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The Cubs haven't won a World Series in 108 years. 

By Erin Flynn
October 07, 2015

Last season, the Cubs' first trip to the postseason since 2008 left cautiously optimistic Cubs fans thinking, "Could this be the year?"

The answer, yet again, was no. But this year the Cubs are back in the postseason again, this time with the best record in baseball. 

If Chicago were to win the 2016 World Series (knock on wood, Cubs fans), it would mark the team’s first championship in 108 years. That long century has been replete with opportunity, failure, hope and, most of all, heartbreak.

Since winning consecutive World Series in 1907 and 1908, the Cubs have lost their last seven World Series appearances. But the North Side’s playoff misery isn’t limited to the Fall Classic. As Chicago attempts to end its long drought, take a look back at the most heartbreaking moments that make the Cubs’ postseason slump so unique. 

1910–1945: Seven World Series defeats

Between 1910 and 1945, the Cubs appeared in seven World Series and lost them all. In that span, they lost to the Red Sox (1918), Tigers (1935), Athletics (1910, 1929) and Yankees (1932, 1938). The 1932 World Series featured Babe Ruth’s controversial “called shot,” and the 1929 World Series saw Cubs outfielder Hack Wilson lose two fly balls in the sun, leading to a three-run inside-the-park home run. 

But the most famous of those seven straight World Series defeats came in 1945.  

1945: The Curse of the Billy Goat 

In the Cubs’ most recent World Series appearance, the Curse of the Billy Goat was born. Up 2–1 in the series, the Cubs hosted the Tigers for Game 4 when Billy Goat Tavern owner Billy Sianis was allegedly asked to leave Wrigley Field because his pet goat smelled bad. According to team lore, Sianis then declared a curse on the team, saying, “The Cubs ain’t gonna win no more. The Cubs will never win a World Series so long as the goat is not allowed in Wrigley Field.” Whether it was black magic or just poor play, the Cubs would go on to lose the game and ultimately the series in seven games. The Cubs haven’t appeared in a World Series since 1945. 

1969: The black cat curse

The Cubs didn’t make the postseason in 1969, but the monstrous disappointment of the season makes it worthy of inclusion. Chicago led the National League East by eight games over the Mets on Aug. 19, and looked unstoppable heading into the season’s final days. Enter the infamous black cat. On Sept. 9, a black cat crossed the path of third baseman Ron Santo as he stood in the on-deck circle in Shea Stadium. From that day on, the Mets would surge forward to go 18–5. The Cubs went just 8–12, and the postseason drought continued. 

GALLERY: The plight of Cubs fans

1984: The Gatorade Glove dooms Chicago

In 1984, the Cubs’ postseason hopes may have been derailed by—wait for it—Gatorade. The Cubs claimed victories in the first two games of the best-of-five series, but collapsed in the final three games, giving the series win to the Padres. Cubs reliever Lee Smith surrendered a walk-off home run in Game 4, and first baseman Leon Durham watched a ground ball squirt past his allegedly Gatorade-dampened glove in the bottom of the seventh inning of Game 5. The Padres went on to score four runs to win the game and the series.

1989: Les Lancaster forgets the count

In Game 3 of the 1989 NLCS against the Giants, reliever Les Lancaster gave up a two-run, game-winning home run to Robby Thompson after forgetting the count and throwing him a fastball on 2–0. The Cubs wouldn’t win another game in the series, which they lost 4–1, and it would be nine years before they would return to the playoffs, only to be swept in the 1998 NLDS by the Braves.

2003: The Bartman incident

The Cubs led the 2003 NLCS three games to two over the Florida Marlins and were up 3–0 at home in the eighth inning of a contest that could have sent them back to the World Series for the first time in 58 years. Cubs fans are too familiar with what happens next. Steve Bartman, a Cubs fan sitting in the front row of the stands along the leftfield line, appeared to take away Moises Alou’s chance to complete a leaping catch in foul territory. Bartman deflected the ball from Alou’s glove, and the Marlins proceeded to score eight runs to win the game and complete the series win the following night.

2008: A second straight NLDS sweep

In 2015, the Cubs finished with the third-best record in the majors (97–65), which was only good enough to earn them third place in the NL Central behind the Pirates (98–64) and the St. Louis Cardinals (100–62). A 97-win season in 2008 earned them the best record in the National League and a ticket to the playoffs to face the Los Angeles Dodgers.

Despite the team’s best effort to exorcise its postseason demons by commissioning a priest to sprinkle holy water in the dugout, the Cubs couldn’t shake their postseason curse. Ryan Dempster gave up a grand slam to James Loney in the fifth inning of Game 1, giving the Dodgers the lead on their way to a 7–2 win in the series opener. The Dodgers swept the Cubs, who failed to gain a lead through the remainder of the series after Loney’s Game 1 blast.   

To add insult to injury, the Cubs were forced to pay Los Angeles to repair a water pipe that was smashed after Game 3. The pipe flooded the visitors’ dugout after the game.

The loss to the Dodgers marked the second year in a row the Cubs were swept out of the playoffs after losing the 2007 NLDS 3–0 to the Diamondbacks

GALLERY: The Plight of Cubs Fans

The Cubs will open their 2016 playoff campaign on Friday against the Giants. 

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