Whether heroes or opportunists, the O’Brien family of privateers helped America launch its battle for independence.

It was an unlikely setting for one of the American Revolution’s most celebrated naval engagements: a hamlet in a remote stretch of the Maine coast with soils and weather so inhospitable that even today it is lightly settled. What Machias lacked in strategic importance, however, was more than made up for by the bravado of its residents, including the six brothers of the O’Brien clan. They helped spark what some have called the first naval battle of the Revolution, propelled the people of coastal Maine into the conflict, provoked the destruction of one of New England’s key trading cities, and later engaged in Revolutionary privateering.

Although the British dismissed Jeremiah O’Brien and his younger brothers as unscrupulous scoundrels, Americans credit them with mythic accomplishments: the founding of the United States Navy, leading a battle James Fenimore Cooper described as “the Lexington of the Sea,” and having “rendered good service to the cause of freedom” by fighting British-supplied Indians. In fact, we have given their name to a fort; a still-surviving Liberty ship, the SS Jeremiah O’Brien; and five 20th-century U.S. Navy warships—from a World War I torpedo boat to a Spruance-class destroyer that helped sink the Iranian guided-missile frigate Sahand in 1988.

The true story of this maritime band of brothers—long obscured by 19th-century mythmaking—is far more nuanced. Like many privateers in the American Revolution, Jeremiah O’Brien and his brothers mixed heroism with opportunism, tactical brilliance with strategic self-interest. While they fought a rebel cause against an empire, the O’Briens were always more Han Solo than Luke Skywalker, colorful rogues who helped their country by helping themselves.

And in the end, though the O’Briens did not achieve the prominence or respectability of other privateers—the fortunes of the Cabots, Lowells, Peabodys, and other Boston Brahmin families were founded on privateering—they retired in comfort, having served their own interests at least as well as those of their young nation.

In 1775, Machias, the O’Briens’ hometown and base of operations, was a frontier hamlet but 12 years old, the only settlement of consequence for 50 miles in any direction. Unable to coax crops from the glacier-scoured earth, its farmers had turned instead to the forests and foggy, fickle sea to harvest wood and fish for trade with Boston or Halifax merchants. Their dependence on waterborne trade was nearly absolute: Without it, the town would have quickly run out of food and supplies.

The outbreak of hostilities at Lexington and Concord—and the American siege of British forces in Boston—put the people of Machias in a precarious position. Continued trade with Boston or Halifax would supply the British forces that now controlled both ports. Yet without that commerce, they might well starve. Patriots held firm, and soon whole families were subsisting almost solely on clams they dug from the ocean mud. By May, one resident later recalled, the townspeople were already “in a great measure destitute.”

Like many communities in British North America, Machias had divided loyalties. Most residents sided with the patriots, but several loyalist families would flee to British New Brunswick during the war, and the town’s leading citizen was colluding with British military authorities in Boston. It was this man, Ichabod Jones, who would help make the O’Briens famous. Jones, a recent transplant from Boston, owned most of the town’s lumber mills as well as the vessels that carried the lumber to Boston and brought back provisions. Savvy and connected,

Jones served as Machias’s principal lobbyist to the provincial government of Massachusetts, of which Maine was still a part. However, with the advent of hostilities, Jones’s relationship with his neighbors soured. Like many New England merchants, Jones wanted to keep up his trade with British authorities in Boston. When townspeople threatened to intercept and destroy his ships, Jones did what any committed loyalist would do: He turned to the British military for assistance.

In late May, Jones met with British general Thomas Gage, who was mustering British forces and supplies in Boston. Machias, Jones told Gage, could be a vital source of lumber and firewood if the British would give his merchant ships an armed escort. Vice Adm. Samuel Graves agreed, assigning the task to the 50-ton armed schooner Margaretta.

The little convoy caused an uproar when it arrived in the Machias River on June 2. Jones offered supplies to the townspeople in exchange for lumber and firewood for the British in Boston. He called a town meeting for June 6, at which residents would vote on his proposal. Meanwhile, one eyewitness reported, Jones “privately went down” to the Margaretta and persuaded its commander, Midshipman James Moore, to move his tiny warship upriver “so near the town that her guns would reach the houses.” Moore apparently had no intention of making good on his threat: He’d left his four 3-pound cannons stored in the Margaretta’s hold, leaving only 14 light swivel guns at his disposal. “Considering themselves nearly prisoners of war in the hands of a common enemy,” as they were described in a 1775 letter, the residents passed a resolution to accept Jones’s deal.

