Much debate and national soul searching has taken place over the value of the Space Shuttle which first flew in 1981 and which is currently scheduled to be retired in 2010. Originally developed post-Saturn Apollo to emphasize affordability and safety, the reusable Space Shuttle instead came to be perceived as economically unsustainable and lacking the technology maturity to assure safe, routine access to low earth orbit (LEO). After the loss of two crews, aboard Challenger and Columbia, followed by the decision to retire the system in 2010, it is critical that this three decades worth of human space flight experience be well understood. Understanding of the past is imperative to further those goals for which the Space Shuttle was a stepping-stone in the advancement of knowledge. There was significant reduction in life cycle costs between the Saturn Apollo and the Space Shuttle. However, the advancement in life cycle cost reduction from Saturn Apollo to the Space Shuttle fell far short of its goal. This paper will explore the reasons for this shortfall. Shortfalls and lessons learned can be categorized as related to design factors, at the architecture, element and sub-system levels, as well as to programmatic factors, in terms of goals, requirements, management and organization. Additionally, no review of the Space Shuttle program and attempt to take away key lessons would be complete without a strategic review. That is, how do national space goals drive future space transportation development strategies? The lessons of the Space Shuttle are invaluable in all respects - technical, as in design, program-wise, as in organizational approach and goal setting, and strategically, within the context of the generational march toward an expanded human presence in space. Beyond lessons though (and the innumerable papers, anecdotes and opinions published on this topic) this paper traces tangible, achievable steps, derived from the Space Shuttle program experience, that must be a part of any 2l century initiatives furthering a growing human presence beyond earth