In 2016, Colin Kaepernick spearheaded an activist movement by National Football League (NFL) players by “taking a knee” during the National Anthem before the start of NFL games. His goal was to raise awareness about police brutality and other oppression experienced by the Black community. These protests quickly became controversial and created a media firestorm. This research aims to understand his foundational education – graduating from both high school and the University of Nevada Reno with a nearly perfect 4.0 grade-point average – that laid the groundwork for his (re) education that spurred both his social activism and left him poised to enter a “free-world” economy equipped to make a life after football. Kaepernick’s experience contrasts with so many other Black men who exit the NFL without a strategy or tools for pursuing success beyond the NFL.