Additionally and to compliment the excellent and extensive narrative written by Billy Mister on his and to the many descendants, the myriad times over great grandfather Marmaduke Mister (1722-1798). Billy put a lot of time and effort into doing his research where we all benefit and are in debt for his sharing with family, friends and those interested. Weat“Skipjack Heritage” endorse his writings, take nothing away and only contribute a few things to his narrative. We aim to expand on not only the Mister's, Wheland and others aforementioned, but expand on a few Loyalist, Picaroon, Tory Pirates to the Chesapeake and true stories as they relate to British and Loyalist plunder not yet mentioned and taken prisoner from the lower Delmarva.

It should also be observed that a substantial portion of the present-day population of Smith Island descends from the relatively small number of early families who first settled these isolated islands and marshlands as frontier homes. Bound together through generations of kinship, geography, and maritime life, these communities developed a distinct cultural identity shaped as much by isolation and self-reliance as by outside political events.

Within that context, Loyalist—or “Tory”—sympathies among some island families may be understood less as outright devotion to the British Crown than as resistance to the sweeping political and social changes promoted by the Whig revolutionary movement. For many Chesapeake watermen, loyalty to Britain represented continuity, stability, and preservation of long-established economic and maritime relationships upon which their livelihoods depended.

The Revolution brought disruption to trade, local governance, property rights, and traditional patterns of commerce throughout the Chesapeake. In isolated communities where survival depended heavily upon access to waterways, British markets, and maritime exchange, the revolutionary cause may have appeared uncertain, disruptive, or even threatening to established ways of life. Retaining the British connection therefore offered, to some, the prospect of preserving familiar institutions and economic security rather than embracing an unpredictable political transformation.

At the same time, allegiance in the Chesapeake was rarely absolute. Families and individuals frequently adapted according to circumstance, geography, kinship ties, and immediate survival. The marshes and islands of the lower Chesapeake produced not rigid ideologues, but pragmatic people navigating an unstable and often dangerous world where political identity could shift as quickly as control of the surrounding waters.

Many loyalists, tories, pirates famous and obscure frequented the Chesapeake Bay in the 17th and 18th centuries and preyed on those trying to survive. In general we discover..........Edward Teach- Blackbeard, Captain Kidd, Stede Bonnett, Edward Davis and Captain Cook. Bartholomew Roberts - Black Bart, Roger Makeele, William Claiborne, Captain Roache, Smith Carmine and many other lesser-known pirates prior to the Loyalist, local tory picaroons in the Chesapeake Bay.

The cause for independence was not universally popular on the Eastern Shore of Maryland or Virginia. Among those most committed to the Patriot cause on the Chesapeake mainland were many of the larger landowners, merchants, and planters—the affluent gentlemen who had long dominated county politics and commerce. To many isolated islanders and poorer watermen, these mainland elites often seemed distant from the realities of life on the marshes and islands, where survival depended less upon political theory than upon tides, weather, and access to the waterways.

Throughout much of the Revolution, island communities along both the Maryland and Virginia shores frequently found themselves exposed and inadequately defended. Caught between British naval forces, Loyalist picaroons, and at times even Patriot authorities, many islanders experienced the war less as a struggle over ideology than as a period of instability, confiscation, and vulnerability. The marsh islands of the lower Chesapeake became contested ground where ordinary residents often had little protection from whichever force happened to control the Bay.

Even Patriot measures could impose severe hardships upon local watermen. Virginia Governor Thomas Jefferson reportedly ordered that the boats of local watermen be seized and placed under guard in an effort to prevent their use by British forces. While militarily understandable, such actions threatened the livelihoods of island families who depended almost entirely upon their vessels for fishing, transportation, trade, and survival.

At the same time, British forces operating throughout the Chesapeake captured or recruited many local islanders—including enslaved people and free watermen—whose intimate knowledge of the Bay proved invaluable. Experienced pilots familiar with the Chesapeake’s shoals, guts, creeks, marsh passages, and hidden anchorages became essential to British naval operations.

