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Roger Michael - Eastern Shore's Own Pirate

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Roger Michael was born in about 1644 somewhere in England. He came to Virginia as a teenager. He is not listed as a headright in the local records of the time. That could mean that he was a seaman or a person of some means or that he had come from some other locale. In an effort to provide some insight into the disposition and personality of this man a few of his character traits will be revealed first as derived from the old records. He certainly was one of the more colorful persons of his time. He was in the local courts and records many times his early years as will soon be seen.

He was only 19 when he had his first brush with the law. On 22 May 1663, he was fined fifty pounds of tobacco by the local courts for breaking the Sabbath. On 16 Oct 1666, he was back in court again, this time as a plaintiff when he sued James Jolly for one half of a crop of corn and tobacco. He claimed that Jolly had been his partner in a crop jointly raising corn and tobacco. He finally settled for one fourth of the crop.

On 12 March 1667 he was convicted of fornication and he paid a fine of 500 pounds of tobacco. He was only twenty-three. In May of that same year, he was sued by a former partner who lost the suit on a technicality

In 1668 and at age 24, he settled down a bit and married Mary, the widow of James Bonewell. They bought 600 acres from Capt. John and Matilda West and soon bought an adjacent 800 acres from Richard and Mary Hinman. They lived from 1670 to 1680 in a brick home located near present day Onancock. He must have prospered because he was listed later as having 6 tithables on the tax list.

In 1669 he threatened publicly to thrash West. This was the same year he was appointed Constable for his district with Teague Anderson as his deputy. While he was serving as constable, an escaped prisoner was delivered to his custody. The prisoner promptly escaped again but was recaptured later and delivered to his master’s custody.

On 26 August 1669, while he was on jury duty, the court delivered an order for William Silverthorne to deliver a plantation to Roger. He was the plaintiff while on jury duty! He was sued or someone else sued him several times over following years.

The suits would be considered minor today. In any case he was not a stranger to the local courts having been both a plaintiff or a defendant in a number of cases. He was a juror, grand juror, church vestryman, constable and surveyor of the highways during that time. He was accused of wife beating and drunkenness. Mary had left him several times and had gone back after each separation.

She was gone from him again when he went to Jamaica. In 1680 Roger and Mary had signed legal documents to separate as man and wife. While in Jamaica he met and married the 18 year old Margaret Anderson. Then his fortunes really took a turn for the worse. After he got back to Virginia, one of his servants Patrick Michael (no kin) swore in court that he saw Michael assist in the birth of a child to his new wife. Bess, a Negro woman, also swore to the same.

Roger found himself in deep trouble then. But in the weeks following it was revealed that Patrick Michael had conspired with Bess to frame and embarrass Roger. When the truth came out by Bess admitting publicly about the conspiracy, Patrick ran away but was caught many miles distant.

Even though he was vindicated this must have had a serious effect on Michael as his debts starting piling up and he was forced to sell his land. He disappeared in early 1681 as his estate was attached for 1800 lbs. of tobacco.

But Roger was not gone from the Eastern Shore. Oh no! He re-appeared with a vengeance. He had formed a loose alliance of pirates and picaroons in the Chesapeake Bay and proceeded to carry out depredations up and down both sides of the Bay. A new Governor had taken office in Virginia and had issued various edicts that were largely ignored by the pirates. The official guard ships were mostly ineffectual because the pirates were smart enough to stay near the shore in shallow water. Their boats were small and easily navigated the small creeks and other waterways. He avoided capture by staying in the shallow waters where the larger guard ships sent after him could not go.

On Jan. 20 1685, a ship laden with twenty thousand pounds of tobacco had left port on Maryland’s Eastern Shore bound down the Chesapeake. As night fell the small ship and her crew decided to spend the night in the lee of Watts Island which was located west of upper Accomack County. This was a big mistake as Watts Island was a base of operations for Roger. The ship was instantly seized, the tobacco was stolen and the crew captured. The ship’s crew was held on the beach while Michael and rest of his men feasted on mutton and turkey with brandy and rum to top it off. Two days later the hungry prisoners were freed on a local marsh and stripped of all their clothes in payment for the hospitality received. It was January. Luckily none perished as they all made their various ways to safety.

Michael’s raids had just begun. He plundered both sides of the Bay, in Maryland and Virginia and generally caused a reign of fear amongst the citizenry. He raided settlements of Indians as well as the white colonists. Near panic had set in when finally the Governor had set in motion a concerted movement to capture Michael. He was not impressed but did move his operations to North Carolina. That was a fatal mistake.

There the Governor of North Carolina was warm and cold to the actions of the pirates. Some times he ignored their activities and then at other times he put his foot down. It was during one of these latter periods that the travails caused by Michael ceased. The Governor later reported that some pilfering pirates had been captured and the "chiefest" of them had been executed.

Roger Michael had apparently met his fate at a premature age of forty-two having had more experiences than many men twice his age.

Robert L. Mears, Author


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