Having cowed his neighbors into submission, the loyalist merchant then overplayed his hand. When his vessels tied up to the town wharf to distribute supplies, Jones refused to give provisions to townspeople who had voted against his proposal. “This gave such offense to the aggrieved party,” the chairman of the town’s patriots, James Lyons, reported to his Massachusetts counterparts a few days later, “that they determined to take Capt. Jones…and put a final stop to his supplying the King’s troops with anything.” The “aggrieved” included the six sons of 70-year-old Morris O’Brien.

Morris O’Brien had emigrated from Ireland to the colonies while in his early 20s. He had served in Maine native William Pepperell’s 1745 campaign that captured the French fortress at Louisbourg, on the eastern tip of Cape Breton Island, Nova Scotia. In 1764 he moved his family north from southern Maine, where he had established a successful sawmill. In 1775, Morris’s sons—Jeremiah, Gideon, John, William, Dennis, and Joseph—ranged in age from 17 to 31. All were old enough to fight, and all were itching to fight the British.

Calm preceded the storm. Jones, unaware of the plot, spent a few days loading wood into his two large coasting vessels: the 80-ton sloop Unity the 90-ton schooner and Polly. The Margaretta ’s officers also relaxed, going ashore daily, and behaving, wrote one resident, “with civility.” On Sunday, June 11, they attended services at the Machias Congregational Meeting House. They were walking into an ambush.

In secret, Jeremiah O’Brien and Benjamin Foster, a 49-year-old veteran of the French and Indian War, had sent messengers via the winding footpaths to the nearest villages. Dozens of men from these wilderness hamlets responded to the call, muskets and birding pieces in hand, to help defend Machias. On Sunday morning, hidden in the woods on Morris O’Brien’s property, they and their Machias conspirators planned to surround the Meeting House during services that afternoon, and arrest Jones, his nephew Stephen Jones, Midshipman Moore and his officers.

Jeremiah O’Brien initially opposed the plan, saying it would “inevitably bring on the destruction” of Machias because of its dependence on trade. However, Foster would hear none of it, and in the end, all the O’Brien brothers would be at the forefront of the fight.

The ambush did not go as planned. Jones, Moore, and Moore’s officers heard the patriots approach and escaped through the windows of the Meeting House. Jones vanished into the woods, while Moore’s party rushed to the shore and set out in one of the Margaretta’s boats. By the time the O’Briens reached the wharves, Moore had rallied his crew of 20, raised the Margaretta’s flag, and sent a message ashore: His orders were to protect Captain Jones, and “if the people presumed to stop Captain Jones’ vessels, he would burn the town.”

Roughly a hundred patriots promptly set about looting the Unity, which was tied to the wharf, while their colleagues rowed out to the Polly, raised its anchors, and brought it up near the wharf. They had called Moore’s bluff: With only swivel guns on the Margaretta, he could not do much damage to the town. Instead he waited until dusk, quietly weighed his anchors, and drifted downstream to within musket range of the Polly. Racing to beat the British, some insurgents reached the Polly first, cut its anchor line, and drifted it aground. Other townspeople rushed down to the water and, with the help of boats, canoes, and other small craft, lined the shore nearest the Margaretta and made a most audacious demand: “Surrender to America.” Moore, no doubt shocked at their temerity, told them to “fire and be damned”—which they did.

“The firing was smart for a quarter of an hour when Capt Moore cut his [anchor] cables and fell down the river with the tide,” Thomas Flinn, the captain of the lumber schooner Falmouth Packet, would later report. There Moore detained a small sloop, seizing supplies and two of its men before anchoring to await the dawn.

At sunrise the next day, June 12, the O’Brien brothers and 34 others prepared the Unity for combat, building improvised barricades and firing positions from lumber in the hold. These lumbermen, farmers, and fishermen passed around what weapons they had: muskets, swords, hunting rifles, hayforks, and axes. Meanwhile, 20 other men led by Benjamin Foster rowed out to the Falmouth Packet, commandeered it, dumped its uncooperative captain ashore, and started down the river to back up the men on the Unity.

