[8] At Henry Phipps' death, his father, who was at one time the second largest shareholder of Carnegie Steel and was a founder of Bessemer Trust, was worth $3,121,810 (equivalent to $56,939,000 in 2023), according to transfer tax appraisal documents.

They became a major owner and breeder in Thoroughbred racing with numerous champions including 1957 American Horse of the Year Bold Ruler who went on to be an eight-time Leading sire in North America and whose progeny included the legendary Secretariat.

[11] In December 1907, Phipps married Gladys Livingston Mills (1883–1970)[12] at her parents' home in Staatsburg, New York.

[13] Gladys was the daughter of famed financier Ogden Mills and the twin sister of Beatrice, who married Bernard Forbes, 8th Earl of Granard.

[15] As a wedding present, her father bought them a marble‐fronted townhouse at East 85th Street and Fifth Avenue.