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Military outsourcing is making headlines, but it didn’t begin in Iraq. Private contractors played a key role in winning American independence.

A frenzied shootout in a Baghdad intersection last September reportedly left 17 civilian bystanders dead. The shooters, providing security for a convoy of officials, turned out to be neither U.S. nor Iraqi military, insurgents or terrorists. They were employees of the North Carolina–based security firm, Blackwater Worldwide, and with this high-profile incident the matter of private contractors operating in Iraq began to come under intense scrutiny. Many Americans were surprised to learn that there are more U.S. civilians in Iraq than uniformed personnel, a large number of whom provide armed protection for reconstruction projects and visiting dignitaries. Suggestions arose that they are “hired guns” operating outside the rules of conventional warfare. “It’s a very dangerous precedent for our country,” said one U.S. senator about the government’s deployment of private contractors, “and one that we’ve never been in before.”

In fact, America was in a similar situation during the Revolution, when a cash-strapped Congress, unable to launch an effective navy of its own, licensed approximately 1,700 privately owned warships to roam the ocean in quest of British prizes. Essentially legalized pirates, these Revolutionary privateers carried congressional commissions that forbade attacks on neutral shipping and the mistreatment of captives but otherwise gave them free reign to rob and plunder. Men who became privateers were driven as much by greed as by patriotism and, similar to today’s contractor controversy, they generated anger and resentment among those serving in the Continental ranks. Privateers also gained a reputation for barbarism in combat that infuriated the British and embarrassed many Americans.

George Washington initiated the enterprise off-handedly during his army’s protracted siege of British-occupied Boston in the fall of 1775. “Finding we were not likely to do much in the land way, I fitted out several privateers, or rather armed vessels, in behalf of the Continent.” With an offer of a percentage of spoils as inducement, his call for citizen sailors to hijack inbound supply ships tapped the same vein of self-interest and comradeship that had led the colonies to seek independence in the first place. The result was a private seaborne insurgency whose ever-widening ravages on enemy commerce ultimately proved instrumental in turning British popular opinion against the war.

While Washington went about outfitting a flotilla of lightly armed schooners, debate commenced in Congress about whether to finance a full-fledged American battle fleet. Though many members thought the idea of taking on the Royal Navy insane, in October 1775 Congress established the Marine Committee to oversee the production of 13 frigates.

Meanwhile Massachusetts, with its deep-rooted culture of fishing, shipbuilding and ocean trade, considered whether to unleash its citizens’ “pecuniary zeal” by allowing state-sponsored privateering. In a tradition dating back centuries, governments at war had authority under international law to license independent operators to snatch the merchant cargoes of a declared foe. There had already been incidents off the Massachusetts coast of British supply crews abandoning ship down one side as local marauders clambered up the other side wielding clubs and cutlasses; the loot from these raids had whetted popular visions of bigger gains to come. To legalize privateering therefore promised an instant navy at no cost to the colony.

Two points argued against it, however. If the privateering activity flourished, fewer mariners would sign up for government service. And it had the potential to encourage social mayhem. “No kind of business,” one lawmaker complained, “can so effectually tend to the destruction of the morals of people.”

Supporters sneered. In the face of British tyranny, they said, “The delicacy is absurd surely.”

Massachusetts officially endorsed privateers in November 1775 with “An Act For Encouraging the Fixing out of Armed Vessels.” Termed “a political curiosity” when it was reprinted in London soon thereafter, the act permitted people to “equip any vessel to sail on the seas, attack, take and bring into any port in this colony all vessels offending or employed by the enemy.” It outlined procedures for obtaining commissions and laid the groundwork for establishing “prize courts” to assess and apportion the booty.

British leaders shrugged off the strategic implications. “Those vermin” would be easily crushed, they said, “especially when their loose discipline is considered.” But an unsigned letter from a British naval officer stationed in Boston and published that winter in a London newspaper gave a darker assessment. “They are bold enough to dare and do anything,” he wrote of the American sea raiders. “Whatever other vices they may have, cowardice is not one of them.”

In March 1776, Congress followed suit with a proclamation targeting “all vessels” belonging to Britain as fair game for civilian warships. After months of “vitriolic” debate “on the general theme of business and patriotism,” leaders in Philadelphia embraced the enterprise in a big way, going so far as to distribute preprinted, preauthorized commission forms complete with blank spaces where names of ships, captains and owners could be inserted with minimal fuss. John Adams, an early supporter of privateering, exalted, “It was always a measure that my heart was much engaged in.”

