Ever since the establishment of the Histadruth Ivrith of America in 1916, on the heels of several attempts to form a unified Hebrew movement in America, the pundits of the movement attempted to delineate the ideology, purpose and character of Hebrew culture in America. Three early Hebrew ideologues, Moshe Halevi, Kalman Whiteman, and Daniel Persky, discussed in this article, typified the ideological trends as they struggled with the concepts and means of preserving and promoting Hebrew culture in the diaspora, while American soil presented them with its unique and not too welcoming reality. The article discusses the ways they attempted to define Hebrew culture vis-à-vis the needs of American Jewry, as they perceived them, and how they coped with the American Jewish experience, while they were attempting to translate their ideology and lofty undertaking into practice. Some other aspects deal with topics that tantalized the Hebrew ideologues from the inception of the organization. Such are the question whether the Hebrew movement should cater to the elite or to the masses; should it emphasize cultural Hebrew activities, such as speaking Hebrew, or concentrate on the publication of books and literary journals; should the movement be part of the Zionists organization or outside of it.