Franchise knowledge
Chicago Cubs
Chicago National League Central
The Chicago Cubs are baseball’s most famous waiting story — and then the team that finally ended it. A National League charter club dating to 1876, three World Series titles, and more than a century playing in the same ivy-walled ballpark made the North Side a pilgrimage site long before the 2016 parade.
Below is a franchise overview: origins, eras, titles, legends, and the oddities that turned “Wait ’til next year” into a national punchline — and then into joy. When you are ready to test what you know, browse the full Chicago Cubs quiz collection or jump into recent seasons with the 2025 Cubs quiz.
Through the decades
Franchise Timeline
Scroll the milestones, then tap a year to read the story behind it.
Feb 2, 1876
NL charter franchise founded
Chicago joins the new National League as the White Stockings — the lineage that becomes today’s Cubs. William Hulbert’s circuit gave the club a continuous major-league identity that still defines North Side baseball.
Oct 14, 1906
116-win season ends in heartbreak
The Cubs win a modern-era record 116 games but lose the World Series to the crosstown White Sox — the only all-Chicago Fall Classic. Greatness without a ring becomes an early franchise theme.
Oct 14, 1908
Back-to-back World Series champions
Chicago repeats as champions by beating Detroit again. Nobody on the North Side knows it yet, but this will be the last parade for 108 years.
Apr 20, 1916
Cubs move into Wrigley Field
The club settles into Weeghman Park — later Wrigley Field — on the North Side. Ivy, brick, and manual-scoreboard baseball become the franchise’s permanent stage.
Oct 10, 1945
Last pennant before the long drought
Chicago wins the NL flag but loses the World Series to Detroit. Billy Sianis and the billy-goat legend attach themselves to the club for the next seven decades.
Sep 9, 1969
Black Cat at Shea Stadium
A black cat circles Ron Santo during a key series at Shea as the Mets overtake Chicago in the NL East. The moment becomes shorthand for another Cubs collapse.
Jun 23, 1984
The Sandberg Game
Ryne Sandberg’s multi-homer performance against St. Louis on national television announces the 1984 Cubs as must-watch baseball — and Wrigley as a summer cathedral again.
Oct 14, 2003
2003 NLCS heartbreak
Five outs from the World Series, Chicago loses NLCS Game 6 to Florida in extra innings. The night becomes the cruelest October memory for a generation of North Side fans.
Nov 2, 2016
Curse broken in Game 7
Down 3–1 in the series, the Cubs rally to force Game 7, survive a rain delay, and win in extra innings on Ben Zobrist’s go-ahead double. One hundred eight years of waiting end in Cleveland.
Oct 1, 2025
Return to October
The Cubs reach the postseason again with a wild-card berth and push into the division series before their run ends. Relive the roster and results in the 2025 Cubs quiz.
Chicago Cubs
Origins
The franchise that became the Cubs entered the National League in 1876 as the Chicago White Stockings — a charter member of the circuit William Hulbert built after the National Association collapsed. Cap Anson’s teams dominated the 1880s, establishing Chicago as an early baseball capital. The club cycled through nicknames — Colts, Orphans — before “Cubs” stuck in the early 1900s as young talent arrived.
Those turn-of-the-century clubs were dynastic. Led by the famous infield of Tinker to Evers to Chance, Chicago won pennants in 1906, 1907, 1908, and 1910. The 1906 team won a modern-era record 116 games — then lost the World Series to the crosstown White Sox in the only all-Chicago Fall Classic. The next two Octobers delivered back-to-back titles in 1907 and 1908, the second ending a run that would define the franchise for generations: nobody on the North Side would celebrate another championship for 108 years.
Wrigley Field opened in 1914 as Weeghman Park for the Federal League’s Chicago Whales. When the Federal League folded, chewing-gum magnate William Wrigley Jr. acquired the Cubs and the ballpark. The club moved in permanently in 1916. Ivy on the brick outfield walls, a hand-operated scoreboard, and decades of daytime baseball turned a North Side neighborhood into one of sport’s great destinations — a cathedral where history mattered more than luxury suites.
The origin story is therefore twofold: a 19th-century powerhouse that helped invent the National League, and a 20th-century institution that made patience itself a culture — until 2016 rewrote the ending.
Chicago Cubs
History
After the 1908 title, the Cubs remained competitive — pennants in 1918, 1929, 1932, 1935, and 1938 — but October kept turning cruel. Babe Ruth’s called-shot lore in the 1932 World Series at Wrigley, Hack Wilson’s record 191 RBI season in 1930, and Gabby Hartnett’s “Homer in the Gloamin’” in 1938 are peaks that never became parades. The 1945 pennant ended in a World Series loss to Detroit and, in popular mythology, a billy-goat curse that fans would cite for seven decades.
Postwar Chicago baseball belonged to Ernie Banks — “Mr. Cub” — whose sunny “Let’s play two!” optimism defined a franchise that rarely reached October. Banks won back-to-back MVPs in 1958–59, hit 512 home runs, and never appeared in a postseason game — a Hall of Fame career wrapped in North Side heartbreak. Ron Santo patrolled third base alongside him, a beloved star whose later broadcast voice became as familiar as the organ at Wrigley.
Contention flickered in 1969 when the Cubs led the NL East late in summer before collapsing against the Mets — a black cat on the field at Shea Stadium became the symbol of another near-miss. The 1980s brought Ryne Sandberg and the “Sandberg Game” at Wrigley in 1984, a nationally televised statement that the Cubs could punch back. Rick Sutcliffe’s Cy Young season and a division title followed, but San Diego ended the dream in the NLCS.
