Exerpted with permission from Pirates on the Chesapeake, A True History of Pirates, Picaroons and raiders on the Chesapeake Bay 1610-1807 by Donald G. Shomette
We anchored in Chesapeake, after a most favorable passage, and the next day proceeded up as high as Lynnhaven." Thus wrote British General Alexander Leslie of his arrival in Bay waters with 2,500 soldiers aboard a strong Royal Navy task force on October 20, 1780. Leslie's orders were to destroy rebel munitions supplies at Richmond and Petersburg and to establish a permanent post on the Elizabeth River. For the picaroons of the tidewater, the presence of the British, especially the naval squadron commanded by Captain George Gayton, rekindled flickering loyalties to the Crown. Within days of Gayton's arrival, the lower and central Bay region, particularly in the vicinity of Tory hotbeds along the Eastern Shore, literally swarmed with the predatory barges, galleys, and privateers of the enemy. Some began to probe as high as the Patuxent on the western shore, while others contented themselves with penetration raids, plundering, and foraging into the heart of the defenseless Delmarva Peninsula.
For Maryland the enemy's return to the Bay came at a most inopportune time, for the state's naval defenses had practically ceased to exist. Never very large, by early 1780 the state navy force, with the exception of the little schooners Dolphin and Plater, had all been auctioned off. Virginia, against which the main thrust of the enemy was directed, was in near chaos as far as defense capabilities for the lower Bay. Now, suddenly, the Chesapeake was being subjected not only to the assault of powerful regular land and sea forces of the British, but also to the "numberless Depredations committed with Impunity by Picaroons.
One of the first targets on the revitalized picaroons' map was the Patuxent River, one of Maryland's most important and commercial waterways. Of its 110 miles, nearly 50 were accessible to seagoing ships of up to 300 tons burthen, and it sliced directly through the very heart of the western shore's richest, most productive tobacco-growing regions. The little towns dotting its banks, such as St. Leonard, Benedict, Huntingtown, Nottingham, Upper and Lower Marlboro, Pig Point, and Queen Anne's, were easily among the more prosperous in the central tidewater. Its waters were deep, its plantations numerous, and best of all for the picaroons, it was practically defenseless.
On November 5, 1780, the enemy finally entered the mouth of the Patuxent, probing only as high as Point Patience, a narrow finger of sand projecting into the river from the Calvert County peninsula. The raiders landed without warning on the point, burned the home of a local planter, John Parran, and seized two vessels laden with eighty hogsheads of tobacco. Retiring downriver, they sought provisions from Colonel William Fitzhugh's estate, Rousby Hall. Denied, they battered Fitzhugh's manor house to pieces with cannon fire, then burned what was left.
With the assistance of local Tory pilots from both St. Mary's and Calvert counties, the raiders hovered about the mouth of the Patuxent and Potomac for weeks on end, pouncing on any unsuspecting prey that sailed their way. The ad hoc blockade was so effective that on January 3, 178 1, Joseph Ford, Maryland Commissary of Purchases for St. Mary's County, complained to Annapolis that the "enemies Barges so closely watch Patuxent and Potomac Rivers, [that it] is too dangerous to send forward supplies. . ."
Among those Tories who had taken heart from the resurgence of Royal Navy power on the Bay was Joseph Wheland, jr., who had, after nearly five years of confinement, finally secured his freedom when a £10,000 bond was posted in his behalf at Baltimore by Samuel Covington and Thomas Holbrook. Wheland superficially appeared willing to reconcile his loyalist leanings, for in December he met with Colonel George Dashiell of Somerset County and sought to explain away his former actions. He had, he lied, indeed been concerned in attacks on patriot shipping, but it was only because he had been a British captive, in irons, and locked up below decks during actual fighting. He had been released and his boat was returned to him soon afterward. Now he chose to come up the Wicomico with his family to remove them from exposure to the picaroons. To prove his supposedly newfound loyalty, he told Dashiell he would even serve against the Tories and contribute to the expense of building a barge to be used against them!