A mile away, aboard the Margaretta, Midshipman Moore observed all this through his spyglass. Seeing he was outmanned, he gave the order to raise anchor and beat a retreat for Boston, two days’ sail to the east. However, as his little warship tacked out of Machias Bay, patriots fired on him from the western bluffs. An extraordinarily lucky shot shattered one of the Margaretta’s gaff spars, the upper poles that held its two large sails in place. Without it, the Margaretta—already “a very dull sailor” according to one Machias resident’s account—lost speed. Limping over to the bay’s eastern shore, the Margaretta headed off an inbound trading sloop and pulled alongside. Moore sent a boarding party scurrying over the bulkheads to seize the sloop’s boom and gaff as well as a pilot to guide them through shoals and islands.

By the time Moore’s men had finished the repair, the Unity and Falmouth Packet were in plain sight astern and rapidly closing. The Margaretta’s boats were cut loose to increase speed, but there would be no escape. Moore ordered the swivel guns loaded and his stock of cast-iron hand grenades filled with powder, fuses at the ready.

Jeremiah O’Brien, in command of the Unity, sought to sail alongside and, when slightly ahead of the Margaretta, turn the Unity directly into its path, hoping to ensnare the vessel. His men were likely to win the boarding action that would follow, especially once Foster’s reinforcements on the Falmouth Packet arrived.

The attack did not go so smoothly. As the Unity approached, the Margaretta’s men hammered it with their swivel guns. The Unity smashed into its adversary from the rear with what must have been wrenching force, its bowsprit ripping the lines supporting the Margaretta’s mainmast and tearing into its mainsail. As Gideon O’Brien—at 29, the second oldest O’Brien brother—led a swarm over the Margaretta’s rail, Moore’s men heaved hand grenades onto the Unity’s deck. Gideon’s men fired at close range, grenades exploding behind them. Blood, screams, and gore erupted all around.

When the smoke cleared, Midshipman Moore was prostrate on the deck with a musket ball in his chest and another in his abdomen. Moved to Jones’s home, he would die the next day. Two men lay dead—a Royal marine and the pilot the British had kidnapped earlier that morning—and five British sailors were wounded. Moore’s youthful first officer was shot and fled to his cabin, effectively ending resistance. Six of O’Brien’s men had been wounded, one of them fatally, but the townspeople had taken on the Royal Navy and won.

By killing the king’s officer and seizing one of his ships, the citizens of Machias put themselves on an irreversible course. From then on the British considered the community a renegade town, subject to brutal reprisal. Securing supplies from Boston or Halifax was now out of the question. Machias, the residents knew, would have to prey on the British to provide for themselves. As one resident would later put it: “War being now commenced, it was considered that it would not do to flinch.”

Machias sent John O’Brien, who was 25 and the third oldest brother, to Massachusetts to seek advice on what to do with the prisoners from the Margaretta. The justice of the peace led a posse to drag Ichabod Jones from the woods, and a local mariner rushed off to the nearest proper town— Annapolis, Nova Scotia—to bring a surgeon to treat the wounded.

Jeremiah O’Brien was appointed commander of the Polly, the most seaworthy of the town’s three-vessel fleet (the Falmouth Packet had been returned to its owner) and set about refitting it as a proper sloop of war. From the Margaretta, they brought over swivel guns and 3-pound cannons; they also erected bulwarks to protect the vessel’s crew and armed themselves with Royal Navy–issued boarding axes, muskets, and cutlasses. They painted a new name on its stern: Machias Liberty.

At the end of June—while the town awaited orders from patriot headquarters outside Boston—Jeremiah sailed the Machias Liberty in pursuit of another Royal Navy schooner, HMS Diligent, a 100-ton, 8-gun vessel rumored to be cruising the mouth of the Bay of Fundy to the east. For two weeks, they patrolled the unforgiving Maine coast and the foggy approaches to the Bay of Fundy. There was no sign of the Diligent or cattle vessels said to be en route from Windsor, Nova Scotia, to Boston.

