It is supposed to be common knowledge that Major League Baseball’s “color line” was broken by Jackie Robinson. Leading up to that historic event, baseball team owners had collectively forged an unwritten agreement to maintain that their league was to be played by white players. However, players such as Moses Fleetwood Walker, Charlie Grant, and Rube Foster challenged the unofficial enforcement of the color-line in the major leagues and consequently faced varied forms of public backlash, all before Robinson’s tumultuous debut in April 1947. And Negro League teams and barnstorming clubs experienced significant popularity and financial success. This paper will seek to recognize the largely unknown history of “color line” breakers prior to Robinson as well as to address the status of race-based discrimination in baseball in the post-Robinson era, leading up to today. Drawing on works by Rob Ruck, Adrian Burgos Jr., David J. Leonard, as well as from contemporary journalism, I will compare and contrast racial divides in Major League Baseball across nearly a hundred years; I will explore how Ben Chapman’s verbal berating of Robinson in 1947 compares to the Fenway crowd’s hateful jeers towards Adam Jones in 2017, and how MLB exploitation of talent from the Negro Leagues served as a precursor to the way it currently “acquires” and compensates international players. Proving the well known adage that “history tends to repeat itself,” this thesis demonstrates the persistence of both covert and overt discriminatory practices employed by major league baseball regarding race, and decisively argues that discriminatory practices, transactions, and environments are still prevalent in the league today. This research contributes to an ongoing dialogue regarding the “white way” to play baseball, decreasing participation rates by players of color, and systemic discrimination in the hiring and gatekeeping practices of Major League Baseball.