Among them was Job Parks of Smith Island, born in 1758, who was reportedly taken by the British and later served as a pilot guiding British vessels through the Chesapeake. Like many others drawn into the conflict, his story reflects the complicated realities faced by islanders whose maritime skills made them valuable to whichever side controlled the waters at a given moment.

Such experiences help explain why allegiance in the lower Chesapeake was often fluid and pragmatic rather than ideological. For many island families, loyalty was shaped not by abstract political principles alone, but by immediate concerns of protection, livelihood, kinship, and survival in a region where control of the water frequently mattered more than proclamations issued from distant capitals.

I. Every man has a vote in affairs of moment; has equal title to the fresh provisions, or strong liquors, at any time seized, and may use them at pleasure, unless a scarcity makes it necessary, for the good of all, to vote a retrenchment.

II. Every man to be called fairly in turn, by list, on board of prizes because, (over and above their proper share,) they were on these occasions allowed a shift of clothes: but if they defrauded the company to the value of a dollar in plate, jewels, or money, marooning was their punishment. If the robbery was only betwixt one another, they contented themselves with slitting the ears and nose of him that was guilty, and set him on shore, not in an uninhabited place, but somewhere, where he was sure to encounter hardships.

III. No person to game at cards or dice for money.

IV. The lights and candles to be put out at eight o'clock at night: if any of the crew, after that hour still remained inclined for drinking, they were to do it on the open deck;

V. To keep their piece, pistols, and cutlass clean and fit for service.

VI. No boy or woman to be allowed amongst them. If any man were to be found seducing any of the latter sex, and carried her to sea, disguised, he was to suffer death;

VII. To desert the ship or their quarters in battle, was punished with death or marooning.

VIII. No striking one another on board, but every man's quarrels to be ended on shore, at sword and pistol.

IX. No man to talk of breaking up their way of living, till each had shared one thousand pounds. If in order to this, any man should lose a limb, or become a cripple in their service, he was to have eight hundred dollars, out of the public stock, and for lesser hurts, proportionately.

X. The Captain and Quartermaster to receive two shares of a prize: the master, boatswain, and gunner, one share and a half, and other officers one and quarter.

XI. The musicians to have rest on the Sabbath Day, but the other six days and nights, none without special favour^.

Under cover of darkness, raiding parties frequently sailed from their island strongholds to plunder farms and waterfront homes along the Eastern Shore before retreating by dawn into the labyrinth of marshes, creeks, and hidden channels surrounding Tangier Sound. The shallow-draft barges used by the picaroons allowed them to strike quickly and disappear into isolated island refuges beyond the immediate reach of mainland militia forces.

One of the clearest examples of these raids involved the attack upon William Roberts of Dames Quarter—an ancestor of the author—by the loyalist picaroon Joseph Wheland and his crew. Roberts was reportedly a wealthy and influential landowner in Somerset County, holding more than 1,500 acres in the Dames Quarter and Mount Vernon areas. His prominence, combined with local political tensions and at least one known personal vendetta among Wheland’s associates, appears to have made him a particular target.

According to surviving accounts, Wheland’s men descended upon the Roberts household during the night, forcibly abducting William Roberts from his bed, binding him, and carrying him away prisoner. The raiders reportedly plundered the property extensively, seizing enslaved people, livestock, food stores, household goods, and personal possessions before escaping back toward the islands under cover of darkness.

Notably, although salt was among the most valuable commodities in the wartime Chesapeake—essential for preserving meat and sustaining both civilian and military populations—there appears to be no specific mention of salt being taken during the raid. Surviving accounts likewise do not indicate that Roberts’ wife or family were physically harmed, though the psychological and financial devastation inflicted upon the household must have been severe. It also remains unclear how much physical abuse Roberts himself endured while in captivity.

The attack upon the Roberts family was not an isolated incident. Only a few nights later, the picaroons reportedly burned the home of Samuel McChester, further illustrating the climate of fear and instability that gripped portions of the lower Chesapeake during the Revolution.

