Dale may have been a member of the Dale family of Surrey County, England, or of an Anglo-Dutch family. No known documents record the date and place of his birth, the names of his parents, or any details about his education. He wrote equally well in English and Dutch, was probably fluent in French, knew at least some Latin, and was a deeply committed Protestant. Dale stated late in 1617 that he had begun his lifelong career in the military as a common soldier in the service of the States General of the Netherlands about thirty years earlier, at which time England and the Netherlands were at war with Spain. By 1594 he was a captain in the English army. Dale may have volunteered without a commission to fight against the Spanish, as young gentlemen seldom served in the ranks, and men from the laboring and yeoman classes seldom became officers. He may also have made a socially and financially advantageous first marriage about which nothing is now known.
In 1598 and 1599 Dale commanded an English company in Ireland under Robert Devereux, second earl of Essex, and was briefly detained two years later after the earl was charged with treason. Dale was personally known to Henry IV, the king of France, on whose recommendation the States General appointed him captain of a Dutch infantry company in August 1603. England’s James I knighted him on June 19, 1606. Dale was evidently close to King James’s young son and heir, Prince Henry, who early in 1611 requested that the States General grant Dale a three-year leave of absence without pay to serve in Virginia. Dale married Elizabeth Throckmorton before he departed for Virginia in the spring of 1611; they are not known to have had any children.
The Virginia Company of London, in which Dale owned shares, appointed him the colony’s marshal, or the army officer in charge of discipline and order. The company also designated him deputy, or acting, governor in the event that both the governor, Thomas West, baron De La Warr, and the lieutenant governor, Sir Thomas Gates, were absent from Virginia. Dale and about 300 well-armed soldiers reached the colony in May 1611. He immediately issued orders to erect palisades at the James River settlements to secure them from attack. With De La Warr and Gates both out of the colony, Dale was acting governor until Gates returned in August 1611. Dale was a member of the governor’s Council after March 1612 and was acting governor again from March 1614 to April 1616.
On June 22, 1611, Dale issued military regulations under which his soldiers were to act while in Virginia. They supplemented civil orders that De La Warr and Gates had promulgated in 1610 at the company’s direction. In 1612 the combined orders were printed in London with the title For The Colony in Virginea Britannia. Lawes Divine, Morall and Martiall, &c. The civil orders prescribed severe corporal punishment or death for many infractions, as did Dale’s military code. Although sharply criticized for governing Virginia by brutal martial law, Dale did not hesitate to impose the severe penalties specified by the codes, including forced labor, capital punishment, and condemning a man who stole food to be tied to a tree and left to starve to death as a warning to others. The civilian and military regulations, harsh as they were, were not notably more severe than the orders that other English officers imposed in Ireland and elsewhere, and by the standards of the time the soldiers and many of the residents of Virginia were not all entitled to the protections of the common law.
Dale’s imposition of discipline and his directions for organizing necessary work converted the fractious, inefficient colony into a reasonably well-run military and commercial outpost. As soon as he arrived, Dale ordered men to sow grain and tend the large stock of cattle and swine that the company had sent to Virginia. In June 1611 he attacked and defeated the Nansemond Indians and burned their towns. Later in the summer he marched against Indians farther up the James River and established a settlement on a bluff that he called the City of Henrico, or Henricus, in honor of his patron Prince Henry. In December, Dale attacked the Appamattuck towns in that vicinity and later founded on their land the settlement known as Bermuda Hundred. After Samuel Argall, later deputy governor of Virginia, captured Pocahontas early in 1613, Dale held her as a guarantee of peace with her father, Powhatan. Dale and Alexander Whitaker, the minister at Jamestown and Henricus, directed her conversion to Christianity, and in 1614 Dale assented to her marriage to John Rolfe.
The first professional military man in Virginia to command a large and properly equipped force, Dale succeeded where previous commanders had failed and earned commendations from company officers, the king, and some of the surviving colonists. His campaigns against the Indians were the concluding actions in the First Anglo-Powhatan War and allowed the colonists to live in comparative peace for nearly a decade. Dale fended off a Spanish incursion into Virginia and reportedly threatened to hang some French Jesuits who, en route to New France, were driven into Virginia during a storm. His stern enforcement of discipline and careful husbandry of the colony’s livestock and other resources helped make Virginia largely self-sufficient within five years and marked the end of the repeated failings that had plagued the colony’s founding. Dale sent samples of iron to England, established a fishing settlement and saltworks on the Eastern Shore at a site called Dale’s Gift, and acquired property near Henricus.
When his three-year leave of absence expired in 1614, Dale was more than ready to leave Virginia and resume command of his Dutch company, but he stayed on, and the king himself requested that the States General extend his leave of absence. Dale finally left Virginia with John Rolfe and Pocahontas in the spring of 1616, having had primary responsibility for the colony’s military affairs and a major role in its governance for more than half of its nine-year history. He returned to England with a cargo showing what the colony could produce: pitch, potash, sassafras, sturgeon (and caviar), and tobacco, among other commodities. The cargo and the condition of the colony presented vivid contrasts to Virginia’s desperate straits at the time that the company had recruited Dale to take charge of its defenses. Safely home in England, he boasted that he had “returned from the hardest taske that ever I undertooke & by the blessing of god have wth poor means left the Collonye in great prosperitye & peace contrarye to many men’s expectation.”
Late in 1617 Dale petitioned the States General for full pay for the whole time of his absence, which with the assistance of the English ambassador he received. Rather than resume his career in the Netherlands, he took command of another large-scale and important enterprise, an English force that the East India Company sent to the Indian Ocean to counter the commercial influence of the Dutch East India Company. Dale wrote a short will on February 20, 1618, leaving to his wife his estates in England and Virginia, which his widow still owned at the time of her death in 1640. En route to India, Dale almost drowned in an accident at Penguin Island, off the coast of modern-day Namibia. In December 1618 he engaged Dutch forces in heavy fighting off the coast of Java, where he occupied Dutch trading posts. The following summer Dale sailed to Machilipatnam, or Masulipatam, on the east coast of India, where he became ill and died on August 9, 1619. He was buried there in a tomb erected for the purpose.