in Kittery, in the district of Massachusetts that would later form the state of Maine, the eldest of six sons of Morris and Mary O’Brien—Irish Catholic immigrants from County Cork. In 1765, the family moved to Machias, a frontier settlement on the Maine coast. There, the O’Briens established a sawmill operation along the Machias River. There, the family prospered, and by the time he was an adult, Jeremiah had become prosperous through the lumber trade, which also entailed operating coastal sloops that shipped timber to other New England ports.

O’Brien was also a committed patriot, devoted to the land that had afforded his family prosperity they could have never known in British-ruled Ireland. O’Brien was a Machias Committee of Safety member, the local governing board. On receiving reports of the battles of Lexington and Concord, O’Brien, and others rallied the citizens to the cause of America’s liberty. As a tangible sign of their commitment, they erected a “Liberty Pole” of a tall pine tree stripped of branches except for the top. Before it, they solemnly pledged to resist British oppression even if it required the sacrifice of their property and blood in defense of the town.

That vow was soon put to the test.

On June 7, 1775, the British armed schooner Margaretta arrived, escorting two merchant sloops, the Unity and the Polly, which carried provisions and were intended to be loaded with lumber for British forces. The townspeople of Machias correctly deduced that the lumber was to be used to build British fortifications in Boston. The captain of the merchant ships informed the townspeople of Machias that he would only unload supplies much needed by the town if the lumber were loaded. In an already tense situation, the acting “Captain” of the Margaretta, in fact a midshipman named James Moore, perhaps flush with his new authority, demanded that the Liberty Pole be taken down. John O’Brien, a younger brother of Jeremiah, is said to have replied, “Must come down? Those words are very easily spoken. You will find, I apprehend, that it is easier to make than it will be to enforce a demand of this kind.” The astonished Moore replied, “. . . my orders are pre-emptory and must be obeyed. That liberty pole must come down, or it will be my painful duty to fire upon the town.”

Such a threat pushed even the town’s most conservative members to rebellion.   Jones and Margaretta‘s officers barely escaped an attempt to capture them while ashore attending church services. Jones and his men ran to the Margaretta and hastily slipped away while firing a few warning shots in the process. After anchoring downriver, Moore, having learned nothing from his prior threats, sent back word to Machias that if harm came to the merchant captain or his sloops, the Margaretta would return to burn the village.

On June 11, Jeremiah O’Brien and his brother Daniel captured one of the provision ships. Unity. With a rough collection of armaments, muskets, fowling pieces, a small cannon, pitchforks, axes, and a party of 35 volunteers, of which five were his brothers, O’Brien set out aboard the Unity to pursue the Margaretta.   Witnessing the action with his spyglass, Capt. Moore decided to make a run for the open ocean.

The Unity caught up with the Margaretta at sea on June 12, 1775. Once within hailing distance, Moore demanded that O’Brien keep off and threatened to fire. O’Brien replied, “In America’s name, I demand you surrender!” Despite the superior firepower of the British ship, O’Brien was able to come alongside the British vessel and board. 

Recognizing that Jeremiah O’Brien was the heart and soul of the attack, Moore directed his men to fire at the audacious captain. O’Brien remained unscathed, but Captain Moore was felled by a shot from a Yankee marksman who had witnessed the attempt on O’Brien’s life.

O’Brien personally hauled down the British ensign. It was the first naval victory of the American Revolution. The Unity was transformed into an armed cruiser with the weapons captured by Margaretta. O’Brien rechristened her the  Machias Liberty, and she was employed as the first American armed cruiser of the Revolution.

When news reached them of O’Brien’s actions, the British sent the ships HMS Diligent and HMS Tapnaquish “. . . to bring the obstreperous Irish Yankee in for trial.” Jeremiah O’Brien and the Machias Liberty captured them both.

O’Brien continued to serve as both a naval commander and privateer. Over the course of the war, he commanded at least six vessels, including the Resolution, Cyrus, Tiger, Saint Vincent, Little Vincent, and Hannibal. Operating in New England and Nova Scotia waters, O’Brien’s crews captured multiple British supply ships, disrupting British operations in the North Atlantic.

In 1780, while commanding the Hannibal, O’Brien was captured and imprisoned first aboard the notorious  Jersey prison ship in New York Harbor, then transferred to Mill Prison in Plymouth, England. He was held there for nine months. O’Brien arranged for the prison’s washwoman to smuggle in fresh civilian clothing. In exchange, he gave her his last guinea. After weeks of intentionally letting his appearance degrade to where the guards would not be likely to remember his original appearance, he cleaned up, changed into the fresh civilian disguise, and exited the prison during the evening guard change. He even dared to enter the local tavern for some refreshment before making his way to the coast, was ferried across the Channel to France, and returned to America by the end of 1781.

After the war, O’Brien was appointed customs collector in Machias, a position he held until he died in 1818. He is buried in the O’Brien family plot in Machias, Maine.

Five U.S. Navy ships have borne his name. The SS Jeremiah O’Brien, a World War II Liberty Ship, is preserved in San Francisco and remains one of the last operational vessels of its kind.

As the United States approaches its 250th anniversary, the story of Captain Jeremiah O’Brien deserves renewed attention. He secured the first American naval victory of the Revolution, led multiple privateering missions, and served his country long after the fighting ended. He did all this as a son of Irish immigrants in a time when that alone could be a barrier. O’Brien’s name deserves to be better remembered—not out of sentiment but because he earned it.