The Boss Collection contains correspondence, manuscripts, production material, photographs, business financial records, newspaper clippings, and ephemera related to the production of Boss Books Press' little magazines, books, and poem cards. The collection is arranged in four main series. The series publications includes correspondence and production material including photographs, offset negatives, mock-ups, galley proofs, original manuscripts, material samples, and costs for both published works and a handful of projects unfinished upon his death including work by Marcel Duchamp, Francesco Clemente, Man Ray, and Jean Cocteau for BossCards; the beginnings of Boss, issues 6-8; and a book about the surrealist painter Pavel Tchelitchew.

The business records have been organized into three series: editorial, distribution, and grants. Editorial contains all material related to the production of Boss Books Press including correspondence, catalogues, flyers, letterhead, copyright and ISBN forms, and unused and returned submissions; distribution contains material related to the distribution of published work including mailing lists, distributor correspondence, listings, and book fair material; grants contains application material and collected material for fulfilling grant requirements. All folder labels have been directly transcribed from the original folders; folder order has been imposed.