This chapter examines the complex diplomacy between the United States and Israel during the administration of President George H. W. Bush and Prime Minister Yitzhak Shamir, with a particular focus on the road to the Madrid Peace Conference in 1991. It argues that US Secretary of State James Baker ultimately played a pivotal role in shaping the negotiations. Drawing on newly available archival materials from the George H. W. Bush Presidential Library, the Israel State Archives, and the American Jewish Archives, the chapter presents a detailed account of the tensions that characterized the period. It explores how emotions - alongside interests and strategy - shaped diplomatic behavior, particularly over the peace process and the request for US loan guarantees to support the absorption of Soviet Jewish immigrants in Israel. The chapter also investigates the parallel strains in US relations with American Jewish organizations. In contrast to accounts that treat this period as an aberration in the U.S.-Israel "special relationship," the chapter shows how it encapsulated the recurring frictions and deep-rooted affinities that have long defined the alliance. It also reflects on the broader historiographical and methodological implications of using newly declassified sources to reassess well-known diplomatic episodes.1