To receive a congressional commission, a privateer posted a bond of up to 5,000 pounds as an assurance that captives would not be mistreated and that the privateer would not knowingly raid American shipping or that of neutral governments. In return, 100 percent of any prize captured went to the privateer ship. Typically, the owners and investors got half the money from the sale of the prize; the other half was divided among the crew. Agents who brokered the sale also took a small commission.

In the first months immediately following the official authorization by Congress of privateers, dozens launched from Massachusetts, New Hampshire and especially Rhode Island, whose reputation for “contraband, quirkiness, and eccentricity” was exemplified by the trading firm run by John and Nicholas Brown. The company dealt in pig iron, African slaves, molasses imports (for distilling rum) and the running of foreign-bought gunpowder through the Royal Navy’s offshore blockade. Privateering was a natural fit, and the brothers immediately set about cutting gun ports through their trade vessels’ bulwarks and clearing holds to make room for the extra crewmen needed to sail captured prizes home for auction. They also were named to lead the congressionally appointed Rhode Island Frigate Committee, which oversaw the construction of Congress’ frigates at Providence.

Weapons shortages slowed the rush to get into the game, but the Browns solved the problem by converting their iron foundry to a cannon factory. Accused of charging “extortioners” prices for the guns for Congress’ frigates, they gave preference to their own vessels and advertised for crews with promises of quick fortunes, congenial captains, ample alcohol and a thrilling opportunity to smite “the tyrant’s pilferers.” In October 1776, the Frigate Committee, then chaired by John Brown, absolved the brothers of charges of war profiteering.

Pronouncements made against Blackwater (“It’s maddening to see contractors act as if they’re above the law,” said one congressman) echo similar outcries against the Browns and other privateering entrepreneurs in 1776. But the fact remained that while Congress struggled to outfit a handful of warships, Rhode Island businessmen launched 65 armed vessels between April and November of that year, returning 41 enemy prizes to Providence (and many others to ports elsewhere) with a value equivalent to about $100 million today. So when John Brown defended his wartime gains by asserting that he was “as deeply engaged in the cause of the United States as any other men on the continent,” he had a fair point.

Beyond their business motives, security contractors in Iraq have been accused of soliciting America’s uniformed soldiers to leave the service for the higher paying private sector. “Contractors are looting our military,” wrote one New York newspaper columnist, “while wrapping themselves in the flag.”

The outburst could easily have come from John Paul Jones, who was stationed in Providence just as the explosion of privateering started luring Continental sailors to jump ship to civilian vessels. Local ship owners, Jones raged, “wink at, encourage, and employ deserters from the navy. What punishment is equal to such baseness? And yet these men pretend to love their country!”

In 1777 the young captain would skipper the 18-gun sloop, Ranger, across the Atlantic with a vow “to draw off the enemy’s attention by attacking their defenseless places,” a plan fulfilled the following spring in his daring hit-and-run raid on the British port of Whitehaven. However, as to his prediction that he “would do infinite damage to their shipping,” it was actually the swarms of privateers he so loathed who came closer to achieving that goal. Indeed, while still skeptical of America’s ability to defeat them on the battlefield, the British were forced to concede one point about rebel privateers that diplomats on the European continent had noted in July 1776: “What is certain on the side of the Americans is their activity at sea and the ships of the crown they are capturing.”

The loss of the American commercial market had been devastating for Britain’s economy. The pain was compounded by the harassment of British merchant shipping. The degree to which the ocean soon teemed with vessels at cross-purposes of trade and predation is evident in a report from a British skipper sailing in convoy across the Atlantic. Sighting more than 150 ships along the way, he found the sea “alive with privateers” trying to pick off straggling transports like wolves circling an animal herd. “One son of a bitch ran amongst us but was too small to attack our convoy.”

In the West Indies alone, whose position as the hub of Britain’s New World trade made it the primary hunting ground for at least a hundred New England privateers by May 1776, maritime losses reached 2 million pounds within a year of Congress’ authorization of private warships. Royal Navy officers “on cruising station” in the West Indies realized, as their superiors in London as yet did not, that it would only get worse. “Time is drawing fast,” one wrote a colleague, “that requires our presence in the English Channel.”

