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 for this affects both a leader and strategic planning system's focus. It will then briefly examine how the Joint Strategic Planning System (JSPS) changed five major ways from 1990 to 2012 before describing in greater detail the current system's key products and processes. The paper will then summarize the more significant ways each Chairman used this system during the past 2 decades and produced 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), and Pace (2005-07) and Admiral Mullen (2007-11). General Dempsey's current strategic planning...