The Ashley W. Cole Letters consists of letters from friends, acquaintances, and business associates in connection with Cole's positions of newspaperman, railroad commissioner, executive secretary to New York State Governor Levi P. Morton, and London representative for a manufacturing firm.

As railroad commissioner, appointed by Governor Morton and later retained by Theodore Roosevelt, Cole received correspondence concerning commission reports (Robert Avery), requests for hearings (Avery Andrews, Paul D. Cravath), speaking invitations (Chauncey Depew, James Jerome Hill, Jeremiah Jenks), and offers of assistance (Frank Julian Sprague). Perhaps the most interesting letter among those pertaining to his association with the Railroad Commission is an item to Theodore Roosevelt asking if the President had referred to that agency as "the most worthless of all the State bureaus." In an answer from secretary George Cortelyou, Roosevelt denies both the opinion and the statement.

There is a considerable amount of correspondence from actress Louse D. (Mrs. Leslie) Carter in which she appeals to Cole for money, and to intervene with the New York newspapers on her behalf, as she felt she was being treated unfairly by them. Other letters relating to Mrs. Carter are from William Brookfield and Dr. Oscar King.

There are also a number of letters from sculptor Jonathan Scott Hartley concerning the commission for the John Ericsson monument in New York City. The letters recount the execution of the project from the awarding of the commission through the unveiling ceremony for the finished sculpture. Hartley's letters also mention his father-in-law, painter George Inness.

The correspondence contains a number of letters from Thomas Collier Platt in which he discusses his successes and defeats in various political campaigns. In addition there is a substantive letter from L. Bradford Prince in which he reminisces about his public career in New York and the political situation in Mexico, to which territory he had been appointed to serve by President Rutherford B. Hayes (15 Nov 1901): "My only mistake was in coming away, when the glamour of historic interest enticed me finally to accept as Chief Justice, after I had declined the Governorship of Idaho and 4 other places."

The remainder of the correspondence centers around arrangements for meetings (A.J. Dittenhoefer, A.H. Green, Thomas Lemuel James, Victoria Woodhull) and recommendations for appointments (Amos J. Cummings, Frank Hatton). There are two personal letters from Robert J. Wynne, and an appeal from poet Ella Wheeler Wilcox to intercede for release of a prisoner whom she believes was unfairly prosecuted because of his interest in the occult sciences.