[1] Chatfield-Taylor began his business career in 1916 with the Central Trust Company of Illinois (which had been formed in 1901 by former Comptroller of the Currency Charles G. Dawes before he became Vice President of the United States under Calvin Coolidge).

Later, he worked for Field, Glore, Ward & Co., an investment banking house in Chicago, becoming vice president of the business in 1927.

He was also vice president of the Chicago Investors corporation and a director of the People's Trust and Savings Bank.

[9][10] He resigned in February 1939 over differences over Treasury policies with Secretary Morgenthau to become the European delegate of the American Red Cross.

[14] In 1944, he was the federal official who took charge of Montgomery Ward & Co.'s Chicago plant after it was ordered seized by the government and the firm's chairman, Sewell Avery, was removed from the premises by soldiers.

His widow died on August 31, 1977, in Greenwich, Connecticut and was buried at Hollywood Cemetery in Richmond, Virginia.