A charter member of the National League in 1876, the franchise traces back further to the Chicago White Stockings and was dominant in the league's earliest decades under player-manager Cap Anson. It took the Cubs name in the early 1900s and quickly became one of the sport's premier clubs, winning back-to-back World Series titles in 1907 and 1908. The club remained a frequent pennant winner through the 1910s, 1920s, and 1930s, but repeatedly fell short in the World Series itself, a frustrating pattern that would come to define the franchise for much of the twentieth century.

After its last pennant-era appearance in 1945, the Cubs sank into a long period of losing baseball, earning the affectionate but pointed nickname 'Lovable Losers,' punctuated by near-misses such as the 1969 collapse and a 1984 division title that ended in playoff heartbreak. A promising 2003 run ended in a crushing NLCS loss widely remembered for the Steve Bartman incident, extending the sense of franchise-wide futility. The hiring of executives Theo Epstein and Jed Hoyer in the early 2010s set in motion a methodical rebuild around young talent that culminated in the 2016 World Series championship, ending a 108-year title drought, the longest in major professional sports history at the time, with the club continuing to compete and retool in the years since under the ownership of the Ricketts family.