George Dashiell was completely taken in by Wheland's story, and sent a letter to Governor Lee exculpating the crafty picaroon. Immediately afterward, he received an urgent express from Colonel Henry Hooper, commander of Dorchester County, requesting him to arrest Wheland, enclosing with the letter an affidavit from one Captain Valentine Peyton of Stafford County, Virginia. Peyton, it seemed, had been captured by Wheland on August 31 off Poplar Island. Soon afterward, Captain Oakley Haddaway's vessel had also been snapped up, as was one belonging to William Barnes. It seemed that the old picaroon had returned to his nefarious activities without batting an eye, in command of a white-bottomed pilot boat fitted with a jib, and a small crew of veteran Tories. Others of his kind followed suit. Among these was John Botsworth, a onetime ship's carpenter from Annapolis who had piloted British raiders up the Annemessex. Once, when a vessel Botsworth was piloting had gone into action against an American vessel, he had himself placed in chains so that in the event of capture he could claim he had been pressed into service. There were active loyalists from Holland and Tangier islands such as Thomas Prior and a desperado known only to authorities as Jack. Wheland was soon working frequently in close concert with the roaming armed barges of the British, passing secret signals of recognition when occasion demanded: three successive hoistings and lowerings of the mainsail, and then an English Jack raised at the masthead. He would soon become the undisputed king of the picaroons and gather about him a loyal following. Within a short time he had assembled a small but deadly flotilla of four barges, each of them commanded by himself or one of his trusted lieutenants, Shadrack Horseman or the brothers Michael Timmons and William Timmons, Jr., of Hooper's Strait.
Wheland's activities caused injury to friend and foe alike, even before he turned to outright piracy. On December 11, Samuel Covington and Thomas Holbrook were obliged to acknowledge themselves to be indebted to the State of Maryland for £5,000 each if the picaroon captain did not appear before Governor Lee and his Council "to answer a charge of high treason. Wheland, of course, failed to appear, and the bond was presumably forfeited."
By late fall 1780 there seemed to be no sanctuary for patriot shipping anywhere on the Chesapeake. "Several of the enemy's small armed vessels have recently," reported the Pennsylvania Gazette, "visited Oxford and other places on the Eastern Shore, Poplar Is1and in the Chesapeake and the Mouth of the Patuxent, on the Western Shore of this State, at all of which places their crews committed the greatest outrages. Not content with plundering the inhabitants of their Negroes, cattle and other property, they savagely laid several of their inhabitants in ashes."
On January 11, 1781, the Maryland Council learned that the notorious traitor Benedict Arnold, taking up where Alexander Leslie left off, was at the head of an army said to be nearly three thousand strong. He had taken Richmond and had sent a sizable force to capture Petersburg. The state of Virginia was, of course, panic-stricken. Towns on the Rappahannock and the Potomac, such as Fredericksburg and Alexandria, feared imminent attack. Maryland warned its county commanders that invasion of the state was expected. Relay systems were set up along the Potomac to warn of the enemy's approach. And the enemy did approach.
On January 22 a British frigate drove three Maryland State chartered vessels ashore, two of which were destroyed, at Cedar Point, near the mouth of the Patuxent. Raids were carried out on plantations at Point Lookout and Smith Creek, on the Potomac. A schooner was seized and burned several days later on the St. Mary's River. More raids were carried out in St. Mary's County.
The spate of plundering and foraging attacks continued unrestrained on the Eastern Shore as well as on the western shores of the Bay, and Joseph Wheland seemed to be in the thick of it. Colonel Joseph Dashiell of Worcester County, apparently aware of the Tory's release on bond, was more than a little upset over his inauspicious reappearance. On March 4, Dashiell wrote in irritation to Governor Lee:
Joseph Wheland that old offender is down in Somerset plundering again and we have reason to believe that the Gaoler in Baltimore is alone to blame as Wheland's Father informed one of our Neighbours that he let him go at large sum time before he Came away if this practice is followed no one will venture to take any of them up and send them forward as they will be there to suffer for it. If I had Directions to go into Somerset, I think I could apprehend him, as he has lately robed a certain Thomas Reuker who I think would assist me to Trap him.
