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This article longitudinally analyzes the strategic interaction between Turkey and the Kurdistan Workers’ Party (PKK) in their four decades of conflict. Using contemporary strategic theory as an analytical framework, it analyzes how the parties’ strategies –grand and military– and political objectives align. It finds that both parties have struggled with establishing (aligning policy, strategy, and resources) and, in several instances, maintaining a functioning strategy bridge. Static approaches that solely worked in a specific context and the absence of a strategy bridge have plagued both actors, thus perpetuating the ongoing conflict. The authors conclude that the conflict will likely continue unless one of the parties can create and maintain a working strategy bridge for an extended period.