On their return to Machias on July 15, Jeremiah and his crew learned that the Diligent and the 15-ton armed cutter Tatamagouche, having heard of the attack on the Margaretta, had arrived that same day in Bucks Harbor, just two miles to the south. Before Jeremiah could set sail against the British, Stephen Smith, a local patriot, arrived in town with a prisoner: the Diligent’s captain, James Knight. On the Diligent’s arrival, Smith and several other men had hidden on an island at the mouth of Bucks Harbor. When Knight rowed ashore, Smith’s party intercepted him.

O’Brien—backed up by Benjamin Foster in a stolen merchant sloop—sailed to Bucks Harbor. Without their captain, the British surrendered without firing a shot. Suddenly Machias was home to 100 prisoners and the largest rebel naval force in the Americas. Its people had earned the respect of revolutionaries and the everlasting ire of British military authorities, who feared an invasion of loyalist Nova Scotia. When O’Brien’s vessel was seen outside the British naval anchorage at Windsor, the colony’s governor, Francis Legge, warned General Gage that “the pirates of Machias” could easily scale the facility.

Certainly naval officers in Nova Scotia took the threat from Machias seriously. When Legge asked Capt. Edward Meadows, commander of British naval forces in the province, to send the 14-gun Senegal to destroy the “pirates” at Machias, the officer said the warship would not be equal to the task. Persuaded, Legge dispatched the entire squadron, and was forced to send detachments of soldiers to defend the dockyards of Windsor and Halifax while the naval vessels were away. Without reinforcements, Legge warned General Gage, there would be little hope of sending more supplies to Boston.

In Boston, meanwhile, Vice Admiral Graves was furious, and not only because rebels had taken three of his vessels. Midshipman Moore, who had died in agony in Machias, was a cousin from his mother’s side of the family. The residents of Machias, Graves vowed, would pay a terrible price.

As Graves stewed—and Captain Meadows dithered with his squadron in the Bay of Fundy—Jeremiah O’Brien lobbied for arms and material. From the provincial legislature in Watertown, Massachusetts, he secured commissions making the Machias Liberty and Diligent part of the new Massachusetts Navy. While Gen. George Washington’s ragtag army was engaged in a difficult siege of occupied Boston, provincial authorities gave O’Brien £260 to secure supplies and ready his vessels.

Colonials in New England celebrated the Machias exploits. The Massachusetts legislature passed a resolution thanking O’Brien and Foster. John Adams included O’Brien on a list of just 22 people “suitable for naval commands” in the soon-to-be-formed Continental Navy. Under his command, the people of Machias took to calling themselves “the dread of Halifax and the British Navy.”

Even so, less than flattering reports were already circulating about O’Brien. On August 16, 1775, while directing the Boston siege from Cambridge, General Washington took the time to write to a leading Massachusetts official that O’Brien had violated procedure by seizing the personal possessions of the naval officers captured or killed at Machias. Unless the Machias men returned the officers’ belongings, Washington noted, the seizure would “much dishonor the American arms.” More dishonor and disagreeable consequences were soon to come.

Technically Jeremiah was now an officer in the Massachusetts Navy, commander of a four-vessel squadron consisting of the Machias Liberty, Diligent, Margaretta, and Tatamagouche. He and his men—including brothers William, the 22-year-old mate aboard Machias Liberty, and John, mate of the Diligent— received their pay from the public treasury and were supposed to follow the orders and regulations of the Massachusetts legislature. But Jeremiah proved better at collecting salaries than following orders and procedures.

Indeed, though ordered to cruise against enemy shipping, Jeremiah seems to have barely left port in the first months of his command. There are no reports that he captured any vessels from September 1775 to March 1776, when he finally sailed up the Bay of Fundy after months on the public payroll.

By contrast, in the few weeks he was away lobbying legislators, another captain had used the Machias Liberty to launch a daring raid on Saint John, New Brunswick, sacking the king’s fort and capturing several redcoats and a merchant ship laden with cattle, sheep, hogs, salmon, and butter. However, with Jeremiah O’Brien back in charge, the “flying squadron” appears to have remained comfortably in harbor.

