Overseeing the Milwaukee Avenue Bank, Dewey ran for election to the United States House of Representatives in 1938.

After graduating from Yale in 1904, he engaged in the real estate business in Chicago, Illinois, from 1905 to 1917 served in the United States Navy from 1917 through 1919, being honorably discharged with the rank of senior lieutenant.

Mellon appointed Dewey the chairman of the Committee on Currency Design to provide recommendations to the Bureau of Engraving and Printing.

This committee is best known for its design of Federal Triangle in Washington, D.C. Dewey convinced Mellon to hire Edward H. Bennett as a consultant to the project.

[1] Dewey resigned from the Treasury on November 16, 1927, to accept an appointment as financial adviser to the Polish Government and director of the Bank of Poland, a position he held for three years.

[1] He returned to Chicago in 1931 to join Colgate-Palmolive Peet Company as vice president and chairman of the Finance Committee.

[3] In April 1948 he was appointed agent general of the Joint Committee on Foreign Economic Cooperation, a review board for the Marshall Plan, and served until June 1952.

[5] Another son, Charles, Jr., who died at age 65 in 1974, also served in World War II, with the Office of Strategic Services in China, and was awarded the Medal of Freedom.

[6] Dewey's house in North Chicago, Illinois, seized by the government in 1918, was listed on the National Register of Historic Places in 1985.