The 1990s and early 2000s mixed Sammy Sosa’s home-run chase with playoff teases. The 2003 club, five outs from the World Series, lost NLCS Game 6 to Florida in extra innings — a night forever tied to a foul-ball controversy in the stands. For a generation of fans, that game became the drought’s cruelest chapter after 1969.
Theo Epstein’s front office, hired after breaking Boston’s curse in 2004, rebuilt the Cubs through the farm system. Kris Bryant, Anthony Rizzo, Javier Báez, and a rotation led by Jake Arrieta and Kyle Hendricks peaked in 2016: 103 wins, a dramatic NLCS comeback against Los Angeles, and a World Series against Cleveland that required extra innings in Game 7 after a rain delay. Ben Zobrist’s tenth-inning double and the final out ended 108 years of waiting. Wrigleyville exploded; the phrase “Wait ’til next year” finally expired.
Recent seasons — rebuilds, retools, and a return to October — are covered in the 2023, 2024, and 2025 Cubs quizzes.
Chicago Cubs
Championships
The Cubs have won three World Series championships and 17 National League pennants. For most of the 20th century, the ledger’s cruel math was simple: plenty of flags, almost no parades.
- 1907 — Cubs 4, Detroit Tigers 0 (first title; Orval Overall dominates on the mound)
- 1908 — Cubs 4, Detroit Tigers 1 (back-to-back champions; Mordecai “Three Finger” Brown)
- 2016 — Cubs 4, Cleveland Indians 3 (Game 7 in extra innings; curse ends after 108 years)
Near-miss pennants stack high: 1918, 1929, 1932, 1935, 1938, 1945, 1984, 1989, 2003, and 2015. In Chicago, those years are stored beside the three trophies — especially 1945, 1969, 2003, and 2015, when the North Side could taste a parade and still went home empty. For recent rosters and results, start with the 2025 Cubs quiz.
Chicago Cubs
Oddities
Cubs lore is where baseball history, superstition, and Chicago neighborhood culture collide.
- 108 years: From the 1908 title to 2016, the drought became the most famous in American sports — a number printed on T-shirts, referenced in every national broadcast, and finally retired in Cleveland on November 2, 2016.
- The billy goat: After tavern owner Billy Sianis and his goat were turned away from the 1945 World Series, legend holds he cursed the club. Whether you believe it or not, the story shaped seven decades of fan identity.
- 116 wins, no ring: The 1906 Cubs went 116–36 — a winning percentage that still astounds — and lost the World Series to the White Sox. Greatness without October glory is a franchise theme.
- Homer in the Gloamin’: On September 28, 1938, Gabby Hartnett’s ninth-inning homer into the darkening Wrigley sky clinched the pennant. The phrase is still sung in Chicago bars.
- Let’s play two: Ernie Banks never saw a postseason game despite 512 homers and two MVPs. His optimism became the franchise’s public personality through decades of losing.
- 2003 foul ball: NLCS Game 6 against Florida turned on a foul popup near the left-field wall — and a fan interference controversy that still launches arguments at every Wrigley bar.
- Rain delay, Game 7: The 2016 World Series paused after nine innings tied 6–6. When play resumed, Chicago scored twice in the tenth to finish the curse. The delay itself is now part of the mythology.
- Day baseball: Wrigley was the last major-league park to host primarily day games for decades. The sun, shadows, and wind off Lake Michigan are still part of the home-field story.
The roster of memory
Notable Players
Legends, franchise faces, and the names every Chicago Cubs fan should know.
Ernie Banks
Mr. Cub
Two-time MVP and the eternal face of North Side optimism. Banks hit 512 home runs, never reached the postseason, and still became the most beloved Cub in history. “Let’s play two!” is franchise scripture because of him.
Ryne Sandberg
Ryno
Gold Glove second baseman whose June 1984 “Sandberg Game” at Wrigley announced the Cubs as national contenders. Sandberg’s power from the middle infield rewrote what the position could do in the NL.
Ron Santo
Nine-time All-Star
Five Gold Gloves at third base and a career spent battling diabetes in private while starring at Wrigley. Santo later became the voice of Cubs radio — as beloved in the booth as he’d been on the field.
Ferguson Jenkins
1971 Cy Young
Control artist who won the 1971 Cy Young with 24 victories and more than 30 complete games. Jenkins remains the standard for Cubs pitching excellence before the modern bullpen era.
Billy Williams
Sweet Swingin’
Consistent slugger who played 1,117 consecutive games for Chicago and won the 1972 NL batting title. Williams bridged the Banks era and the 1984 contenders with quiet Hall of Fame production.
Sammy Sosa
609 home runs
Home-run titan whose 1998 chase with Mark McGwire reintroduced baseball to the nation and made Wrigley a nightly highlight reel. Sosa’s corked-bat incident and later PED cloud complicated the legacy, but the power peak was undeniable.
Kris Bryant
2016 NL MVP
Top pick who rose through the Epstein rebuild and became the offensive centerpiece of the 2016 champions. Bryant’s MVP season and World Series homer made him the face of the curse-breaking core.
Anthony Rizzo
2016 captain
Emotional leader of the World Series club and the player fans hugged first when the final out landed. Rizzo’s defense at first, clubhouse presence, and clutch October at-bats defined the Epstein era in Chicago.