Dashiell was equally distraught over the nest of Tories on the islands in Tangier Sound. Citing the recent robbery of a local citizen, one Plannor Williams, by a band of nine picaroons from the sound, he volunteered to the Governor that whenever your Excellency & Council propose to Remove the people and stock of the Islands I should be Glad to assist with all my heart as I consider them at this time the most Dangerous Enemy we have to watch the Motions off—and am Certain if they Can do us no other Damage they will rob & Plunder all they Can before they are removed.
Neighboring Somerset County was being constantly savaged by hit-and-run raids, for which Dashiell repeatedly blamed British cruisers, and more often than not, the picaroons from the larger islands in the sound. On Saturday morning, March 10, he was right on both counts, when a joint privateer-picaroon expedition once again assaulted the town of Vienna.
The invaders approached the town by water, coming up the Nanticoke in a brig and two sloops, one of them newly built and armed with fourteen 18-pounders. They began their attack with a heavy bombardment of the town, firing both round and grapeshot. A few resolute militiamen, commanded by Colonel John Dickinson and Captain William Smoot, gathered along the riverbank to stand their ground. When an enemy barge loaded with men rowed toward the shore, the defenders opened up with a brisk fire on them. Three times the enemy attempted to land, and three times they were beaten back. Finally, the intense fire from the shipping drove the militiamen back, and the barge reached the shore, though not without loss on both sides. Three of the attackers were wounded and one was killed, while the defenders suffered one killed. Soon after the enemy drew up on the shore, a flag of truce was forwarded to the militiamen. The attackers said they wanted nothing more than the grain stored in the town. If the militiamen would give it up, the invaders would leave a part of it for the inhabitants and would plunder nothing more. They promised to pay the market price for the grain, but if the defenders refused to agree to the deal and resumed hostilities, the town would be burned to the ground and everything in it destroyed. Colonel Henry Hooper, who had apparently arrived on the scene just before the landing, reasoned that as his force "could defend nothing, the Town and Grain lying under the command of their Vessels we agreed to their Terms."
The raiders carried off between 900 and 1,000 bushels of Indian corn before the eyes of the militiamen. While the flotilla lay at anchor, Hooper learned that another privateer brig guarded the mouth of the river, preventing possible relief or rescue by water. Speaking to several of the enemy, he discovered that they were actually foraging for Benedict Arnold's forces in Virginia. The invaders expressed disappointment that there had not been more grain stored in the town. They hinted broadly that they might next try the Choptank or Wicomico rivers for additional grain supplies. Since there was also a serious need for planks to complete the construction of some forty flat-bottomed boats being built at Portsmouth, they were also in the market for lumber boats. In fact, much to Hooper's chagrin, they had already captured two or three during their short visit to the Nanticoke! On Monday morning the invaders, having honored their word, and to Hooper's great relief, departed.
Colonel Joseph Dashiell, whose hands were quite full resisting landings from the raiding cruisers and barges on Worcester County shores, was deeply angered over the surrender of Vienna and blamed Hooper for the militia's retreat under fire. The Lieutenant of that County arrived and ordered the Militia to retreat as I am told, & has made a Capitulation that in my Oppinion will Disgrace us, & be attended with the worst Consequences."
British depredations continued without letup in the Bay. The port of Annapolis was blockaded by enemy warships. The Elk River area was threatened. Landings were carried out on Poole's Island and in Harford County, and the Maryland state government rushed to mobilize. Scenes of chaos and disorder were repeated throughout the central and upper Bay region—a schooner run ashore by Tory barges here, a refugee with all his belongings forced to flee before the marauders there, and everywhere looting, homes burned, and waterborne commerce throttled by picaroons, privateers, and the Royal Navy.
