Oscar F. Cooke was born in Salt Lake City, Utah, in 1869, the son of Herman and Matilda Cooke. He came to Portland from San Francisco with his parents, at the age of 7, but the family relocated to a land claim in Idaho and later settled near Fort Walla Walla. One of Cooke’s brothers, Hermon, became a lawyer, settling first in Tenopah, Nevada, and later in Reno. Another brother, James Daniel ("Dan") Cooke, was a farmer near Hillsdale, Oregon. Oscar Cooke returned to Portland in 1896 and started a general store at Sylvan. He became part owner of the Sylvan Brick Company, and later was a building contractor, farmer, and owner of numerous rental properties. He owned property throughout Multnomah and Washington Counties in Oregon, as well as in the City of Portland and southern Washington State. He began the West Hills Winery in the late 1930s and ran the enterprise until the early 1950s. He died in Portland in 1955.

Cooke was married in 1901 to Ella Marie Gateley (1877-1957), daughter of John Gateley (an Oregon pioneer of 1859), but the couple had no children. Ella’s sister, Mary Gateley Lepper (d. 1947), married John Lepper (d. 1915), and their daughter, Helen Lepper, married Clarence Lovin, who worked for a time for the Oregon Shipbuilding Corporation.

After the death of Oscar and Ella Cooke, Ella’s niece, Helen Lepper Lovin, served as the executrix of the estate with the assistance of Portland attorney John Woerndle. There were many legal issues involved, including a conflict with John Vermillion, who had worked for the Cookes in the winery and who claimed to have been promised a portion of their legacy. Due to this and other problems, the estate was not settled until the mid 1960s.