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The subject of this paper is part of my research book on the dilemmas and critical decisions faced by Israel’s diplomatic representatives and Diaspora Jewry in promoting and advancing Israel’s cause. Within the context of the historic role of the ‘shtadlan’ the paper presents and analyzes in depth the respective roles and contributions of Abraham Feinberg, Myer Feldman, and Max Fisher, close confidantes to US Presidents who, at critical junctures, sought their advice and services as back channel conduits and intermediaries in conveying messages between them and Israel’s leaders. Presenting primary Israeli and US documents, the paper accounts for the pressures, dilemmas and critical decisions taken by them, US and, Israeli leaders. The paper concludes with a perspective on extent to which the roles of Feinberg, Fisher, and Feldman were decisive.