The Chicago Cubs have not won a World Series championship since 1908, and have not appeared in the Fall Classic since 1945, although between their postseason appearance in 1984 and their most recent in 2015, they have made the postseason seven times. 107 seasons is the longest championship drought in all four of the major North American professional sports leagues, which also includes the National Football League (NFL), the National Basketball Association (NBA), and the National Hockey League (NHL). In fact, the Cubs' last World Series title occurred before those other three leagues even existed, and even the Cubs' last World Series appearance predates the founding of the NBA. The much publicized drought was concurrent to championship droughts by the Boston Red Sox and the Chicago White Sox, who both had over 80 years between championships. It is this unfortunate distinction that has led to the club often being known as "The Lovable Losers." The team was one win away from breaking what is often called the "Curse of the Billy Goat" in 1984 and 2003 (Steve Bartman incident), but was unable get the victory that would send it to the World Series.

When was the last time the Chicago Cubs win a World Series championship?