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In March 1918, the Massachusetts Branch of the Jewish Welfare Board sent a letter to the organization’s national headquarters asking a seemingly straightforward question: They had been contacted by a Dr. Shohan, who was working to recruit young men from the United States, to serve in a Jewish Battalion fighting in Palestine under the British. He asked permission to set up his headquarters at the Jewish Welfare Board’s office. Would this be ok? The answer to such a question was not obvious. What would it mean for Jews in the United States to assist in the recruiting efforts of another combatant country even though the young men in question might be eligible for service in the American Expeditionary Forces? What were the implications of supporting the creation of a Jewish Battalion under the British, while adamantly insisting that Jews not be segregated within the American military? And what might result from communal sanctioned displays of enthusiasm for Jewish nationalism in the midst of the American war effort? This paper will examine American Jewish responses to the Jewish Legion and to different expressions of Zionist sympathies during the war. It will consider both the appeal of the image of the Jewish Legionnaires as Maccabean soldiers, as well as the very real concerns faced by Jewish leaders as they navigated the demands of loyalty made by the wartime American state.