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This paper will focus particularly on the academic and intellectual perspectives (in emigration) of Oskar Halecki, Czeslaw Milosz, Isaac Bashevis Singer, and Salo Baron. Thus, the paper will consider the cases of two creative writers, eventual Nobel winners Milosz and Singer; and also two academic historians Halecki and Baron. Clearly, the other interesting distinction is that among these four Singer and Baron wrote from Polish Jewish perspectives. The juxtapositions thus allow us to look at four cases that compare both literary and historical perspectives but also Jewish versus non-Jewish perspectives on the Commonwealth. Additionally, Halecki offers a clearly Roman Catholic perspective while Milosz offers a jointly Polish-Lithuanian perspective on the Commonwealth. Since these writers were working in America during the Cold War their depictions of the Commonwealth also partly reflect implicitly their perspectives on the contemporary communist government in Poland.