Up until then, most American vessels that crossed the ocean were transports bearing commodities such as tobacco and lumber to exchange for European munitions. The privateers among them were adventurous predators who might provision in French and Spanish ports but rarely sold prizes there (doing so violated those nations’ neutrality agreements with Britain), dispatching them instead back to America for appraisal and auction.

The first warship to base its operations in Europe was the 16-gun Continental brig Reprisal. Under its captain, Lambert Wickes, Reprisal took Benjamin Franklin to France in December 1776 to direct Congress’ effort to forge an alliance. Reprisal went on to prowl the British coastline, capturing 13 merchant vessels and sinking three before being chased into a French harbor by an enemy frigate.

Small ships like Reprisal and most privateers had little choice but to flee before a frigate’s firepower, which could bring a barrage of hurtling metal from up to two dozen 12-pound cannons mounted along each side. The frigate HMS Brune, for instance, once obliterated Volunteer, a 12-gun schooner out of South Carolina, with a single broadside. In trying to treat the many wounded among Volunteer’s 61 crewmen, the British boarding party found the vessel “so much damaged that we hardly had time to get them all on board before she sunk.” Similarly, a Boston privateer, Speedwell, carrying 14 guns and 90 men, took a frigate’s broadside “between wind and water” (the portion of the hull normally below the waterline but exposed to the air if the vessel is heeled over in the wind). The result was that “she immediately foundered, and all her crew perished in the accident.”

In May 1777, another American skipper, Gustavus Conyngham, sailed aboard Surprise with 25 men from the French port of Dunkirk and snagged Prince of Orange, a mail boat plying between Holland and the British port of Harwich. London’s Public Advertiser raged: “The capture of the Orange is a complete refutation of what we have been so often told of the reduced state of the Americans. They have hitherto kept us in sufficient play on their own coasts, and now, in their turn, they even venture to assail ours.”

Panicky rumors flew in Britain of “no less than thirty” privateers fitting out in France with international crews said to include “a number of our best seamen, allured by the prospect of getting a great deal of prize money.” Insurance rates on shipments across the Channel skyrocketed as unverified sightings of privateers “infesting” waters from Ireland to Spain poured in. Newspapers mocked “the clerks of the Admiralty” for their rosy war reports and started highlighting demeaning incidents such as military transports surrendering to privateers armed with wooden guns “for deception” and a Royal Navy frigate accidentally discharging a celebratory holiday volley into an adjacent troop ship.

Conyngham, whose commission was an ambiguous document naming him a Continental officer with a privateer’s rights to captured booty, continued his attacks with another Dunkirk-based vessel, Revenge, seizing 14 prizes and sinking two dozen others “by his bold expeditions,” winning notoriety in the London press as “the Dunkirk pirate.”

British political and military leaders decried the hit-and-run combat style of Revenge and the many other warships now swarming European waters. For the hawks in Parliament, a perception of the privateers as “bragging, cowardly banditti” was reason enough to step up efforts to destroy them. One report of the capture of a supply ship alleged that “rebels stripped the killed and wounded, robbed every article of clothes, bedding, and provisions belonging to the sick, burned the cutter and added every insult to the distress.” And any foe that would, “against the laws of God and Man,” fire on a vessel under a flag of truce deserved, it was declared in Parliament after one such incident, “all the horrors of rebellion,” by which was meant no mercy.

Disgust with the “unequal terms” on which Britain engaged the privateers was expressed by one of the Royal Navy’s ablest captains, Andrew Snape Hamond of the 44-gun HMS Roebuck. Hamond complained of “treating them with openness and generosity while they are daily practicing every kind of art, treachery and cruelty to destroy us.” He particularly deplored the privateer trick of rigging abandoned vessels with combustibles that caused powder magazines to explode after British seamen took possession, a scene “horrible to behold,” one witness wrote. “It went off like the sound of a gun, blew the boat into pieces and set her into flame.” Another such incident left onlookers horrified as the explosion sent “thirty to forty” Redcoats into the air. “The water was covered with heads, legs, arms, and entrails.”

