Military leaders at many levels have used strategic planning in various ways to position their organizations to respond to the demands of the current situation, while simultaneously focusing on future challenges. This Letort Paper examines how four Chairmen Joint Chiefs of Staff from 1990 to 2005 used a strategic planning system to enable them to meet their statutory responsibilities specified in Title 10 US Code and respond to the ever-changing strategic environment. These responsibilities include: assisting the President and Secretary of Defense in providing strategic direction to the armed forces; conducting strategic planning and net assessments to determine military capabilities; preparing contingency planning and assessing preparedness; and providing advice on requirements, programs, and budgets. The Chairman's strategic planning system is a primary and formal way he executes these responsibilities as this system creates products to integrate defense processes and influence others related to assessment, vision, strategy, resources, and plans. This planning system integrates the processes and documents of the people and organizations above the Chairman, which are the President and Secretary of Defense, and the people and organizations he directly coordinates with, which primarily are the different military services and combatant commanders. In addition to influencing the nation's senior leaders, this system provides specific direction for many staffs that support these leaders. As such, this planning system is a key process that integrates the Nation's military strategy, plans, and resources that consist of approximately 2.24 million active, guard, and reserve forces and total defense outlays of $465B by 2005.