Historically, there is very little we know regarding the life of Wingina: the wereoance of the Secotan tribe of modern-day North Carolina. A wereoance was the title given to the Secotan chief, which is probably why he was the first Secotan to confront an English colonist in colonial history.
FIRST MEETINGS
The source that describes Wingina is a very reliable one, to say the least. His behavior and actions are detailed precisely by the colonists who wrote about him, primarily Englishmen Arthur Barlowe, who writes about his initial encounters in his extensive letters to his boss Walter Raleigh.
When the Tudor Era Englishmen who first met him listened to Wingina tell politically motivated stories, they were skeptical. Both Wingina and the Tudor explorers had their own distinct socio-economic interests directly correlated to whom they were serving. The Tudor Englishmen were there on behalf of their Queen Elizabeth I, who had been swayed by the famously infectious charm of Sir Walter Raleigh, and told him to find a: "remote, heathen and barbarous lands, countries and territories, not actually possessed of any Christian Prince or inhabited by Christian People."
During the 16th century, European monarchies were economically intrigued by the concept of a passage through the New World to Asia, preferably China. Unfortunately for the Europeans, there was no passage and certainly no way through North Carolina or Virginia. However, after exploring the isthmus-ridden Carolina coastline, the Spanish misconstrued the vein-like waterways as a potential strait leading them to China. Moreover, when Queen Elizabeth royally supported the expedition to the New World, she was hoping for riches and passages. Especially Sir Walter Raleigh, whose primary goal was finding the fabled El Dorado somewhere in the colonies of New Spain (also known as Mexico, Central America, and South America).
WINGINA ASKS FOR A FAVOR
During Wingina's conversation with the English colonists, he told them about
a rival tribe called the Neiosioke, who he claims committed a duplicitous attack on the Secotan. According to Wingina, after years of fighting, the two warring tribes--Wingina's Secotans and the Neiosioke--decided to conduct a feast with the Neiosioke "king" and discuss a peace agreement. However, during the friendly feast, the Neiosioke launched a surprise attack on the Secotans. When the dust settled from the subsequent battle, Wingina found that all his men were slaughtered.
Wingina requested the two leading English explorers, the aforementioned Arthur Barlowe and Philip Amadas, to assist him in a retaliating surprise attack on the treacherous Neiosioke. Barlowe, who is our primary historical source on Wingina, declined the indigenous king's violent favor. Barlowe was not sure: "whether their perswasion be to the ende they may be revenged of their enemies, or for the love they beare to us," and eventually decided to pursue a neutral position with the Secotan instead. After Raleigh read their reports, he immediately began seeking funds to start a colony on Roanoke.
Meanwhile, Wingina was already not too keen on the Englishmen who had rejected his military proposal. In contrast, Wingina's brother, Granganimeo, had liked the Englishmen and would go on to be their most potent political ally upon their return from England.
THE BEGINNING OF ROANOKE COLONY
Despite his pleas for a military alliance being denied, Wingina was relatively welcoming to the English colonists. Once Sir Walter Raleigh obtained funding, he began sending colonists to the isthmus to settle the land. And due to Wingina being the chieftain, the English desired a peaceful relationship with him. (Though the English referred to him as a king due to their European-fueled frame of reference).
Ironically, Raleigh never even set foot in his Carolina colony. Instead, the hands-on leadership of Roanoke was given to Ralph Lane. Lane's official title was Governor of Roanoke. His governorship began in 1585 but would only last one year after months of misfortune that started with the initial voyage.
While on their way to Roanoke, a ship in Raleigh's fleet, known as the Tiger, hit a shoal, causing a leak in the storage compartments where the most essential supplies were kept. Put another way, the food on the ship was soiled. This unfortunate accident meant the over 100 colonists on Roanoke would have to rely on Native American aid.
Wingina, of course, had no idea that the colonists he had met previously were in dire need of his tribe's food upon their arrival. His brother Granganimeo, however, was more than willing to provide food and other supplies to the desperate English colonists. In fact, Granganimeo acted as their most enthusiastic supporter throughout his brief relationship with the English, always advocating on their behalf during tribal council meetings, often going against his brother Wingina, who was always wary of their new neighbors. If not for Granganimeo and other pro-English Secotan People, the Roanoke colonists would have struggled to survive on the little supplies they salvaged from the Tiger.
However, for what they lacked in food and supplies, they made up for in curiosity and viral diseases.
