San Antonio, Texas is the seventh largest city in the U.S. and the second largest city in Texas with a minority majority Latino population. It is the fastest growing of the top 10 largest cities in the U.S. Despite its Latino demographic dominance, San Antonio has only had three major Latino Mayors: Henry Cisneros, Edward Garza, and Julian Castro. This essay examines why this city has had only a few Latino mayors and what it takes for such candidates to win the mayoral office. This essay concludes the following findings: first, time and opportunity are critical to winning an election. Second, for a minority candidate to win the mayoral office, a broad collation is necessary. Third, serving on the city council is a necessary apprenticeship for winning office. This report is significant for understanding the political incorporation of Latino mayors into American politics. All three Latino mayors highlight the importance of consensus building, cooperation, and the absence of a confrontational spirit, which is key for Latinos to have a place at the table.