The bulk of the correspondence is between Osborn and his wife shortly after their marriage in 1894. Items of interest include mention of business talks with industrialist James B. Duke and a description of a conversation arising from the integration of a train car.
Business and political correspondence includes letters from Secretary of Treasury William G. McAdoo, President Woodrow Wilson, Secretary of the Navy Josephus Daniels, Comptroller of Currency John Skelton Williams, and others connected with Mr. Osborn's tenure of office. Letters from McAdoo concern support expected from President Wilson in a forthcoming campaign while others touch upon the problems of corporate tax collection. Osborn's resignation and reaction from McAdoo and the President (1917) are included.
Newspapers and other clippings concern Mr. Osborn's career in government, and the Wilson administration. A significant quantity of material concerns Mr. Osborn's role in the investigation of tax scandals involving the oleomargarine, whiskey, and tobacco industries.
Of particular interest is Mr. Osborn's diary for 1914, written while he was commissioner of internal revenue. The diary is rich in descriptions of contact with personages of the early Wilson administration, especially those concerned with Mr. Osborn's office, such as Secretary of the Treasury William G. McAdoo. The references to Wilson, though partisan, offer many insights into Wilson and his first term. Examples of entries include criticism of Secretary of State William Jennings Bryan's alleged love of money and paid lecture tours, Comptroller of Currency John Skelton Williams's extravagantly furnished offices and his presumed control over McAdoo, and complaints of Democrats over Wilson's refusal to oust Republican employees and his appointment of Roman Catholics to office.
Many entries concern the problem of patronage, as Osborn had considerable trouble with Congress and Treasury employees. He complained continually about the inefficiency and waste caused by "spoils" adherents controlling government employment. His comments on government workers and the problems within his own administrative capacity are numerous.
Comments concerning the then current problems of the Democratic Party are rather enlightening. Tammany, payment to Panama, the lengthy session of Congress hampering Democratic campaigning, and Wilson's tendency to regard bearers of unpleasant news as disloyal are included. Congressmen from North Carolina and other states are mentioned in the diary as are Wilson administrative figures.
Miscellaneous items include a portrait of Osborn's father; photographs of Osborn as a member of an unidentified N.C. political group, W. W. Fuller, Osborn at Fuller's home, and Col. W. H. Osborn at his desk in Washington, D.C.; a report of Internal Revenue activities during his term of office; a family genealogy; a slate of Democratic candidates for the Greensboro, N.C., elections in 1901; a bill for repair of Osborn's summer home; and a copy of his tax return in 1917. This return was reportedly the first to be examined under the new income tax law of that year. Invitations, including three to the White House, reflect Osborn's attendance as an official at Washington social functions. Also included are a circular advertising Keeley Institute; a resolution of appreciation for Osborn's four years as mayor of Greensboro; a leather-bound booklet presented to Osborn on his retirement from the I.R.S. in 1917; a pamphlet entitled
Internal Revenue, Brief History of Laws Relating Thereto; and a bound volume
To Increase the Revenue, Hearings and Briefs Senate Finance Committee. Minutes (1914-1917) taken by Mrs. Osborn as secretary of the Florence Crittenton Branch of the Sunshine and Community Society of Washington, D. C., are also included. These minutes discuss cost of items given to the Florence Crittenton Home, numbers of women and babies in the home, methods of raising funds, purpose of the home, and lists of members of the society. On the reverse side of the November 1915 minutes is detailed printed information about cattle production on a Cheyenne Indian reservation in Lame Deer, Montana.