By early April Maryland's two principal waterways, the Potomac and Patuxent, were being brutally hit almost simultaneously. On Saturday, April 7, a picaroon barge, manned principally by blacks but commanded by Captain Jonathan Robinson, a white man, probed far up the Patuxent, causing the local population along the banks no end of despair. Within a short time of the alarm, riverfront homes from Swanson's Creek northward to Upper Marlboro were totally abandoned in an atmosphere of panic. The picaroons proceeded as high up as Lower Marlboro, where they landed unopposed and promptly plundered the town. The home of Captain John David, former commander of the Maryland State galley Conqueror, along with an unsuspecting traveler sleeping inside, was burned to the ground. Colonel Peregrine Fitzhugh and William Allein, a local merchant, were taken prisoner but later released. All of the vessels lying before the town, including one fully laden with provisions, were captured. The tobacco stores in the local warehouse were entirely plundered. On Sunday morning, the raiders, satiated by their robberies, set off down the river, with a strong northwest wind behind them and a large band of slaves belonging to Colonel Fitzhugh, now freed from their bondage.
"Every hours experience," wrote Stephen West, a leader and civic bulwark of the Patuxent mercantile community, "shows the necessity of having some Armed Vessels in the great Rivers especially the Patuxent and Potowmack." His prognosis was underscored almost immediately, for the barge escaped unscathed and on the day following the raid rendezvoused with two ships and a brig at the river's mouth. That evening, the barge landed a few miles to the south at Cedar Point on the Bay, and its occupants ruthlessly burned the home of Nicholas Sewell, an ardent patriot of St. Mary's County.
Similar depredations were carried out by enemy privateers on the Potomac. Probes were carried out as far upriver as Alexandria, followed by a series of landings at various places along both shores of the river. Homes and plantations were plundered and burned, slaves stolen, and innocent civilians carted off as prisoners. At Young's Ferry, Hooe's Ferry, Robert Washington's plantation, and Port Tobacco they came ashore and conducted their nefarious activities. Estates such as Walter Hanson's, the "Elegant Seat" of George Dent, and others fell victim. Local militia units seemed powerless to stem the assaults. At Alexandria the militia mustered, and the foe turned his attentions to the Maryland shore. There too, opposition congealed only to fall away under heavy attack.
Finally, about the latter part of April, the raiders withdrew, the holds of their ships and barges filled with plunder. It had been a miserable experience for Maryland and Virginia, both of which had been entirely unprepared to meet the emergency. "I expect we shall have frequent visits from these plundering Banditts, " wrote Thomas Stone of Maryland after the raiders' departure. "I hope we will so well prepare as to repel their attacks that they will find the business as unprofitable as it is disgraceful."
It was a vain hope.
Despite the best intentions of the nearly impotent Maryland government to blunt the amphibious depredations of picaroons and privateers, it was becoming painfully evident that the burden of naval defense—until the State Navy might be revitalized and operational would have to fall on regional self-defense efforts. The Eastern Shore, isolated from the center of state government and frequently cut off from outside help, was particularly vulnerable. "Local circumstances render it Difficult," wrote two Dorchester County leaders, Robert Goldsborough and Gustavus Scott, "for the Inhabitants of this Shore, exposed as they are to the utmost Calamities of War & Piracies to expect assistance from our more powerfull neighbours of the western shore." Dorchester County, with 1,700 effective fighting men (of which only 150 were armed), reflected the deadly vulnerability to attack of all the Eastern Shore counties without naval protection."
