Pirates of the American Revolution in the Chesapeake Bay: Joseph Wheland Jr. and the Loyalist Picaroons

By Jamie L. H. Goodall

The American Revolution is often viewed through a loyalist vs. rebel/revolutionary lens. On the one hand, there were the proud, patriotic American colonists, and on the other hand an oppressive and cruel king. Among the Americans were thousands of individuals who volunteered their time, their money, their vessels, and their lives in support of the Continental Navy and the revolutionary cause as privateers. These privateers were an important component in the war because of the lack of a strong, formalized naval force, but we can’t forget those privateers whose loyalties remained with King George III. The revolutionary Patriots had to contend not only with the Royal Navy, but with the Loyalists among them who operated as privateers for the British.[1] 

In October 1780, British General Alexander Leslie arrived in the Chesapeake Bay with 2,500 soldiers and a strong naval force with orders to destroy rebel munitions supplies at Richmond and Petersburg and to establish a permanent post on the Elizabeth River. If local Loyalists had wavered in their support for the king, their spirits were renewed with the arrival of Leslie and the naval squadron commanded by Captain George Gayton. The Chesapeake found itself relatively defenseless. Maryland’s state navy was all but nonexistent save for two small schooners, the Dolphin and Platter, and Virginia’s forces were depleted as they attempted to defend the entirety of the bay. It was the moment the picaroons, a term for pirates in the Chesapeake, had been waiting for.[2] They set their sights on the Patuxent River, one of Maryland’s most important and commercial waterways, encompassing 50 accessible miles that ran directly through the very heart of the western shore’s richest, most productive tobacco-growing regions.[3] Among the Loyalists newly emboldened by the arrival of the British was Joseph Wheland, Jr. Wheland was a “tall, slim, gallows looking fellow” who often wore a gold-laced jacket. His attacks were unpredictable. With each new success, Wheland gained the support of other Loyalists throughout the Bay. From the Patuxent River in the north to Tangier Sound in the south, these Loyalist picaroons raided with impunity.

Cover of Jamie L.H. Goodall's book "Pirates of the Chesapeake Bay: From the Colonial Era to the Oyster War."

Wheland got his start in 1776 just prior to the arrival of the British in 1780, although his activities increased after their arrival. In 1776, he had seized the ship of a local man named John White to outfit as his new vessel. He planned to add a total of sixteen guns in order to protect the Loyalists throughout the Bay from Patriot militiamen. In the meantime, he continued to plunder the eastern shore, coming across a ship laden with tar and planks. Before the vessel’s captain, Mores Yell, had time to react, Wheland and his men had taken control of the ship. Wheland disclosed that he had a commission from Lord Dunmore to “take any Vessel belonging to the Rebels and destroy such as he thought proper and carry the rest to the fleet.”[4] Wheland was far from done and continued his pirating. He and three of his men made for the Hooper’s Strait area. This time, they would face the wrath of the Patriots. A detachment under the command of Major Fallin received intelligence of Wheland being in the area and immediately set out to catch him. They seized Wheland’s ship and its cargo consisting of one and a half hogshead of rum, 30 bushels of salt, the sails and rigging of a sloop, and a large quantity of iron, guns, swords, and cartridges. After being captured, Wheland and his men faced many charges, including trading with Dunmore’s fleet, piratically burning John White’s sloop, and a host of other depredations. The evidence against him, particularly the deposition of Mores Yell, was incriminating. Wheland was ultimately found guilty of harboring strong Loyalist sentiments and a lust for profit from piracy. He was sentenced to jail time in Frederick County in 1776, far from the Chesapeake Bay until he was able to offer full restitution to John White and make bond for good conduct in the future.[5]

Wheland was released in 1781 after five years of confinement for piracy when a £10,000 bond was posted on his behalf at Baltimore by two local men of means who had benefited from Wheland’s depredations, Samuel Covington and Thomas Holbrook. The bond would be considered forfeited if Wheland failed to appear in court. Wheland then denounced his Loyalist leanings to Colonel George Dashiell of Somerset County and claimed he wasn’t a pirate, but a British captive. He promised to support the revolutionary cause and even offered to finance the building of a barge to be used against the British. Unfortunately for Daishell, he fell for Wheland’s ruse.[6] 

