Born in Manorville, New York, Raynor studied civil engineering at Princeton University. He left school without graduating in 1898 and began his career working as a surveyor. In 1908 he was hired by Charles Blair Macdonald to survey the grounds and supervise construction for the future National Golf Links of America, which was completed in 1911 in Southhampton, New York. This commission began a long professional relationship with Macdonald, under whose tutelage Raynor built numerous golf courses, including those at Sleepy Hollow, Cleveland, Ohio; Piping Rock, Locust Valley, New York; and the St. Louis Golf Course, Missouri. When Macdonald retired in 1914, Raynor began his own practice and assumed Macdonald’s clients. Raynor’s designs continued in the same vein as Macdonald’s work, incorporating many motifs that figured consistently in his predecessor’s projects, such as a “Punchbowl” green. Raynor fitted these obstacles into the natural landscape, but was not averse to significant earth-moving and manipulation if the result was still a natural-looking green. His signature element was to create a deceptive fairway, giving it a sense of length that it really lacked. Raynor designed over 50 courses across the country in his brief career, including Fishers Island, New York; Mountain Lake, Lake Wales, Florida; and Shoreacres, Lake Bluff, Illinois. He died in the prime of his career, at the age of 51.