[2][3] His father served as bookkeeper, then secretary-treasurer of the Chicago Tribune, and worked closely with owner Joseph Medill.
[1] During his senior year, Cowles was captain of the Yale champion varsity crew which set an upstream record on the Thames River which remained unbroken until 1923.
[citation needed] Over the years, Cowles continued to be involved with the Yale crew, serving as chief advisor to head coach Edson F. Gallaudet in 1899.
[1] A campaigner against government waste, he served as president of the Civic Federation and the Bureau of Public Efficiency from 1932 to 1935.
[1] He had heart disease and died from pneumonia at his home at 1130 Lake Shore Drive, Chicago, on January 15, 1939.