As O’Brien sat in port, the people of Falmouth (modern Portland, Maine) paid the price for his earlier actions. In early October, Admiral Graves ordered Lt. Henry Mowat of the 180-ton, 8-gun sloop of war Canceaux to crush the rebellious ports of northern New England, “particularly Machias where Margaretta was taken.” But Lieutenant Mowat encountered unfavorable winds en route to Machias and decided instead to punish Falmouth, bombarding the town for nine hours and setting fires that consumed three-quarters of the city’s buildings. The unprovoked carnage shocked the public on both sides of the Atlantic. [See “Burning Falmouth,” MHQ, Autumn 2009.]

Infuriated mariners asked for licenses to arm their vessels and attack British shipping as so-called privateers. The role of these vessels—which outnumbered the Continental Navy by 200 to 1—in the success of the American Revolution is difficult to overstate. Together they captured some 2,200 British vessels, including warships and troop transports, paralyzing commerce across the empire. The Irish linen fleet felt the need to travel in convoy for the first time in history.

British newspapers from the period had nothing but scorn for the Continental Army, characterizing its soldiers as incompetent cowards, but the privateers engendered fear and respect, particularly after a series of bold attacks on Great Britain itself, most famously by John Paul Jones. As O’Brien would do, many privateering captains shifted back and forth from military to private command, including such naval heroes as Jones, Silas Talbot (sometime commander of “Old Ironsides,” the USS Constitution), and Stephen Decatur.

Not surprisingly, the Continental Navy often functioned as an auxiliary to the privateering fleets and adopted many of their tactics, ship designs, and organizational culture. During the critical early years of the Revolution—with the British blockading the ports—the privateers provided many of the weapons and much of the material that kept Washington’s army in the field.

But the spectacular success of the Colonial mariners against British shipping was undermined by Jeremiah O’Brien’s growing reputation for inaction. In July 1776, a group of leading citizens led by Maj. Gen. Benjamin Lincoln, commander of American troops in newly liberated Boston, called on the Massachusetts legislature to investigate Jeremiah. Lincoln and his colleagues said he boasted of ignoring orders and alleged that he had “offered one, if not both, of [his] vessels for sale.” O’Brien’s ships, they added, “have cost the public large money, but have effected very little.”

Similarly John Adams received a letter from his wife’s uncle, Isaac Smith, complaining that the people were “paying for a vessel to guard the Eastward Coast [that] has been lying in harbor the chief of his time and doing no service—O’Brien!” Meanwhile, the owners of the few vessels Jeremiah had captured since joining the Massachusetts Navy filed suit against him in Boston, claiming the captures were unlawful. The court saw merit in the case, ordering the state to freeze O’Brien’s wages until the matter was resolved.

Machias residents raised doubts about O’Brien too. In late August 1776, Benjamin Foster and his colleagues on the local Revolutionary committee wrote the Massachusetts legislature charging that O’Brien had embezzled public funds by collecting the salaries of sailors who had never served on his vessels. At the same time, local militia officer Francis Shaw discovered that valuables were missing from the Diligent. Shaw relieved O’Brien of command of the ship and sent it back to Boston. O’Brien’s tenure as a naval officer was ending.

Jeremiah O’Brien did his best to defend himself. In October he petitioned the state government, “praying that he may be granted a supply of money and provisions” while claiming that he had advanced $500 to $600 to his men since salary payments had been suspended in August. He got his allies in Machias to write too, contending that “unjustifiable methods had been taken to injure the character of Captain Jeremiah O’Brien.”

In the end the government’s decision was succinct and severe. On October 15, 1776, the legislature directed the sheriff to seize all cannons and stores from the Machias Liberty and discharge the vessel, its commander, officers, and men from state service. It ordered both the Machias Liberty and the Diligent hauled up, and fined O’Brien £46 for embezzlement, or improperly seizing goods. As Boston’s John Bradford, who was Continental marine agent for all navy ships, later wrote John Hancock, the leaders of Massachusetts “are glad they’ve got rid of him.”

Dismissed from the state navy, the O’Brien brothers were out of work. But three of them—Jeremiah, John, and William—continued to sail as privateers. Gideon and Dennis, the second youngest, gave up life at sea and returned home to Machias. The youngest brother, Joseph, followed them ashore but continued to invest in his older brothers’ schemes.

