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The twentieth-century was a period of adaptation and change for Portland’s Jewish Community. Orthodox Jews were bound by strict laws and traditions that governed their faith and their culture. However, when faced with the values and norms of traditional American society, Portland’s Orthodox Jews had to negotiate between assimilation and maintaining their religious practices and identity. Early in the century, changes were welcomed as a way to assimilate into American society and to take advantage of economic opportunities. However, as more Orthodox Jews identified themselves as Americans, some members of the religious community believed that important values were being compromised. This article focuses on Portland’s Shaarey Tphiloh Congregation, which in many ways parallels the experience of Orthodox Jews across the United States. Michael R. Cohen is Visiting Schusterman Professor in the Jewish Studies Department at Tulane University in New Orleans. His specialty is American Jewish History.