Such raids reveal that the conflict along the Eastern Shore often resembled irregular frontier warfare more than conventional military campaigning. Personal grudges, political loyalties, economic opportunism, and local rivalries frequently merged together in violent nighttime attacks carried out by men who often knew their victims personally. In the marsh country of the Chesapeake, the Revolution became not only a war between Britain and the colonies, but at times a deeply local and intimate civil conflict between neighbors themselves.

William Roberts says his home was much hurt by the enemy as were other buildings (barns, meat-smoke houses, slave quarters, barns, stalls for his livestock and such) on his plantation-estate. Tory Pirates Joseph Wheland from Garden (?) Island was one of the most notorious leaders.  Marmaduke Mister, another direct ancestor to the author, was one of Whayland’s captains, as well as family members Stephen Mister, John Evans, Basil Clarkson, Richard Evans, etc. They operated as privateers for the British and caused much fear and depredation. These rogues sought to seek revenge on William Roberts who was an enemy of one of Wheland’s crew (Marmaduke Mister, John Evans, etc.?) Revenge for what is never said. Whether William Roberts was politically active with the Whigs is not known to the author?

The Governor of Virginia declared the Bay is so full of pirates it is impossible for any ship to go home safely.

The waters off Deal Island, then known as “Devil’s Island,” a dark, notorious name that identified the area as being macabre and sinister by many of those who had inhabited it were the site of many battles and threats between countians and the British invaders. In the 1800’s as an appeal to Christian (Methodism being the main denomination) sensitivities “Damned Quarter” was renamed “Dames Quarter” and “Devil’s Island to Deil’s Island.”

The reference to “Damned Quarter” near Devil’s Island is particularly evocative because many of these marsh localities acquired grim reputations during the war as hiding places, landing points, or detention sites associated with picaroons and loyalist refugees. “Rogues Point” on Smith Island was also renamed to Rhodes Point. Devil’s Island earned its name supposedly because it was a hideout for pirates, outlaws, rogues and a shipwrecked crew who washed up on its shore in the 1600’s before the picaroon’s and the British.

Plagued continually by the British, deviled from within by the picaroons, Smith Islanders feared for their lives as the British and picaroons continued to torment them, those close to the shoreline on mainland or lived off the many guts and creeks even though King Richard Evans had made an agreement. George Pruit of Hog Neck (Smith Island) had his house burned by picaroons for refusing to comply to their demands as setting an example to others who did not cooperate. There were always new and independent young rogues who did not honor or knew of any agreement in regard to providing food and victuals to the tory pirates so that the residents would come to no harm. One young roe, John Evans of Smith Island was heard to say that he was determined to have several of the principal people on the island dead or alive or at least get some of their negroes.

The islands and marshes of Tangier Sound became a refuge for a volatile mixture of loyalists, escaped slaves, fugitives, deserters, and picaroons during the Revolution. Many formerly enslaved men joined British forces not only seeking freedom from American bondage, but also because their intimate knowledge of the Chesapeake’s shoals, creeks, and hidden harbors made them indispensable as pilots and guides. Armed loyalist barges under men such as Joseph Wheland preyed upon local commerce throughout Hooper Strait and the surrounding sounds, blurring the line between naval warfare and piracy. To patriot authorities they were traitors and marauders; to many isolated islanders they were simply the power that controlled the water.

The estimate that tens of thousands of enslaved people escaped to British lines during the Revolution is historically supported. After Lord Dunmore’s 1775 proclamation in Virginia promised freedom to enslaved men willing to support the British cause, many enslaved people throughout the Chesapeake seized the opportunity to flee plantations and seek protection aboard British ships or within loyalist enclaves. Some served as soldiers, laborers, pilots, guides, sailors, or informants. Their knowledge of the Chesapeake’s dangerous shoals, marsh channels, creeks, and hidden anchorages made them extremely valuable to British naval operations.