In August 1778 Jeremiah secured a privateering commission for the sloop Resolution, carrying 10 swivel cannons and 25 men, including William. The vessel appears to have made only one extended cruise, capturing a ship in the Gulf of Maine loaded with pork. By odd coincidence, that ship had been captured days earlier by Henry Mowat, the naval officer who had razed Portland; it was commanded by Mowat’s mate, who now found himself a prisoner of the O’Briens. Jeremiah probably sold his prize and its cargo and returned to Machias to live from the proceeds; his name does not appear again in documents connected with privateering or maritime warfare until late 1780.

John’s return to privateering was a bit delayed. After his release from the Massachusetts Navy, he appears to have joined the Continental Navy. In May 1777, a person by his name appeared in a list of men who had signed up for Washington’s army, collected the bounty of £26, but then run off to the navy. In March 1779, his name surfaces again among American prisoners captured by the British and interned in a Barbados jail.

In early 1779, perhaps after having been released from prison, John appeared in Newburyport, Massachusetts, where he hired out as a privateering captain, first on the 120-ton brig Adventure and then, a few months later, on the 6-gun, 70-ton schooner Hibernia, where William O’Brien joined him as mate. Over the year, John and William captured at least six vessels; their take must have been considerable, since John stayed ashore for the next nine months while his own privateer was built. The Hannibal, awarded its commission in late April 1780, was a 250- ton, 26-gun vessel with a crew of up to 130. It was a frigate-sized ship that could easily overwhelm most merchantmen. On their first cruise, John and William took their vessel to the Caribbean, where they allegedly captured “several important prizes.”

The two brothers appeared to be on the path to merchant princedom, peers to Boston Brahmins who were using privateering gains to move into the vacuum left when Boston’s loyalist merchants fled the country. However, late in the summer of 1780, John O’Brien made an ill-fated decision: He offered his brother Jeremiah command of the Hannibal.

Commanding a far more powerful vessel than he was accustomed to sailing, Jeremiah decided on a high-risk, high-reward strategy. In October he sailed to the approaches of British-controlled New York Harbor, where the Royal Navy’s transatlantic convoys assembled. There he hoped to sack merchant vessels while dodging the frigates assigned to protect them. Instead Jeremiah quickly found himself in flight from two heavily armed frigates. Whereas he might have been able to outmaneuver them in a sloop or schooner, his new ship was square-rigged and no more nimble when sailing into the wind than its pursuers. After a 48-hour chase, the larger frigates overtook the Hannibal, forcing Jeremiah to surrender.

The British transferred O’Brien and his men to the infamous Jersey, one of four decommissioned naval vessels moored in Brooklyn’s Wallabout Bay to house rebel prisoners. Survival on the Jersey was extremely uncertain. A former 64-gun ship of the line, it was now rotting and vermin infested, its masts and rudder gone and its gun ports sealed up, restricting ventilation to the thousand prisoners locked in the hold. One prisoner recalled that when first brought aboard the Jersey, the stench from one of the tiny ports produced on deck “a sensation of nausea far beyond my powers of description.” Americans dying of smallpox, dysentery, and yellow fever were crammed in with the uninfected. Jailers cooked what little food was allotted to the inmates in corroded copper vats, exposing the prisoners to slow poisoning. The ship earned its moniker, “Hell Afloat.” An estimated 7,000 prisoners died on board during the war.

It appears Jeremiah O’Brien spent as long as six months on the British released the rest of his crew but singled out O’Brien for detention in England. He seems to have been transferred across the Atlantic in January 1781 in the Jersey, and then, during a prisoner exchange, the company of at least one of his officers, marine captain Nathaniel Nazro, who described the ocean passage as “long and tedious,” with several men dying on the way “through cruel treatment.” In England the British took O’Brien and Nazro to the notorious Old Mill Prison in Plymouth.

A walled compound set on a windswept bluff, the prison held between 800 and 1,000 men whom the British gave so little food that they ate grass, snails, and rats to stave off hunger. Escape attempts were common. One privateer inmate got away by digging under the wall. Others bribed guards or found ways to scale the defenses. Those caught, including Nazro, spent 40 days in the “black hole,” a dungeon where they were put on half rations.

