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Progressive educator, student of Thomas Dewey at the University of Chicago, served as head of the state Normal School at Oshkosh, Wisconsin, superintendent of the Felix Adler School of Ethical Culture in New York City and as head of teacher education in the city of Baltimore. The papers include extensive personal correspondence, scrapbooks, journals, writings and other materials concerning his professional interests. Correspondence includes letters from distinguished authors and educators.

The papers consist of extensive personal correspondence, scrapbooks, journals, writings and other materials concerning his professional interests. Included are, letters from distinguished authors and educators. Much of the collection relates to the progressive education movement and to Manny's career as an educator in Grand Rapids, Chicago, and Boxford, Massachusetts.

Consists of 7 outgoing and 344 incoming letters, largely from 1896-1903. Chiefly concerns Bool's financial support of anarchists and their publications, especially Benjamin R. Tucker and Liberty, and Moses Harman and Lucifer, the light-bearer, distribution of literature, particularly Bool's pamphlet Liberty luminants, the philosophy and activities of anarchist friends and acquaintances, notably John W. Lloyd, as well as personal and business affairs.

The Correspondence series includes several outgoing letters from Bool, but mostly consists of incoming letters. These primarily address Bool's financial support of anarchists and their publications, especially Benjamin Tucker and Liberty, and Lillian and Moses Harman and Lucifer, The Light-Bearer. Portions of the correspondence are concerned business matters as well as with anarchist philosophy and publishing, particularly the distribution of literature such as Bool's pamphlet Liberty Luminants. Anarchist and Labadie Collection founder Jo Labadie is well-represented.

The Archival series consists of one folder containing notes, typed and handwritten, concerning Bool's donation, via Jo Labadie, of pamphlets and booklets. Also included is a short memoir written in 1932 by Agnes Inglis, the original curator of the Labadie Collection, remembering Jo and "Mama" Labadie, Judson and Margaret Grenell, and Henry Bool.