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 preparing to meet future challenges. This Paper will first describe the Chairman’s statutory responsibilities and strategic challenges, because this affects leaders and the focus of the strategic planning system. The Paper then briefly examines how the Joint Strategic Planning System (JSPS)changed in five major ways during the time period of 1990 to 2012 before describing in greater detail the key products and processes of the current system. The Paper then goes on to summarize the more significant ways each Chairman used this system during the past 2 decades to produce specific planning products, which is part of their formal leadership legacy. During this time the Chairman were Generals Powell (1989-93), Shalikashvili (1993-97), Shelton (1997-2001), Myers (2001-05), Pace (2005-07), and Admiral Mullen (2007-11). General Dempsey’s current strategic planning focus, since he became Chairman in October 2011, is also summarized. This leadership focus and concluding thoughts provide broad insights into how senior leaders have used the strategic planning system to respond to internal and external challenges. These leadership and management insights are related to the importance of strategic vision, planning system and process characteristics, decisionmaking styles, and organizational change.