O’Brien, after some nine months at Old Mill, engineered a particularly ingenious jailbreak, here described by his brother John: “He purposely neglected his dress and whole personal appearance for a month. The afternoon before making his escape, he shaved and dressed in decent clothes, to alter very much his personal appearance, and walked out with the other prisoners in the jail yard. Having secreted himself under a platform in the yard, and thus escaping the notice of the keepers at the evening round-up, he was left out of the cells after they were locked up for the night. He escaped from the yard by passing through the principal keepers’ house in the dusk of the evening. Although he made a little stay in the barroom of the house, he was not detected, being taken for a British soldier.”

Hidden with another escapee by sympathizers, Jeremiah eventually rowed across the English Channel to safety in France, where Ambassador Benjamin Franklin helped former POWs return to the colonies. Jeremiah arrived back in Machias by December 1781, and, unbowed, took up command of another privateering schooner.

Having lost their own ship, both Jeremiah and John O’Brien spent the rest of the war as privateering captains, raiding British shipping for a share of the plunder. Details are sketchy, but they appear to have been modestly successful, their services sought by the owners of at least four private warships during the final years of the war.

With peace, both men returned to Machias, where Jeremiah would eventually be appointed to the lucrative position of collector of customs. William, who had joined the merchant marine, died of fever in Bilbao, Spain, in 1787, while Gideon and Joseph made new homes in Pennsylvania. Their father, Morris, survived the war and died in 1799.

All the brothers were too old to take part in the War of 1812, but Jeremiah got his last licks at the British anyway. When British forces occupied eastern Maine in the fall of 1814, soldiers searched his Machias home for arms and ammunition. Finding nothing, the British officer suggested he and O’Brien have a toast. Jeremiah allegedly jumped to his feet with a mug of cider to exclaim, “Here’s to the success of the American arms!” The officers stood for a moment in stunned silence before breaking into laughter.

Jeremiah died of natural causes in 1818, his brother John in 1832. The O’Briens’ exploits were celebrated in the new United States beginning in the early 19th century, when the first detailed histories of the young republic’s towns and states were recorded. Seeking to honor heroes, these accounts skipped lightly over Jeremiah O’Brien’s dismissal from the navy and embellished his deeds.

Midshipman Moore, some mythmaking historians posited, attacked the town because of a newly erected liberty pole; one account had him escaping capture in the church because of the stupidity of the only black resident of Machias.

Others invented dramatic dialogue, including heated exchanges between Moore and the O’Briens, and an inventive, operatic story held that Moore, stopping by Machias on his way to be wed, had his bride aboard the Margaretta. “When the dying lover was brought to [her],” Machias historian George Drisko proclaimed in 1904, “the shock was too great…and she passed on in less than a year.” By that time, Maine historian Edwin Churchill has pointed out, the Margaretta incident was “heavily encrusted with local traditions and patriotic folklore.”

The first U.S. Navy vessel to bear the O’Brien name was christened in 1900, when the mythic tales were uncontroverted. That vessel—Torpedo Boat 30, the USS O’Brien—was sponsored by Mira O’Brien, Joseph’s great-great-granddaughter. On the eve of World War I, Marcia Bradbury Campbell sponsored construction of destroyer DD-51, then christened it after her greatgreat-granduncle, Jeremiah O’Brien, a man once denied naval command. Gideon O’Brien’s great-great-great-granddaughter, Josephine O’Brien Campbell, was on hand in 1940 to christen DD-415 with the O’Brien name, and again in 1944 for the launch of DD-725. (At the 1940 launch, her father displayed a cutlass said to have been captured from the British by Gideon, while members of the Jeremiah O’Brien Association looked on.)

A final USS O’Brien, DD-975, was launched in 1976 and decommissioned in 2004. One of only two surviving World War II Liberty ships is the SS Jeremiah O’Brien. Once it took part in the D-Day invasion of Normandy; now it is moored at Pier 45 in San Francisco.

Naval role models the O’Briens were not. Nevertheless, Jeremiah O’Brien and his brothers were examples of a different sort of Revolutionary figure often lost in history: freelance rogues, acting bravely when profit and patriotism coincided but avoiding the field when they did not.


Originally published in the Summer 2010 issue of Military History Quarterly. To subscribe, click here