When Lane and his associates landed, they almost immediately began exploring the land around Roanoke, hoping to study Secotan society and perhaps find either gold or a strait to Asia. They only saw the former. Moreover, when they did conduct communication with Wingina and his fellow Secotans, the colonists inadvertently gave their patrons smallpox, including Wingina himself.
THE PRAYER
Scholars are not sure precisely which illness Wingina and his subsidiaries suffered from, but whether it was smallpox or influenza, Wingina became gravely ill. He initially consulted Secotan healers, but when they failed to heal him using their methods, he reached out to the English, whom the Secotan believed had brought this seemingly supernatural plague and were, therefore, its primary catalyst. Under those partially correct presumptions, Wingina asked for alleviation from his illness. The English---who were more than willing to seize the opportunity to further cultivate their relationship with the Secotans---happily obliged and uttered prayers for Wingina.
Ostensibly, the prayers were effective. Wingina recovered and credited the English's power with saving him, so much so that the Secotan chieftain further requested the English help to pray away the other Secotan People's "supernatural" illnesses. However, this positive sentiment would not last long.
THE BRIEF REIGN OF PEMISAPAN
After Wingina's brother Granganimeo died, the chieftain changed his name to a far more hostile one: Pemisapan. In the variation of Algonquin that Pemisapan spoke, his new name meant "One Who Watches," implying a new adversarial approach by the Secotan People in their already fragile relations with the Roanoke colonists.
With their most influential ally dead, the English began to see Pemisapan as a serious threat. Ralph Lane realized Pemisapan could be a potential enemy to their cause, which was to establish a colony at Roanoke, given his current name change and generally hostile attitude towards his English subsidiaries. Nevertheless, Lane's skepticism did not impede him from seeking out Pemisapan for valuable information.
Lane sought Pemisapan out to help the governor map out a plan for exploration beyond Secotan-occupied land. Pemisapan, on the other hand, saw an opportunity to hurt two of his enemies: the English colonists and the Chowanoke, another tribe located west of Secotan land. When Ralph Lane met with Pemisapan, the latter spun the former a clever lie. Pemisapan warned Lane that the Chowanoke and their chieftain Menatonon were planning an attack on Roanoke. Subsequently, Pemisapan warned Menatonon that the English colonists would be arriving soon with violent intentions, which now they were due to Pemisapan's duplicitous schemes.
However, the English's attack was so successful that they could kidnap Menatonon and hold him for ransom at Roanoke, where the chieftain revealed valuable information on metal-rich lands ruled by a mighty king. (Historians theorize Menatonon was idyllically referring to Powhatan in Virginia). Pemisapan's plan had backfired. Now, the English colonists were preparing to explore more of the New World, Pemisapan's world.
Though he continued to withhold support from the colonists, Pemisapan eventually succumbed to the trend of propagating English interests after powerful tribal leader Oksiko swore loyalty to Queen Elizabeth I, leading to the balance of power to tip in Roanoke's favor.
Despite most tribal leaders being pro-English, Pemisapan still managed to procure an inner circle comprised of anti-English leaders, except for one chief, Ensenore. Ensenore served as an advocate for the English amongst anti-English tribal leaders. And upon his death, the Roanoke colonists--who were quite familiar with the political movements of their indigenous neighbors--knew there was no longer an advocating voice inhibiting Pemisapan from attacking Roanoke.
Ensenore's son subsequently Skiko inherited the chiefdom. Skiko, at least according to the perceptions of Pemisapan, was, in contrast to his father, anti-English. This trusting sentiment led Pemisapan to begin forming a war council amongst his largely anti-English inner-circle with Skikio involved, despite the new chief currently being held for ransom at Roanoke.
Pemisapan eventually scheduled his war council to prepare for an attack on Roanoke. In other words, all of Roanoke's enemies would be together in one place for a lengthy period. It was the perfect opportunity for Skiko to return to his captors and honor his father's pro-English stance by telling the English colonists precisely where and when the council would take place.
Using the information provided by Skiko, the English ambushed Pemisapan'a war council. Many shots were fired, but Pemisapan, limping from a bullet wound, escaped into the forest. Given his injury, however, Pemisapan could not travel swiftly enough to get away safely. A colonist, Edward Nugent, tracked Pemsiapan down and returned to Roanoke with the chief's severed head, where it was proudly displayed outside the colony's fort as if to celebrate the defeat of a dangerous enemy.