Many Black pilots and watermen understood the Chesapeake better than Royal Navy officers themselves. They guided British vessels through shallow waters around Tangier Sound, Hooper Strait, Smith Island, Deal Island, the Annemessex, and the labyrinth of marshes that outsiders found difficult to navigate. They also identified fresh water sources, provisions, hidden landings, and sympathetic households.

At the same time, freedom under British protection often remained conditional and uncertain. Many who escaped bondage traded one form of dependency for another under British military authority. Some eventually gained permanent freedom after evacuation to Nova Scotia, Bermuda, England, or Sierra Leone, while others faced hardship, disease, re-enslavement, or abandonment after the war.  The account of the schooner Greyhound being seized in Hooper Strait by Joseph Wheland (often spelled Wheland or Wayland), John Evans, John Price, and others fits the documented pattern of loyalist picaroon raids in 1781–1782. Wheland’s barges and armed shallops regularly intercepted small commercial craft carrying provisions through the sounds. Cargoes such as salt, peas, bacon, and dry goods were especially valuable because they supplied both British forces and loyalist refugee communities.

Colonel George Dashiell of Somerset County warned Maryland Governor Thomas Johnson that the lower Eastern Shore was under continual harassment from British forces and local loyalist picaroons operating throughout the Chesapeake marshes. Somerset, Dorchester, and neighboring counties suffered repeated raids, thefts, and seizures carried out not only by British auxiliaries, but by local residents loyal to King George III who possessed intimate knowledge of the waterways.

Among these men was Stephen Mister, believed to have been born about 1745, the son of Abraham Mister and Alice Keen of Hoopers Island on the Honga River. Stephen served under the loyalist picaroon Joseph Wheland before striking out independently around 1779, operating an armed barge from bases along the Annemessex River. Familiar with the hidden creeks, shoals, and marsh channels of Tangier Sound, Mister and similar loyalist raiders blurred the line between privateering, guerrilla warfare, and outright piracy upon the Chesapeake Bay.

To patriot authorities they were “tory pirates” and traitors. To many isolated loyalist islanders, however, they represented protection, survival, and resistance against a revolutionary government that exercised little real control over the waters of the lower Chesapeake.

His exploits took him from the mouth of the Nanticoke River into the Tangier Sound where he not only plundered plantations, but shanghaied boats for use by the British. These boats were dispatched to Smith Island where Stephen’s uncle Marmaduke Mister who lived on the island were held until the British Navy arrived. Popular legend says that Marmaduke was rewarded for his services in picaroon treasure and that treasure is still buried at Kizzie’s Point. Two of the shanghaied boats captured by Joseph Wheland, Marmaduke Mister, John Evans and others along with its captain we find a Moses Yell and a Mr. Joseph White whose sloop had been dismasted when captured on the Nanticoke River and is recorded in the Maryland Archives. Joseph Wayland (Whayland, Wheyland, Wheland) wanted the mast from Yell’s boat to put in the sloop he captured from Joseph White. Wayland was going to turn the sloop into a tender with four four-pounders and twelve swivel guns to guard the Islands and keep the Shirt Men (Patriots) from going to abuse the Smith Island inhabitants. Before this could be done Wayland received orders from British Lord Dunmore to rejoin the fleet and thus it was burned.

Richard Evans’ agreement to provision the picaroons under Marmaduke Mister was likely less an act of loyalty to the Crown than an act of survival. Isolated island families during the Revolution frequently stood defenseless between patriot officials and armed loyalist raiders who controlled the Chesapeake waterways. Faced with the possibility of losing his property, livelihood, and perhaps the safety of his family, Evans appears to have negotiated a fragile truce: food and cooperation in exchange for peace. In the lawless waters of the lower Chesapeake, survival often outweighed political ideology.

The relationship between Richard Evans and Marmaduke Mister was not simply one of local resident and armed loyalist raider, but one bound by family ties. Richard Evans had married Judith Mister, Marmaduke’s sister, while John Evans married another sister, Hannah Mister, intertwining the Evans and Mister families within the small island communities of the lower Chesapeake. In such isolated maritime settlements, kinship often carried greater practical importance than distant political ideology.