No sooner had Wheland been released when there was another call for his arrest. Colonel Henry Hooper, commander of Dorchester County, had evidence that Wheland had captured the vessel of Captain Valentine Peyton followed by the vessels of Captain Oakley Haddaway and William Barnes. It appeared that Wheland was back up to his old tricks; and he wasn’t alone. He amassed a small flotilla and became the undisputed king of the picaroons. Next, Wheland attacked a vessel in Hooper’s Straight called the Greyhound. It was laden with “Salt, Peas, Pork, Bacon, and some Dry Goods.” Wheland held the passengers prisoner for at least 24 hours, robbing them of every personal effect they had on them, including money and watches. Pirating and plundering continued unabated throughout the Bay with Wheland at the helm. Colonel Daishell wrote to Governor Lee “Joseph Wheland that old offender is down in Somerset plundering again…If I had Directions to go into Somerset, I think I could apprehend him, as he has lately robed [sic] a certain Thomas Reuker who I think would assist me to Trap him.”[7] 

One of Wheland’s major attacks in 1781 was against the ship of John Greenwood. Greenwood, at just 21 years old, had served in the Continental Army from Bunker Hill to the Battle of Trenton and then transferred to the Continental Navy. This was followed by a stint as second mate on a Boston privateer before he financed his own privateer vessel. Wheland forced Greenwood and his men to participate in a raid of Gwynn’s Island. When Greenwood referred to Wheland as a pirate, the picaroon took offense and claimed to have a good commission from the British to seize any vessels coming in and out of the Bay. When Greenwood and several of his men attempted to make their escape, Wheland sailed after them, firing shot after shot at Greenwood and his men. Fortunately for Greenwood, the picaroons were “such bad marksmen” they didn’t hit any of the men. Greenwood described the pirates as “a set of gallows-marked rascals, fit for nothing but thieves; hellhounds and plunderers from inoffensive, unarmed people, they seemed to be without any kind of principle.” He didn’t believe they were operating as real privateers with the sanction of the British government. According to Greenwood, Wheland appeared to be “as great a villain as ever was unhung, and all such characters the British seemed to encourage in their employ.” Ultimately, Wheland gave up the chase to search for new prizes.[8] 

Eventually, for Joseph Wheland, it wouldn’t even matter whether his prey was Patriot or Tory. Residents of the Bay pleaded with the governments of Maryland and Virginia to put a stop to his depredations. Colonel Daishell put together a flotilla to apprehend the picaroons consisting of three barges:  Intrepid, Terrible, and Revenge. The vessels had been commissioned after the 1780 passage of the Bay Defense Act in Maryland. If the names of the vessels were any indication, the Patriots of the Bay had clearly had enough of the picaroons and were ready to end them. In late July 1781, the flotilla set off on its first expedition, designed specifically to rid the Bay of the picaroons. Within two days of setting off, the barges encountered a picaroon flotilla led by none other than Wheland and two of his associates. The picaroons scattered and one of Wheland’s men was easily taken. Wheland fled, escaping the Patriot flotilla easily. But this victory brought great relief to inhabitants along the Bay, especially with the news that Wheland had left the Bay. Ultimately, Wheland and Robinson made their way to the Carolinas where they would be apprehended, putting an end to Wheland’s terror on the Chesapeake.[9]

Wheland’s activities provide us an important lens through which to view the American Revolution and the role of piracy during the war. His actions were particularly helpful to the British who were preoccupied with formal military matters. The Chesapeake Bay was a critical route for fast communications out of Philadelphia to the southern colonies, and Loyalist privateers like Wheland not only interrupted those communiques, but also threw the financial stability of Continental forces into turmoil. Additionally, the British were busy dealing with the American privateers who were called up by George Washington. Washington remarked, “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.”[10] The use of Loyalist privateers like Wheland helped to balance out the Americans’ devastations as Washington’s call for private seaborne insurgency ultimately proved instrumental in turning British popular opinion against the war.

