["Middle East Policy, EarlyView. ", "\nAbstract\nThe US‐Israeli war on Iran appears to demonstrate the perils of a transactional diplomacy that dismisses the rules‐based, liberal international order in pursuit of American dominance. Much of the growing literature assumes transactional diplomacy will be a temporary, Trump‐driven departure from traditional, values‐based statecraft. By contrast, while we harbor reservations about transactionalism, we refuse to embrace such predetermined conclusions. Moreover, we do not believe transactionalism will fade after Trump, as a number of states are embracing it, especially in the Middle East. Despite this, to our knowledge, there has been no effort to assess transactionalism through case studies from the region. This article provides a comparative evaluation of transactional and traditional diplomacy through a cost‐benefit analysis of their objectives and methods. It then examines two examples of transactional diplomacy, the Gaza peace plan and US support for post‐Assad Syria. Our findings provide leverage to analyze Washington's 2026 war on Iran. The evidence indicates that the conflict should not be interpreted as a failure of transactional diplomacy, since the administration never genuinely engaged in reciprocal bargaining. Instead, it demonstrates that transactionalism is of limited use in crises defined by maximalist demands and rapid escalation.\n"]