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The emerging alliance between Saudi Arabia, the United Arab Emirates, and Israel forms the centerpiece of the United States’ retrenchment strategy in the Middle East. Conventional wisdom in Washington suggests that such an alliance would serve as sufficient deterrent to Iranian ambitions, permitting the United States to draw down its hard and soft power investment in the region. Yet comity between the Gulf and Israel poses complicated challenges in the context of a longer-standing regional problem: a lack of popular support for ruling regimes. This paper has three parts. First, it examines the recent effects of U.S. efforts to formalize Gulf-Israeli cooperation against Tehran on local political outcomes in Lebanon, Palestine, and Jordan. Then, it explores an historical case study from the Lebanese Civil War. In 1983, the Reagan administration sought to establish tacit cooperation between Saudi Arabia and Israel against Syria, hoping to create conditions conducive to a U.S. withdrawal. As in the present day, U.S. officials failed to fully account for how local political dynamics could percolate up to the level of global security crises. Finally, the paper discusses the missteps and successes of the 1983 strategy, offering some suggestive illustrations of how the constant “retrenchment” refrain limits effective policy in the Middle East.