The rivalry between the Chicago White Sox and Chicago Cubs is one of the most intense in Major League Baseball. While the Cubs have traditionally received more national attention, White Sox fans take immense pride in their team’s grittier, blue-collar identity. The "Crosstown Classic" is an annual series between the two teams, and it always brings out passionate fan debates and electric atmospheres at Guaranteed Rate Field and Wrigley Field. The rivalry dates back over a century, with the most famous matchup occurring in the 1906 World Series, where the White Sox shocked the heavily favored Cubs. While the Cubs ended their championship drought in 2016 Jose Rodriguez Jersey, White Sox fans still take pride in having broken theirs first in 2005. Each matchup between these teams is about more than just baseball—it’s about city pride, generational loyalty, and Chicago’s deep sports culture.