Harley Wilfred Jefferson was born in Danville, Pittsylvania County, Virginia on 18 October 1883. He started his tobacco career in his father's business W.T. Jefferson & Company in Danville, Virginia. Working behind an auctioner buying and selling tobacco at the age of 16. He then worked as a purchaser and wholesaler for his father traveling from around Virginia to North and South Carolina. It is guessed that is how he met his wife Leila Alma Shannon from Henderson, North Carolina. They were married in Vance, North Carolina, 16 June 1909. In 1901 Harley, moves with his parents to Wisconsin. Like his father, he works for the American Tobacco Company, Leaf Division making $1.50 a day. He leaves the company in 1908, joining his father in the newly organized, Jefferson Leaf and Tobacco Company in Sparta, Wisconsin working as the company's Secretary and Treassurer. Here he worked with his father, William Tazewell Jefferson, his Uncle Kelly Bennett Jefferson and his brothers in the family business. He is the founder of "Polly Falls" the family cottage. Harley purchased it from a lumber company in 1916 with the thought of making it into a family gathering place. That it became and remains so to this day. He named the place Harelton Lodge but that name never took. Polly Falls it remained. Generations of family have met there ever since. His wife Leila dies in Sparta, Wisconsin in December of 1922 and a short time later, he moves to New York City taking a position with the P. Lorillard Company. In 1925 he becomes Assistant Manager of the Leaf Division in New York City and works his way to Vice-President of P. Lorillard. Katherine Wise and he marry in New York in 1926. She is a long time friend. She and her sister, Megs, were constant visitors of "Polly Falls". During the World War II years, 1942 to 1945, he was Chief of the Tobacco Section of the War Production Board. He looses his only remaining son, Harley W. Jr, "Bud" in a plane crash in 1943. That fact coupled with the fact that he and Katherine are living on the east coast and she did not particularly like the outdoors, he sells Polly Falls. His sister Sallie Virginia and her husband, Arthur Chester Brigham, his nephew, William Hinton "Bill" Jefferson and Bill's uncle, George W. Hinton purchase the property in 1951. In 1946 he is asked to run Waitt and Bond Inc. He resigns that position in 1956 at the age of 72, but he remained with the company as a director and consultant until his death in 1958. His remaining years are spent on the east coast. President Dwight D. "Ike" Eisenhower was a golfing buddy. Ike even came to Sparta and stayed at Polly Falls and then played a round of golf at the course his father W.T. and Stuart McGriffin had started in 1915. Harley was also a close friend with then popular singer Kate Smith as well.

He died in East Orange, New Jersey in 1958. He is buried in the Jefferson Family plot, Woodlawn Cemetery in Sparta, Wisconsin.