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This box primarily consists of legal documents from a variety of O'Donnell's labor cases and other legal matters, primarily concerning the Irish community, that he was involved with during the 1930s and early 1940s, such as the consolidation of the Donegal Association, Inc. The box also contains minutes from 1966 and 1967 meetings of the Columbia University Seminar on Labor, which O'Donnell presided over as chair.

About half of the materials in this box are correspondence and legal documents related to O'Donnell's work on behalf of the Transport Workers Union of America (TWU) during the 1970s through the 1990s, including a few folders pertaining to specific locals. His work with several other unions is also documented, though to a much lesser extent.

The other half of the box contains information on O'Donnell's family history and biographical information on O'Donnell's early life and education, compiled by Eileen Ginn for her biography of O'Donnell. Ginn's correspondence and notes written in the course of conducting her research are also included. O'Donnell gave numerous speeches, often in the form of radio broadcasts, on Irish Republicanism and other topics, and transcripts and notes he made in preparation for his speeches are also present.

This box mainly pertains to O'Donnell's legal advocacy for the TWU and the American Postal Workers Union in the 1980s and 1990s. The TWU materials relate mostly to specific locals and the TWU's collective bargaining agreement with the New York City Transit Authority and the Manhattan and Bronx Surface Transit Operating Authority. TWU constitutions from the 1940s to 1980s are also present. Additionally, there is a small amount of material related to the Utility Workers Union of America and the Communications Workers of America, as well as court transcripts of the 1951 open hearings before the Mayor's Special Transit Committee on the transition to a forty-hour work week.

A 1936 letter from Irish Republican Army leader George Gilmore to O'Donnell, along with a typed transcription (likely created by Ginn), is also included.

This box contains O'Donnell's copies of the Manhattan and Bronx Surface Transit Operating Authority's "Exhibits for Contract Negotiations" from 1967, 1969, and 1976; the New York City Transit Authority's "Exhibits for Contract Negotiations" from 1959, 1961, 1963, 1969, 1971, 1976, 1978, and 1980; and the New York City Transit Authority's "Economic Fact Book" from 1967 and 1969. Also included in this box are countless other copies of various reports, collective bargaining agreements, and constitutions and by-laws concerning or produced by the American Postal Workers Union, the Utility Workers Union of America, and other unions.

This box contains recordings of oral histories that Eileen Ginn conducted with O'Donnell and those who knew him as part of her research for her biography of O'Donnell. The recordings are on DVDs, CDs, and cassette and microcassette tapes. Transcripts of some of the interviews are also included.

This box contains photographs of O'Donnell, mainly giving speeches or making presentations on behalf of the TWU.