Wheland also demonstrates the blurred line between the legally sanctioned privateer and the illegal commerce raider. Technically there were only two things separating a pirate and a privateer: perspective and a Letter of Marque. In essence, a Letter of Marque merely gave the act of piracy the facade of legitimacy. Privateers were little more than legally sanctioned pirates whose actions were clearly piratical under the rule of law, but which went purposefully unpunished. While privateering was often viewed as an honorable and patriotic duty (augmenting naval forces), piracy was widely considered a scourge on the seas. Officials tried these so-called privateers as pirates, refusing to recognize the Letter of Marque as legitimate, and executing them before anything could be done. Despite (supposedly) holding a good commission from the British, it’s clear that Wheland’s depredations crossed the line into piratical.

Jamie L. H. Goodall, PhD is a staff historian at the U.S. Army Center of Military History. She has a PhD in History from The Ohio State University with specializations in Atlantic World, Early American, and Military histories. She is also a first-generation college student. Her publications include a journal article, “Tippling Houses, Rum Shops, & Taverns: How Alcohol Fueled Informal Commercial Networks and Knowledge Exchange in the West Indies” in the Journal of Maritime History and Pirates of the Chesapeake Bay: A Brief History of Piracy in Maryland and Virginia (2020). She is currently working on a manuscript about pirates in the Mid-Atlantic. You can find her on Twitter: @L_Historienne.

Title Image: Ships in a Stormy Sea, mid-seventeenth–early eighteenth century by Ludolf Backhuysen, pen and brown ink, gray wash, over traces of black chalk. Metropolitan Museum of Art.

Further Readings:

Goodall, Jamie. Pirates of the Chesapeake Bay: From the Colonial Era to the Oyster Wars. Charleston, SC: The History Press, 2020.

Konstam, Angus. American Privateers of the Revolutionary War. Bloomsbury Publishing, 2020.

Patton, Robert H. Patriot Pirates: The Privateer War for Freedom and Fortune in the American Revolution. New York: Vintage Books, 2008.

Perl-Rosenthal, Nathan. Citizen Sailors: Becoming American in the Age of Revolution. Cambridge: Harvard University Press, 2015.

Shomette, Donald. Pirates on the Chesapeake, A True History of Pirates, Picaroons and raiders on the Chesapeake Bay 1610-1807. Tidewater Publishers, 2008.


[1] Jamie Goodall, Pirates of the Chesapeake Bay: From the Colonial Era to the Oyster Wars (Charleston, SC: The History Press, 2020), 56.

[2] In the lower tidewater area of the Chesapeake Bay, pirates became known as picaroons, coming from the Spanish picaron, meaning a rogue or scoundrel.

[3] Donald Shomette, “Pirates in Calvert County” excerpted from Pirates on the Chesapeake, A True History of Pirates, Picaroons and raiders on the Chesapeake Bay 1610-1807 (Tidewater Publishers, 2008). Accessed July 29, 2020, http://calvert-county.com/Pirates/pirates.html

[4] Goodall, Pirates of the Chesapeake Bay, 64-65; Donald Shomette, Pirates on the Chesapeake, A True History of Pirates, Picaroons and raiders on the Chesapeake Bay 1610-1807 (Tidewater Publishers, 2008), 261-263.

[5] Goodall, Pirates of the Chesapeake Bay, 66-67; Morgan, William James ed., “Deposition of Mores Yell, July 27th, 1776,” in Naval Documents of the American Revolution, Vol. 5. Washington: 1970, 1247-1248; Calendar of Maryland State Papers: Executive Miscellaneous, Vol. 5. Annapolis, MD: The Hall of Records Commission, 1958,  57-58.

[6] Goodall, Pirates of the Chesapeake Bay, 61; Shomette, “Pirates in Calvert County.”

[7] Goodall, Pirates of the Chesapeake Bay, 61; Shomette, “Pirates in Calvert County.”

[8] Goodall, Pirates of the Chesapeake Bay, 62-63; Shomette, “Pirates in Calvert County;” Greenwood, Jr., Isaac J. “Cruizing on the Chesapeake in 1781” Maryland Historical Magazine Vol. 5, No. 2 (1910): 123-125.

[9] Goodall, Pirates of the Chesapeake Bay, 68-69; Shomette, “Pirates in Calvert County.”; Calendar of Maryland State Papers: The Red Books, Vol. 4, No. 3, 119.

[10] “From George Washington to Colonel Benedict Arnold, 5 December 1775.” Founders Online. Accessed August 1, 2020, https://founders.archives.gov/documents/Washington/03-02-02-0444.

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