One of the first major efforts to address the issue of regional defense in the absence of a state navy force was in Somerset County. On March 21, 1781, twenty-six of the county's leading citizens, stirred to action by the mounting attacks against their region by picaroons and privateers, proposed to the Maryland Council a scheme fathered by Captain Zedekiah Walley. Walley's plan was to build a barge of 50-foot keel length capable of carrying 60 men and a 24-pound bow gun to protect county waters. Such a vessel might be built for less than £150 hard money, and Walley himself volunteered to superintend the construction. Though the state was sympathetic to the proposal, there was virtually no money in the treasury. Somerset Countians, therefore, went ahead on their own with the project. Built at Snow Hill, the barge was dubbed Protector. She was destined to sail with great success, on one occasion even driving the picaroon raiders from the Pocomoke region and capturing several prizes. Soon, taking heart from Somerset's self-reliant stance, Queen Anne's and Talbot counties offered to support and maintain a barge called Experiment, and to build a number of boats for their own protection. These vessels would be stationed in Eastern Bay and would cruise occasionally between Kent Point and Tilghman Island. Dorchester County followed suit with the construction of the barge Defence. Eventually, more barges, either captured from the enemy or finally constructed for the state government, began to appear in Bay waters, vessels with names like Intrepid, Terrible, and Fearnaught.
On the western shore, the first area to consider a local naval defense force and a policy of its own were the counties bordering on the Patuxent River, but principally Prince George's and Calvert counties. It had been apparent, even before the Lower Marlboro raid, that the Patuxent needed a standing defense system to counter picaroon incursions. Driven, like their counterparts on the Eastern Shore, to desperation, twenty-three merchants and gentlemen of Calvert and Prince George's counties convened a meeting at the river port of Nottingham on April 21. There, they set in motion a plan to raise their own naval defense force. Calling themselves the Board of Patuxent Associators and led by Colonel William Fitzhugh, the body was soon able to secure authority from the Governor of Maryland to manage their own regional defenses, impress vessels, move equipment, and protect the Patuxent.
Yet even as the Board of Patuxent Associators sought to improve the river's defenses against the picaroons, the battle raged on. On April 25, off the mouth of the river two American privateer schooners, Antelope, Captain Frederick Folger, and Felicity, Captain Cole, fell in with a New York privateer called Jack-a-Lanthorn, Captain Mangen, of six guns and thirty-six men, and a small prize sloop. The two American privateers had already captured a British ship called Resolution in the lower Bay, and when they encountered and took the New Yorker, they not only relieved the Patuxent region of a potential attacker, but promised to enrich the coffers of their owners through the sale of their new prizes.
The Board of Patuxent Associators was frustrated by lack of funds, state support, and a paucity of armament, supplies, and vessels. Yet the members pressed ahead. Artillery was mounted at strategic positions on the river. Beacons were erected at appropriate locations to provide early warning of intruders. And a move was set afoot to secure a row galley, a 40-foot-long armed barge, and a whaleboat to serve as look-out. A committee was sent to Baltimore to examine the recently captured Jack-a-Lanthorn for possible purchase, but the price was too high. On May 10, the Board's agents, Samuel Maynard and Renaldo Johnson, purchased a ship, a battered schooner called Nautilus, salvaged from the shoals of Cedar Point, where she had been run aground by a British warship in January. This vessel, of eighty-five tons burthen, was armed with eight 3-pounders and lay at Fells Point. The price was right, and an agreement was struck with her owners, Dorsey Wheeler and Company and Thomas Worthington. The ship was sold for 357,000-pound weight of tobacco. Captain John David of Lower Marlboro was charged with command of the vessel and with getting her down the picaroon-infested Bay to the Patuxent. Apparently, though, no one bothered to consult with David before assigning him the task, for he had already engaged to serve in another vessel. By the end of May Nautilus was still lying at Fells Point, Baltimore. A barge and a whaleboat had yet to be procured. When Nautilus finally did reach the Patuxent, her suitability as a guardship was apparently questionable, for on August 11 she was put up for sale at Nottingham by the Board. With the sale of Nautilus, the intended fulcrum of the Patuxent naval defense, the efforts of the short-lived Board of Associators to protect their river ended in abject failure.