Under these circumstances, Richard Evans’ reported agreement to furnish provisions in exchange for protection and non-interference appears less an act of outright loyalism than a negotiated survival arrangement shaped by family obligation, local alliances, and the harsh realities of war along the Chesapeake marshes. The lines between civilian, loyalist sympathizer, privateer, and picaroon frequently overlapped within these interconnected island families, where survival often depended upon cooperation with whichever force controlled the surrounding waters.

Marmaduke Mister, born 1722 (1732?) and named after his grandfather………………was one of Joseph Whayland’s (Wheland’s) crew and key captains who kept guard over the captured Captain Yell in a tender. [From the Maryland archives-] While aboard and guarding Captain Yell, Marmaduke asked Captain Yell whether he was for King or country? Captain Yell replied that he was a friend to every person that behaved well. Marmaduke then commanded in the Kings name to tell him the truth. Captain Yell answered telling him he was born in this country and had a right to defend his liberty. Marmaduke Mister then said what those damned rebels call liberty, I call slavery and so the people will find it. Marmaduke gained a reputation as being a ruthless Loyalist and pirate on the Chesapeake Bay who openly spoke out in favor of the British Crown.

Captain Yell (the deponent) further said that Marmaduke set fire to one of the vessels that was burned and was said to have the iron (nails, anchor, etc.) from or for doing it. Captain Moses Yell said John Evans, Roberts Howith and one Price were likewise aboard as well while under the command of Joseph Wheland. He also heard John Evans say he was determined to have several of the principal people on the islands (Smith Island, etc.) either dead or alive or get some of their negroes.

Additionally, Wayland had asked Captain Yell’s mate from whence he came and what he had in (Cargo). Joseph Mariman answered they were loaded down with plank and tar (wood and pitch) from the Hunger River headed back to the Potomack (Potomac) River. The plank and tar were to be put on board Richard Evans boat. Seems like Wayland was somewhat gentlemanly asking them if he was hungry? Wayland then ordered them to get in the canoe with the Mulatto fellow Lazarus and to go up to the three schooners and tell them to give him some victuals (supplies, food)

It was right after this occurrence that Joseph Wayland was captured in July in a small schooner inside a creek off Hoopers Straits. He was imprisoned in a log jail in Frederick, Maryland (as was Marmaduke Mister and John Evans from Smith Island- albeit some sources say that John Evans, Price and Howith posted bond).

Another account—somewhat of a side trail, yet closely tied to the broader pattern of British activity against local residents—concerns another ancestor of the author, John "Jackie" Roberts of Dames Quarter. He is buried at Rock Creek Cemetery, near Deal Island, Maryland.

According to genealogical records (including those cited by Find a Grave), there is strong evidence that Jackie Roberts was the son of Rencher Roberts, grandson of John Grandee Roberts, and great-grandson of Francis Roberts, the immigrant ancestor. His burial among members of the Webster family reflects the connections of his second marriage. He was born on June 3, 1762.

Surrounding him is a well-preserved family tradition recounting his capture by the British, his impressment into the Royal Navy, and his eventual escape and return to Somerset County, Maryland. This story was passed down through generations, with Reverend Emerson Pierce Roberts recalling how his father, William Underwood Roberts, retold it as he had heard it directly from his grandfather, “Jackie,” himself.

While elements of the story remain difficult to verify in full, its persistence across generations—and its consistency with known British practices of impressment during the Revolutionary period—lend it both credibility and historical value.

Credit the Chesapeake Bay Storyteller- Joe Pade

According to God’s Island: The History of Tangier by Kirk Mariner, another related account involves Job (“Joby”) Parks, likewise an ancestor of the author. During the severe winter of January 1780, Parks was taken prisoner by the British. Seizing an opportunity during an extraordinary cold spell—when the Chesapeake Bay and its tributaries had frozen—he made his escape near Devil’s Island.

