The centennial of powered flight was celebrated last year, yet the history of significant development of the aviation industry only spans the past 50 years. Aviation professionals can point to significant events in aviation with a relative ease. Many of these events have a direct cause and effect relationship with changes in safety and security regulations, policies and technology. There are also cases of technological development that have resulted in changes in operations, regulations and policies. Analysis of major events related to aviation safety, such as a specific accident, clearly show the corresponding outcomes across a wide spectrum. Less clear is an in-depth understanding of specific correlations between aviation accidents and their outcomes. This paper will examine how milestone accidents in aviation safety, from 1988 through 2002, have lead to significant changes in the areas of policy, regulation, industry and technology. The authors hypothesize that outcomes in these areas are characterized by reactive as opposed to proactive solutions. Methodology includes use of expert interviews and surveys combined with content review of U.S. Congressional record, Federal Aviation Administration regulations, including the code of federal regulations, news articles and trade journals.