Orlando Hand Bears was a Sag Harbor, Long Island native and one of several artists who attempted to capitalize on the prosperity of eastern Long Island and coastal Connecticut in the first half of the nineteenth century, generated by the burgeoning whaling industry. Bears was possibly taught by another Sag Harbor painter and distant relative, Hubbard Fordham. Ship captains, merchants and their families were Bears' subjects. Bears' career as an artist was short-lived and in 1850, the year before his death at the age of 40, he was listed in the 1850 census as a tinner. He died at the young age of 40 in Sag Harbor.