Democratic President Bill Clinton was known for his ‘Third Way’ approach, which consisted of centrist-leaning policies that included a largely laissez-faire economic philosophy, in contrast to the more interventionist beliefs of prior New Deal Democrats. President Clinton’s approach in this regard was especially relevant at a time when the American economy, specifically the technology industry, boomed in the United States. Along with his hands-off tendencies, however, President Clinton is also widely known for the antitrust case that was leveled against Microsoft Corporation during his presidency – an interventionist action. This begs the question of how his generally hands-off approach to regulation can be reconciled with the economic intervention attempted through the Microsoft case. This paper seeks to answer this question and argues that the common thread in President Clinton’s approach was a prioritization of innovation, which has set his antitrust and regulatory philosophy apart from both the traditional schools of economic thought that dominated the 20th century and from much of the views on technology industry regulation that succeeded his time in office. To do so, the paper analyzes regulatory paradigms of the 20th and 21st centuries, focusing specifically on the regulatory approach of the Clinton Administration towards the technology industry, including its antitrust case against Microsoft.