The fear of an invasion of Maryland lingered like a dull headache throughout the early summer of 1781. County militia units were held in readiness to march at a moment's notice, and commissaries were directed to purchase or seize all stocks in the event of attack to prevent them from falling into enemy hands. Enemy warships appeared in the Potomac again in early June, dispatching armed barges on occasion to conduct foraging raids or simply to plunder and terrorize the civilian population. By mid-June the enemy had disappeared from the river, but the picaroons, hovering like birds of prey, frequently flew in to pick up the leavings.
In July, Joseph Wheland struck again. This time the victim was Greyhound, "a beautiful boat laden with Salt, Peas, Pork, Bacon and some Dry Goods." Captured in Hooper's Strait, the skipper and his crew were detained for twenty-four hours aboard Wheland's barge, during which time one of the passengers, a Mr. Furnival, was robbed of his money and watch "and indeed every Thing that the Thieves could lay their Hands on." The captain of the schooner and his men were set ashore at Dames Quarter. Before he was released, Furnival later reported, he "saw several other Bay craft fall into the Fangs of the same Vultures."
As the picaroon attacks continued unabated, pressure increased for the Maryland government to act. The region between the mouth of the Patuxent south to Tangier Sound had become a virtual no-man's-land through which shipping ventured to pass at its own great risk. In early July Samuel Smith of Baltimore informed Governor Lee that two of his vessels, commanded by James Rouse and Martin Trout (apparently chartered to the state to carry tobacco), had been taken. "This is a heavy loss to my business," he complained, as "they were taken just coming out of Patuxent by three Barges full of Men one of which went down & the other two up to burn Capt. [Jeremiah] Yellet's Brig."
From Salisbury, Joseph Dashiell informed the Governor that "there is four privetars and as many Barges in our sound they have plundered the Houses of Leven Gale & Levin Dashiell & Burned all the Houses of the Latter yesterday morning." Such reports flowed daily through the Maryland chief executive's office. Not only were picaroons becoming bolder, but the occasional barbarity of their actions seemed to be increasing as well. In mid-July Captain Gale of the Somerset County Militia was literally hauled from his bed by a protégé of Joseph Wheland, one Captain John McMullen, commander of the picaroon barge Restoration, accompanied by four white men and nine black men. The unfortunate militiaman was hauled off to Clay Island, "where he was most inhumanly whipt six lashes" and then hung until they believed him dead. Soon after he was cut down, he revived. McMullen attempted to persuade his crew to hang their victim again, but they refused. He proposed drowning the poor man, but again they refused. Finally, Gale was released after taking an oath not to bear arms against the King.
Wheland, McMullen, and Robinson frequently acted in concert now, occasionally rendezvousing at Courtney's Island before setting out upon a cruise. Wheland and his chief lieutenant, William Timmons, Jr., occasionally preferred the mobility of a small whaleboat to the larger barge, and visited the Wicomico or any other place along the Eastern Shore to their liking, defended or not, with relative impunity. They did not discriminate in the selection of their men, and frequently employed black slaves whom they had freed during their attacks as crewmen. Indeed, the black picaroons proved to be so ferocious in battle as to intimidate their white opponents, a trait that frequently played in Wheland's favor. Neither were the picaroons particular in the selection of their victims, be it a helpless widow or a patriot militia officer of local political or economic stature. Eventually, for Joseph Wheland, it wouldn't even matter whether his prey was patriot or Tory.