With the waterways locked in ice, Parks undertook a difficult and dangerous journey on foot. He crossed the frozen Manokin River and traveled southward overland through Somerset County, Maryland. Reaching Flat Cap Point, just north of present-day Crisfield, Maryland, he continued his return toward home—navigating a stark winter landscape shaped as much by war as by nature.

Turning from his wartime activities to his personal life, Marmaduke Mister was married twice. His first marriage was to Rachael Evans, occurring between 1758 and 1760. Following her death or the dissolution of that union, he married Sarah Bradshaw sometime between 1770 and 1775.

With Rachael Evans/1744-1773 he had all girls including

• Sarah was born 2 June 1761
• Naomy was born on 13 January 1765 (5x great-grandmother, ancestor to the author)
• Charity was born 24 October 1767
• Betsey was born 17 September 1770

With Sarah Bradshaw/1744-1834 he had 2 boys including

• William was born 1777 (Born Accomac County, VA.)
• Severn was born 1785

On November 22, 1781, Marmaduke Mister and his brother-in-law John Evans—who had married Marmaduke’s sister Hannah—were released from confinement and permitted to return to Smith Island, Maryland and their families. The Maryland Archives (Vol. 48, p. 160) records that Marmaduke had been granted permission to return home after assisting in the transport of American prisoners from Tangier Island, Virginia.

By this point, his position in the war had clearly shifted. While Marmaduke was sailing under Patriot authority, his nephew Stephen Mister continued his plundering activities on the Bay. The contrast is striking—uncle and nephew on opposing sides of the same conflict. By the close of the American Revolutionary War, Marmaduke Mister was aligned with the Patriot cause.

Throughout the war, the Chesapeake was a contested and often lawless theater. Vessels carrying corn, pork, dry goods, and other provisions intended for the Continental Army were frequent targets. British forces, along with local Loyalist picaroons, intercepted many of these shipments, often profiting substantially. Some of these raiders are said to have returned to their strongholds—such as Dames Quarter—laden with goods taken from their own region.

In contrast, Marmaduke’s brother Abraham Mister, father of Stephen, remained firmly committed to the Patriot cause. On May 12, 1778, a correspondence to Thomas Johnson authorized payment of more than 133 pounds to Abraham Mister for transporting colonial troops in his vessel on at least five occasions—a substantial sum reflecting the importance of his service.

Peace, when it finally came, was welcomed—but the war had left a lasting mark on the isolated communities of the Chesapeake. With limited protection from naval forces and constant exposure to raids, island residents were forced into self-reliance. That inward-looking independence, shaped by necessity during the Revolution, would persist in the culture of places like Smith Island well into the twentieth century—and, in some respects, even today.

Tangier Island like Smith Island, Hollands Island, Watts Island, Somerset County Maryland (Dames Quarter, Deal Island, Annemessex, etc.) with all of its marshes, creeks and guts became the perfect tory base or more appropraite a hideout. On 13 April 1782 the Governor's Council presented a new set of sailing directions to depopulate the Tangier Islands within the limits of this State [Maryland] . . . This command was abandoned.

Because of their geography, Tangier Island, Virginia, Smith Island, Maryland, and neighboring islands such as Holland Island, Maryland were ideal havens during the Revolutionary War. The maze of waterways, guts, and creeks provided natural escape routes and concealment. These conditions fostered the rise of the so-called “picaroons”—often labeled Tory pirates—who operated in the gray space between privateering and outright plunder, shifting allegiance when it suited their survival or profit.

In later life, Marmaduke Mister appears to have undergone a profound personal transformation. Embracing Christianity, he became associated with the growth of early Methodist activity on Smith Island. According to Smith Island: Then and Now by Frances Dize, some of the island’s earliest Methodist gatherings were held in private homes, including that of Marmaduke Mister.

