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Why did the Roanoke leader Wingina favor establishing a relationship with the English?

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Hi Seemi;
Great question!  Thank you for this opportunity.
 
My background is in anthropology.  I study stone-age cultures unaffected by Western civilization.  This would include a concentration on cultures located in Western United States.  I never heard of this character until now.  I therefore researched such on Wikipedia.  He is from North Carolina and lived in the 16th century.  Henceforth, all records are from English explorers and settlers of this time.  It may or may not be accurate.
 
It is my understanding from Wikipedia, that Wingina needed this alliance with the English to assist with a conflict against another Native culture of this region.  In my opinion, this makes sense, especially since the settlers had more advanced technologies.
 
Furthermore, to go beyond your question, the article on Wikipedia is working on the premise that Wingina was male.  In many cultures all over the world, leadership is often female.
 
For example, the !Kung of South Africa, as well as the Agta of the Phillippines have both male and female leaders.  And such women are just as feminine as their non-leadership, female counterparts.  However, there is only culture, to my knowledge, in which women are warriors.  These are the Dahomeans.  Such women try to be masculine.
 
In the Wikipedia article, I find no reason to believe that Wingina was a warrior.  Henceforth, this individual may have been a female.
 
If you do more research, and learn perhaps that Wingina was a hunter, then this individual may still be female.  The Agta are one example of a culture in which women hunt.  However, worldwide, females are never known to participate in large game hunting.  The !Kung hunt giraffees, among other large animals.  In such culture, the task of hunting is monopoloized by men, while they share leadership statuses with women.
 
I looked at the list of sources in the Wikipedia article.  These are all 20th and 21st century publications which cite the notes of the original English explorers of the region.  This is extremely unreliable, especially since these authors are likely working on the premises that men hunt and lead.  If you can access copies of the original notes, that would be a better resource.  And if you can find a descendant of the culture to which Wingina belonged, the Secotans, that would be best.
 
Otherwise, these are two books I love,
NORTH AMERICAN INDIANS, by Bill Yenne
WOMAN THE GATHERER, Estioko-Griffin & Griffin, editors
 
In the latter book, you will find the information on the Agta and !Kung.
 
I hope I was helpful.  I wish I could do more.  Please let me know if there is anything else I can help you with.