Allegations of atrocities committed by an adversary are common in war, of course, and underscore history’s dictum that the truth is colored by perception. What for the privateers was a necessary guerrilla-style of naval battle was, in the British view, “an unmanly way of fighting.” In broad terms, that same sort of subjectivity doubtless plays a part in the current criticism of military contractors in Iraq. For those who see America’s incursion there as irrevocably misguided and ill-conducted, the contractors are bound, as the contemporary military historian Robert D. Kaplan observed, to “appear to constitute a rogue, mercenary element favored by a Republican administration.” Until and unless that judgment of the Iraq War is revised over time, in the minds of many they will remain as Parliament perceived America’s privateers in 1776—opportunistic “pyrates.”

The Continental Navy, notwithstanding the exploits of John Paul Jones, was a non factor in determining the Revolution’s outcome; competition from privateers robbed it of the ships and manpower needed to become a decisive force. The army likewise never did much “in the land way” except hold out long enough for France to make up its mind to formalize an alliance with America.

George Washington, ever the realist, acknowledged early in the conflict that his best strategy was “to sink Britain under the disgrace and expense” of slogging through to victory. Simply surviving against the vaunted British military was a brilliant feat involving countless small- and large-scale offensive operations to keep the enemy off balance, under strain and demoralized. But essentially the Continentals won by not losing.

The privateers, by contrast, carried the war to Britain. Their ravages on British trade panicked the public, hammered the economy and humiliated the crown. “We expect to make their merchants sick of a contest in which so much is risked and nothing gained,” Franklin had predicted in early 1776. Thanks to the privateers, Americans were soon encouraged to learn that British businessmen were ready to throw in the towel, urging the king to negotiate “an accommodation with the colonists upon commercial principles.”

The Continental Navy captured 198 enemy vessels all told. As for the privateers, conservative estimates place their haul at 2,300. At least 600 of their prizes were settled in American courts; countless others were tried abroad, retaken by the British or lost somewhere at sea. Edward Stanton Maclay, the first serious chronicler of Revolutionary privateering, wrote in 1898, “It is very much to be regretted that many of the cruises and actions of these craft have not been recorded.”

Maclay was an unabashed cheerleader for his subject. “Had it not been for our privateers, the Stars and Stripes would have been completely swept from the seas.” His counterparts among historians of the Continental Navy have been compelled to be more circumspect. William M. Fowler Jr. ends his book, Rebels Under Sail, on an almost bashful note: “If the Continental Navy had never existed, it is hard to see how the outcome of the Revolution could have been any different.”

The Continentals lost 832 men in ocean combat. Harder to measure is the number killed among what the U.S. Navy’s compilation of Revolutionary documents describes as that “peculiar comrade-in-arms, the privateers.” But statistics out of the coastal towns of Essex County, 30 miles north of Boston, offer a clue.

Newburyport listed 22 vessels destroyed and a thousand men dead. Nearby Salem lost almost one-third of its 54 registered privateers. Gloucester lost all 24. Their postwar populations of adult males were roughly half what they’d been before the war. Two-thirds of Beverly men between 18 and 60 were taken captive off privateers by the enemy. One-third of the women in Marblehead were widowed, and more than one-fourth of the children were fatherless. Hundreds of tax abatements were granted to families whose breadwinners were listed as “missing at sea,” “taken and sick,” “died abroad,” “in the hands of the enemy” or “long absent, supposed to be lost.”

Roughly 10 percent of all privateers seized by the Royal Navy hailed from Essex County. Private warships also poured out of “privateering mad” Boston and other New England ports as well as Maryland, Virginia, the Carolinas, the West Indies and Europe. But if wider consequences can be inferred from one county’s experience, it’s clear that untold thousands died in the enterprise.

The government editors of Naval Documents of the American Revolution acknowledge: “Hundreds of sea fights occurred between our privateers and British merchantmen, between United States and British privateers, and between our privateers and British naval vessels, but all such actions we have omitted. Privateers were not part of our navy.”

To judge from what a columnist in the Los Angeles Times called the “scalding gusher of animosity” that the Baghdad shooting incident brought down on Blackwater last fall, it seems Iraq’s security contractors will inherit the same historical dismissal that befell our Revolutionary privateers. For both, respect has been hard to come by, though in the case of the privateers—and who knows, perhaps for the Iraq contractors as well—perceptions do change over time.


Originally published in the June 2008 issue of American History. To subscribe, click here