The first recorded religious service on Smith Island reportedly took place in 1808 at the home of Richard “King” Evans at Fogg’s Point. The following year, a three-day camp meeting was held at Old Orchard—also known as Kizzie's—where the island’s first church was later established. For years thereafter, services led by Joshua Thomas, remembered as the “Parson of the Islands,” were hosted in the home of Marmaduke Mister, the very man once associated with the Chesapeake picaroons.

Marmaduke is also said to have encouraged Thomas to settle on Smith Island. Given the close family and community ties among the islanders—particularly through the interconnected Evans and Mister families—it is likely the two men had known one another for many years. Through the influence of Joshua Thomas and the rapid spread of Methodism, the church came to shape nearly every aspect of life on Smith Island, influencing not only religious practice but also community identity, moral expectations, and local governance well into the nineteenth century. While describing the island as a true theocracy may overstate the case, the church undeniably occupied a central role in island society for generations.

In contrast, Stephen Mister appears never to have abandoned his loyalist and raiding activities. His ultimate fate remains uncertain. Surviving records indicate repeated arrests for treason in both Maryland and Virginia, suggesting he lived under continual threat of imprisonment or execution. Though it is possible he ultimately met his end at the gallows, no definitive record confirming such a fate has yet been discovered.

Marmaduke Mister’s own life closed under markedly different circumstances. In his will, dated October 10, 1796, he opened with the customary but revealing declaration, “thanks be to God… calling to mind the certainty of death.” He died on April 21, 1798. The will was witnessed by Richard Evans, Solomon Evans, James Spence, and William Thomas (Joshua Thomas' uncle), further reflecting the close-knit nature of the island community.

Perhaps most striking is the absence of any lasting punishment for Marmaduke’s earlier loyalist associations. Despite his documented connection to British-aligned raiders and picaroons, he was eventually allowed to return home, acquire property, and fully reintegrate into island life. By the end of his life, he appears to have become a comparatively prosperous and respected member of the community, remembered at least in part for his religious devotion and support of the Methodist movement.

Marmaduke Mister’s life illustrates the remarkable fluidity of allegiance and identity on the Revolutionary Chesapeake. Men could be, at different moments, loyalists, privateers, prisoners, patriots, and ultimately respected citizens. In Marmaduke’s case, he appears to have been all of these—a picaroon, a militia soldier, and eventually a reformed and God-fearing island patriarch shaped by war, survival, and redemption.

• In his “will” he directed a third of his personal property to be given to his second wife Sarah. Furthermore, he willed that Sarah have this land and marshes until his son Severn reached the age of twenty-one where and which time the land would be divided between his two sons William and Severn. The remainder was to be equally divided amongst all his children, including daughters who by now had all married.
• His will states.......... Marmaduke Mister of Somerset County in the State of Maryland, Planter.
• The two sons thrived from their inheritance.

Thomas B. B. Price, Jr., got the stone quotations, the shapes of the stones and their locations in the "Mister-Rowe Cemetery" on Deal Island. Here is the quote on the stone: "In memory of Sarah (Evans) Mister Consort of Marmaduke Mister who was born on Nov. 4, 1744 and departed this life July 7^th, 1834, aged 90 years, 2 mo. and 4 days. He was buried on “Deal Island” on what was reportedly the Severn Mister property. 

It is reasonable to conclude that Severn Mister likely benefited, at least indirectly, from the wealth accumulated through his father’s loyalist privateering and raiding activities during the American Revolution. Any proceeds retained from captured cargoes, livestock, vessels, or other plunder—particularly property not surrendered to British authorities or reclaimed by patriot owners—would almost certainly have circulated within interconnected family and community networks.

In the isolated and loosely governed world of the lower Chesapeake, where formal economic structures were limited and wartime oversight often nonexistent, illicit gains could be quietly converted into landholdings, maritime property, livestock, and commercial influence. Such wealth was difficult to trace and easily absorbed into local economies dependent upon barter, informal exchange, and maritime trade.

