This chapter surveys how the American Protestant ecumenical leader Stewart Winfield Herman, Jr., responded to the Nazi regime while serving as a pastor in Berlin from 1936 to 1941. Through an examination of Herman’s views of Hitler, the German Church Struggle, and Nazi persecution of the Jews, it weighs just how conflicted American Protestants, including leading Protestant ecumenists, proved on these matters. Based in the Nazi capital, Herman in particular captured the uncertain mind of American Protestants on German affairs. In Berlin, Herman expressed caution about Nazi totalitarianism, yet he still proved open to some of Hitler’s aims of national renewal and voiced his support of the German leader. He also hesitated to support the Confessing Church at first, fearing that the movement might cause enduring ecclesial schism. Finally, when Berlin’s Jews came to Herman seeking aid, anti-Judaism and Christian antisemitism led him and other Americans to be slow to offer their help. Overall, Herman’s interwar record illustrates how Protestant ecumenists were far from monolithic or fixed in their views of their era’s challenges. As their witness fractured, they struggled to meaningfully counteract Nazi fascism.