Elizabeth Shirland was born around 1577 in Devonshire, England. Elizabeth and some of her family joined a group of settlers to live on a colony founded by Sir Walter Raleigh in 1585. Elizabeth was known as a very beautiful yet vigorous and energetic girl, and maybe that is the reason for her career after the mysterious happenings on Roanoke Island. Some chapters of Elizabeth Shirland's life are suspected to be fictional, especially when it comes to the mystery of her lost booty. Hidden treasures always inspired the fantasies of story tellers who passed on the legends of secret wealths.
Although John Cabot (ca. 1450-1499) established an English claim to the North American continent as early as 1497-1498, more than half a century elapsed before Englishmen turned their attention to the new lands. The most well-known early colony was founded by Sir Walter Raleigh (ca. 1554-1618) on Roanoke Island, off the coast of present-day North Carolina. In 1585, Raleigh's men settled on the small island. Raleigh sent groups of settlers for three years, beginning in 1584. (Raleigh's initiative was successfully imitated by a group of London investors who founded Virginia in 1607.) Relations with the Native American inhabitants were peaceful at first, but as the colonists' supplies dwindled, amity dwindled too. The colonists left in 1586 after beheading the local Indian chief, Wingina.
Raleigh arranged for Governor John White and a group of families to return to live in peace with the natives in 1587. Violence, however, is not easily forgotten. Within one month, hostilities resumed, and White was forced to return to England to ask Raleigh for reinforcements. Time was not on White's side. When the war with Spain erupted, White could not return to the colony for three years. When he set foot on Roanoke Island in August 1590, he searched frantically for the settlers, including his daughter and granddaughter, the first English New World baby, named Virginia Dare.
All that could be found was the remains of a village and a mysterious word, "CROATOAN," engraved on a tree. White concluded there must be a connection between the word and a nearby Indian tribe, but before he could investigate, a violent storm forced him out to sea and back to England.
Left for three years, the 117 men, women, and children had disappeared mysteriously. This lost colony remains one of the greatest mysteries of the colonial period. Although Raleigh sent an expedition to search for them, the colonists are never found and their fate remains unknown.
However, it is known that Elizabeth Shirland was amongst those settlers. It is rumored that after being left behind the colonists built a wall around their homes for protection from the Indians. This was the wall that John White found on his return to Roanoke Island in 1590. The men would leave the fort to hunt and fish as the colonist's food supply eventually ran out. The Indians ambushed and killed each man as they left the fort. In time all the men were killed and the Indians captured the women and children. The Indians took the hostages to their villages to live and work as slaves.
Elizabeth was raised by Indians and left the island 1589 on board of a Spanish ship after she was picked up by Spanish soldiers. It is said that she was held captive and raped several times by the soldiers before she killed her sentinel with his own knife during the turmoil of a pirate attack a few weeks later.
Disguised as a young man she had served under the command of Sir Francis Drake, before she returned to England and got married in 1595. However, she could not stand the life of a housewife and soon left her husband and went to sea again. Little is known about her life and destiny from that point forward. She returned to York, England again once or twice, where she gave birth to a little son. Soon afterwards she left her family for good.
Elizabeth had prepared her own career as a woman pirate. It is safe to assume that she was inspired by the criminal career of the famous woman pirate Grace O'Malley. When she was captain on her own ship, she disclosed her sex to her crew and she commanded and ruled them with her iron will and her strong ability to assert herself. She used men from the crew for her sexual pleasure, and some of them left the ship with a cut throat. Due to that fact and her ability to master the blade she was also known as the Cutlass Liz.
Cutlass Liz was not too successful as a pirate captain, and hardly anything is known about her operations. The only successful strike reported was the capturing of a Spanish merchant in 1604, where Cutlass Liz looted silk and gold before burning the captured ship. A few weeks afterwards she was betrayed to the Spanish by two members of her crew and was arrested while making love to one of her traitors. As the Spaniards dragged the naked woman pirate from the bed, she was suddenly aware of the treason and managed to stab her lover with the dagger she had hidden beneath her pillows. She was instantly killed by the soldiers, what spared her from public humiliation and the painful death of hanging.
However, her only mentionable booty - gold and goods worth at least £ 30,000 - was not on board of her ship anymore and could never be retrieved.