At last, in response to the picaroon and privateering depredations of the foe, Maryland fielded its first barge flotilla to cruise since the reduction of its Navy in 1778-1779. The flotilla's first expedition, initiated on July 28, 1781, was designed specifically to rid the Bay of the picaroons. Commodore George Grason of the Maryland Navy was given command. The flotilla was to be composed of the barges Intrepid, Captain Levin Speeden, Terrible, Captain Robert Dashiell, and Grason's own flagship Revenge. Two days after sailing, on July 30 , the little squadron engaged two picaroon barges, a whaleboat, and two smaller vessels. By chance they had fallen in with the leading pirates on the Bay, Wheland, Robinson, and McMullen. The barge Restoration, with McMullen, and two boats were taken. Robinson in the second barge, and Wheland in the whaleboat, were put to flight. Euphoria over this victory was contagious on the Eastern Shore. "The event has given general joy," wrote one Matthew Tilghman on August 3, "and if we cannot flatter ourselves with peace, we begin to think we have a chance of remaining safe from the plunderers that have late infested us."
The picaroons were not intimidated in the least and did not refrain from their attacks. In late August they again visited the Patuxent, leaving the river only after capturing three vessels laden with tobacco. On August 27 two barges pushed up the Nanticoke to Vienna, plundered the inhabitants of the town, and captured two or three fully laden vessels lying in the river there. One of the barges proceeded up beyond the town and captured two more vessels, even as her sister barge retired downriver with her prizes. Belatedly alerted, Colonel Henry Hooper collected a party of militia as quickly as possible and retook three of the vessels. Then, posting some men on each side of the river, he effectively cut off the retreat of one of the barges, forcing the enemy to run her ashore and make their escape on foot. Three picaroons were captured and sent to Annapolis on August 31. After securing the barge, Hooper dispatched a party of light horse down the river, but the second barge and her prizes had disappeared. Upon receiving a report from the party of light horse that the enemy's barge was not to be seen in the river, the colonel discharged the militia.
At one o'clock the following morning, Hooper received an urgent express that the barge had returned in the night and made the inhabitants of Vienna prisoners. Orders were issued for the militia to reassemble and march to the town. But it was already too late, for the elusive enemy had escaped once again.
Farther south on the Chesapeake, Tory and privateer raids were conducted with equally unvarnished bravado, though they were increasingly motivated, as the war dragged on, by a desire for the fruits of plunder rather than by patriotic devotion to the King and England. Occasionally, but with accelerating frequency, picaroon raids were conducted without discrimination against both sides. By the late summer of 1781 Gwynn's Island at the mouth of the Piankatank River was frequently being used as a picaroon base for barge operations—which were increasingly directed against fellow Tories as well as patriots. A number of picaroons had, in essence, degenerated from seaborne guerrillas to little more than out-and-out pirates, who plundered at will, when and whom they pleased. In mid-June, General George Weedon of Virginia wrote that some "of their vessels are continually in the mouth of the river and I am convinced from many circumstances hold a correspondence with . . . inhabitants of Gwyn's Island and Middlesex . . . " The loyalists of the region, as far away as Urbanna on the Rappahannock, a place patriots called a "sink" of Tory disaffection, were rapidly becoming disenchanted with their so-called waterborne allies. On June 19, it was reported that such notable and influential loyalists as Ralph Wormley of Rosegill, John Randolph Grymes, Beverly Robinson, and the inhabitants of Urbanna themselves had been plundered by Tory picaroons. When Wormley and Robinson assembled a band of loyalists at Robinson's estate, "to consult a plan of recovery," the picaroons struck again "and plundered them a second time, without landing at any other house...
The depredations of the pirate picaroons and privateers had by now disgusted the leaders of both sides. Even Lord Cornwallis, who had recently arrived at Portsmouth, Virginia, with his veteran army, was shocked by their vindictive activities and commented in a letter to Sir Henry Clinton, British Commander in Chief in North America, that the "horrid enormity of our privateers in the Chesapeake Bay" was quite "prejudicial to his Majesty's service." Indeed, it was driving some loyalists away from the Crown and hardening the resolve of the American cause.
Cornwallis, however, had more important matters to occupy his time than the dirty little guerrilla war on the Bay. He had an army to move, and a town to fortify—a little place on the York River called Yorktown. Tory picaroons, such as the likes of Joseph Wheland, Jr., were Maryland's and Virginia's problem.