Chicago Cubs Quizzes

The Chicago Cubs are a National League charter franchise, tracing to the 1876 White Stockings and a lineage that includes Cap Anson, the 1880s powerhouses, and the double-play combination of Tinker to Evers to Chance. They won the World Series in 1907 and 1908, then entered a championship drought that would last 108 years and become the most famous in American sports. Wrigley Field, opened in 1914 as Weeghman Park and home to the Cubs since 1916, turned ivy, brick, and daytime baseball into a brand. The 1918 pennant, the 1929, 1932, 1935, and 1938 flags, and the 1945 Series loss to Detroit kept hope alive without ending the wait.

Ernie Banks, Mr. Cub, never reached October but hit 512 homers and personified North Side loyalty. Billy Williams, Ron Santo, Ferguson Jenkins, and later Ryne Sandberg, Andre Dawson, and Greg Maddux (before his Atlanta peak) filled decades with individual brilliance. The 1969 collapse, the 1984 NLCS, the 1989 division title, and the 2003 Steve Bartman Game 6 against Florida layered new chapters onto the drought mythology. Lights arrived at Wrigley in 1988; the neighborhood remained the star as much as the roster.

Theo Epstein’s front office, hired after Boston’s 2004 curse-breaker, rebuilt the Cubs around Kris Bryant, Anthony Rizzo, Addison Russell, Javier Báez, and a rotation led by Jake Arrieta and Kyle Hendricks. In 2016 Chicago won 103 games, survived a dramatic NLCS, and faced Cleveland in the World Series. Down 3–1, the Cubs won three straight, taking Game 7 in extra innings after a rain delay. Ben Zobrist’s go-ahead hit and the final out ended 108 years of waiting. The 2016 title is the axis of modern Cubs history, the night Wrigleyville became a pilgrimage site for a championship that grandparents had only described.

Three World Series titles, two of them in the dead-ball era and one in extra innings in 2016, bookend a franchise that made waiting itself a culture. The Cubs remain baseball’s most visited historical brand: ivy on the walls, a manual scoreboard, and a fan base that treated 1908 as both wound and identity until 2016 turned the story into something rarer — a drought that actually ended.