Clipper Wilkinson is a hunter and surveyor from Virginia. Actually, surveying and hunting are the family business. His father and brother are surveyors (and crack shots) as well - making the market in his small hometown somewhat oversaturated. Hell, making market in his HOUSE somewhat oversaturated.
Wilkinson moved to New York looking for work - unfortunately arriving just in time for the opening events of the Revolution. He remained neutral for the first part of the war, but after seeing the cruelty of the Redcoats' actions in Boston, he started leaning toward the rebel side - putting himself at odds with the rest of his family, who are Loyalists.
It seems Connor has a talent for attracting friends with family troubles.