This context may help explain how Severn Mister later emerged as a substantial landowner and influential figure on Smith Island in the decades following the Revolution. While no surviving documentation directly ties specific acts of plunder to particular land acquisitions or holdings, the broader pattern is consistent with what is known of Chesapeake picaroon activity, where profits derived from wartime seizures were frequently transformed into property, economic stability, and social standing.

The trajectory of the Mister family reflects a larger reality of the post-Revolutionary Chesapeake: men associated with loyalist raiding and irregular maritime warfare were often able, over time, to reintegrate into local society, accumulate wealth, and establish respected family dynasties despite their controversial wartime pasts.

Whatever plunder that was not surrendered to the British the picaroonskept as given the circumstances, it is reasonable to conclude that Severn Mister benefited financially—whether directly or indirectly—from the activities of his father and the broader network of Loyalist raiders operating throughout the Chesapeake during the American Revolution. Wealth derived from the seizure of goods, livestock, vessels, and other property from fellow colonists, particularly that portion not surrendered to British authorities, could easily have remained within family and local networks. While definitive documentary proof linking specific acts of plunder to later holdings is limited, the pattern is consistent with the economic realities of the wartime Chesapeake, where illicit gains were often absorbed quietly into land, property, and maritime enterprise.

Severn inherited a substantial portion of the tract known as Pitchcroft on Smith Island, Maryland, deeded to him by his father upon reaching the age of twenty-one. He later expanded his holdings through the purchase of additional tracts known as “Purgatory,” “Barbadose,” and “Self-Preservation” from Thomas Rowe in 1814. By 1815, Severn had established a home on Deal Island, Maryland, further solidifying the family’s regional influence and prosperity.

In November 1839, Severn relocated to the western shore of Northumberland County, where he acquired a 539-acre property known as “Salt Pond.” Around this same period, the Deal Island home was conveyed to his son Bennett Mister, marking the gradual transfer of property and standing to the next generation.

The rise of families such as the Mister's, Evans reflects the complicated political and social realities of the Chesapeake during and after the Revolution. It has often been suggested that a considerable portion of the population along both the Maryland and Virginia Eastern Shores harbored Loyalist sympathies, though allegiance was frequently fluid and shaped less by ideology than by geography, commerce, kinship, and survival. In isolated maritime communities where British naval power often controlled the waterways more effectively than Patriot authorities, many residents adapted their loyalties according to circumstance and necessity rather than rigid political conviction.

Even today, on Smith Island, stories of Marmaduke Mister and the Loyalist raiders endure in local tradition and lore. Among the most persistent is the tale of his discovery of a cache of treasure attributed to the notorious pirate Blackbeard. According to island lore, the treasure was hidden deep within the marshes near Kizzie’s and has never been fully recovered. Generations of islanders have repeated stories of ghostly fogs drifting over the marsh at night, strange cries echoing across the reeds, and fortune seekers who supposedly uncovered the gold only to watch it disappear once more into the shifting mud and tides of the Chesapeake.

Whether rooted in fact, embellishment, or pure folklore, such stories reveal how deeply the memory of the Revolutionary era—and figures like Marmaduke Mister—remains woven into the cultural fabric of the Chesapeake Bay. Over time, the historical Marmaduke Mister whom hundreds to thousands who still live in the Lower Delmarva and other places has become something larger than the surviving records alone: part loyalist, part picaroon, part patriarch, and part folk legend lingering within the oral traditions of Smith Island and the surrounding marsh country.

Sources Cited:

• Virginia Commissioners Report, Boundary Line between Maryland and Virginia; R.F. Walker , Superintendent Public Printing
• Battle of Kedges Straits; Wikpedia
• Google Images
• History Between the Waters, The Battle of the Barges; Written by Bill Helin
• Archives of Maryland- Volume 17
• Pirates of Maryland; Mark P. Donnelly and Daniel Diehl
• Skipjack Heritage; Wes Simpkins
• History of Crisfield; Woodrow T. Wilson
• Old Offenders: Loyalists in the Lower Delmarva, 1775-1800; Timothy James Wilson