Although John Blackwell Cobb, President of the American Tobacco Company resided in New York, he enjoyed hunting in the Jamestown, NC area and purchased 44,000 acres located between Greensboro and High Point. He eventually had a grand manor house / hunting lodge constructed near Jamestown, which was able to seat 1000 people in the ball room. He would bring friends to Jamestown in private rail cars and then arrange for horse drawn carriages to take his guests to the manor for the hunt. Cobb named the surrounding area “Sedgefield”.

In the early 1920’s, the focus of downtown Greensboro was the recently constructed Jefferson Standard Building. During those years there was a significant real estate boom which saw the rapid expansion of Greensboro’s suburbs. New names were added to the City and County maps as builders concentrated on nearby areas for development. Pilot Life Insurance expanded during these pre-depression boom years and spearheaded the trend of moving offices out to main suburban roads.

Pilot Life and Sedgefield were linked from the start. A. W. McAlister, President of Pilot Life was head of the Sedgefield Development Company – Sedgefield, Inc. Their original plan was to build another Pinehurst, a place for the wealthy to stop while travelling to their winter residences in Florida. In 1925 they built a grand resort hotel, a beautiful but challenging Donald Ross designed golf course, tennis courts and an attractive horse show arena. Polo grounds were planned in addition to a sprawling business district on the opposite side of High Point Road.

Contemporaneous with the development of Sedgefield, Pilot was establishing its nearby High Point Road headquarters, a Georgian Revival complex styled after Tryon Palace in New Bern, NC . The idea was that people would live in the Sedgefield area, work across the street in the Pilot business district and enjoy the country club and adjacent amenities.

Unfortunately, the Depression occurred and the development company filed for Bankruptcy. Pilot purchased most of the remaining property, but a planned second golf course was never built (the framed design is located in the current club house).

Many years later, after merging with Jefferson Standard, Pilot moved to downtown Greensboro and the High Point Road buildings and property remain vacant to this day.

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