The bulk of the collection consists of an oversize scrapbook of newspaper clippings (and two oversize folders containing additional loose scrapbook pages of newspaper clippings) documenting Pillsbury's campaign for the Republican gubernatorial nomination in 1966. There are news stories reporting Pillsbury's announcement of his candidacy, editorials, articles about Republican county and district conventions and endorsements, and stories reporting on Pillsbury's campaign appearances throughout Minnesota. There are articles about the campaigns of fellow Republican contenders Harold LeVander and William B. Randall; efforts to bring former Republican governor Elmer L. Andersen into the race; the campaigns of Democratic contenders Governor Karl F. Rolvaag and Lieutenant Governor A. M. ("Sandy") Keith; and the state Republican and Democratic conventions in June 1966. There are columns and analysis pieces, and discussion about the candidates' positions on such issues as tax reform, legislative reapportionment, highway construction, the possible introduction of a sales tax, a Rolvaag proposal to abolish the office of Lieutenant Governor, and campaign promises to "restore excellence and integrity in government." Many of the stories describe the enmity and bitterness between Rolvaag and Keith.

There are also eight file folders of loose papers and photographs. These are housed in a gray archival box located within the larger Box 2. These include newspaper clippings, campaign literature and ephemera, a director's resolution from Northwestern National Life Insurance Company upon Pillsbury's retirement as chairman of the board (1981), and a booklet from Pillsbury Company on the occasion of Pillsbury's retirement from its board of directors (1980). Photographs include portraits of Pillsbury that were probably used for campaign purposes, and a reprint (1990) of an 1898 photograph of the University of Minnesota football team.