On September 22, 2020, President Donald Trump issued Executive Order 13950: Combating Race and Sex Stereotyping. This order stopped federal agencies, federal grant recipients, and government contractors from conducting training in the workplace that involves "stereotyping" or "scapegoating" based on sex or race, specifically banning discussions of critical race theory and white privilege. The United States District Court for the Northern District of California issued a preliminary injunction on December 22, 2020, banning the enforcement of the order, and, on January 20, 2021, President Joe Biden, during his first day in office, revoked the order. However, this did not signify the end of Executive Order 13950's importance. While this executive order is atypical because it utilizes government procurement as a vehicle to enact socially conservative policies, it continues the troubling trend of presidents using executive orders to regulate government contractors. This Note will first analyze three problems with the defunct executive order: (1) the executive order was bad policy; (2) it violated the United States Constitution; and (3) most importantly, the executive order itself is the wrong mechanism to enact social change and regulate government contractors. Second, this Note will explain that the rise and fall of Executive Order 13950 exemplifies the turbulent nature of regulating government contractors through executive orders. Instead of relying on such orders, government officials should regulate labor and employment requirements on government contractors through legislation because such measures are longer lasting, give interested parties the opportunity for input, and undergo more deliberate considerations before enactment. [ABSTRACT FROM AUTHOR]