There is a reason jokes about the Cubs and their incessant losing have become a pop culture staple. References to this ineptitude have been made in many places including Friday Night Lights, The Simpsons Halloween specials, Back to the Future and country music ballads. Read on to find out why.
Remember, like Wham told us in the ‘80s, “there’s no comfort in the truth, pain is all you’ll find.â€
1876 A baseball team is founded as the White Stockings. (They would also be called the Orphans and Colts before settling on the Cubs nickname in 1902)Â They win the first NL pennant as well as six of the first eleven titles. Talk about peaking early in life! It would soon go downhill from there.
1906 Cubbies set a record for wins in a season (116) that still stands to this day. No, I’m not kidding! As for the World Series that season, see “A brief history of the Chicago White Sox timeline to see how that one turned out.
1907-08 Cubbies become first team to repeat as World Series champions in baseball history! These were the teams of Three-Finger Brown, Orville Overall and the immortal Tinkers-Evers-Chance combination. The team’s website states: “what a decade for Cubs baseball which is exactly what it was†huh? Although this was their best decade, this redundant statement doesn’t seem to make sense. How did this get past the editors?
1918 Until 2004, this was the date that lived in infamy for the members of Red Sox Nation. The last victim before the 86 year drought? The Cubbies of course.Â
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1929 World Series, in which the Cubs yielded 10 runs to the Philadelphia Athletics in the seventh inning. A key play in that inning was center fielder Hack Wilson losing a fly ball in the sun, resulting in a 3-run inside-the-park home run.)
stock market wasn’t the only tings that crashed and burned in October of 1929.
1932 Cubbies win the pennant than watch as Babe Ruth toys with them calling his shot in game 3 of the series at Wrigley Field. Ruth pointed to a spot he intended to hit a homer and then promptly did so off Charlie Root. Yanks sweep Cubs in four.
1938 Yankees sweep Cubs in World Series again, dropping Chicago’s record in the Fall Classic to 2-7
1945 The infamous “curse of the Billy Goat†is born when a shop keep and his goat are denied entrance to the World Series which the Cubs lose to Detroit in 7 games. Supposedly a curse is placed on the franchise and the team has not won a pennant since. Whether the curse is real or not is debatable, but one thing is certain: this story has really been over-killed by the media.
1950s The first of three consecutive decades that yield no postseason appearances.
1969 The “Summer of Love†was two years prior, but no baseball team in Cub history is as beloved today as these chokers. They blow an 8 game division lead in August and finish 8 games out of first place. During a critical series against the New York Mets (the team which ended up winning the Cubs’ division) a black cat crosses Ron Santo’s path as he stands in the on-deck circle. The incident adds to the curse mystique.
1971-1982 Other than a 1964 trade (Cubs give greatest base stealer in history away to the rival Cardinals for Ernie Broglio), Not much of note happens here, except for lots and lots of losing.
1983 Manager Lee Elia unleashes a profanity laced tirade directed at the fans who show up at Wrigley day games (a night game is not played at Wrigley until 1988) just to boo him and his team. Amidst all the F words and other four letter words, Elia focuses on the point that these people don’t have jobs and asks why they come to Wrigley and ridicule him at his job? Do they actually have jobs of their own? Elia ends up being about ten-fifteen years ahead of time. It is not until the mid 1990s that globalization emerges and makes thousands of Chicagoans either unemployed, work-from-home consultants, or loathable trust fund babies who “work†at Wrigley Field in the summer.
1984 George Orwell himself could not have written a scenario this tragic. Cubs finally breakthrough postseason drought, and win first two games of the NLCS by a combined score of 18-2. They travel to San Diego only needing to win one of three to advance to the World Series. They take a 3-0 lead deep into the deciding game 5 but a historic collapse ensues, highlighted by Tim Flannery’s groundball going through first baseman Leon Durham’s legs in the late innings. The Cubs fail to win any of the three games in San Diego and Steve Garvey becomes as unloved by Cub fans as he is by all the women he never called back.
1989 Greg Maddux leads Cubbies to 1989 NLCS before losing 4-1 to the San Francisco Giants. Maddux was not tendered an offer after the 1992 season, he signs with Atlanta then wins a World Series there in 1995.
1998 Cub fans realize that the next Roger Clemens pitches for them. Rookie Kerry Wood ties Clemens for the record of strikeouts in a game in early May. Later in the season, Two steroided up power hitters from the NL Central resurrect interest in baseball as the Cardinals’ Mark McGwire and Cubs’ Sammy Sosa both break Roger Maris record for homers in season with 70 and 66 respectively ** The double asterisk is bult upon the asterisk placed for the previous record. The Cubs ride career years from mediocre journeymen such as Gary Gaetti, Jon Lieber, and Steve Trachsel into the pennant race. On the last day, the Cubs have a chance to clinch, but outfielder Brant Brown drops a routine fly ball and the Cubs are then forced to play one game playoff with giants to determine wild card. This moment becomes iconic for Cubs announcer and former third baseman Ron Santo. They win play-in game, but then get swept by the Atlanta Braves, led by good friend and ex-Cub Greg Maddux.
2001 Cubs are in first place at the break and 16 games over .500. They collapse in the second half and don’t finish 1st, not even second, but 3rd place.
2003 How did the Cubs finally get their first victory in a postseason series since 1908? By victimizing baseball’s answer to the Buffalo Bills, the Atlanta Braves. Atlanta has 15 straight trips to the postseason, but has only one title and three pennants to show for it. This was also the season of Sammy’s corked bat making him a national disgrace for exposing him as a cheater. And of course, this October brought us the complete implosion after being just five outs from the World Series during the NLCS. Game 6 eight inning gave us the appearance of Steve Bartman, Alex Gonzalez’s error of a routine ground ball, and Kyle Farnsworth’s lack of relief. The next night, Kerry Wood and company have a chance to make amends for the previous night’s fiasco, but the Cubbies also blow another lead in game 7 and watch the Marlins take the flag and then the series from the Yankees.
2004 Where do we begin? If ever a season encapsulated an entire century of misfortune it was this one. The Cubbies had a prolific off-season, improving the previous year’s playoff team immensely. One of the worst things in life is to have high expectations unfulfilled and this year was the paradigm. Sammy Sosa’s journey to the dark side of public opinion was made complete. The Cubs hold the wild card during the last week of the season, but somehow find a way to squander it against the lowly Reds. When Sosa decides to leave the park instead of play in the final meaningless game versus Atlanta, his infamous boom box is destroyed.
When Dusty Baker said the Cubs would no longer be “lovable losers,†he was right. This team (with a winning record) was as lovable as cold sores, traffic jams and mosquito bites combined. Along the way to their horrific collapse, members of the Cubs whine about the umpires being out to get them, broadcasters criticizing them, make retarded base running decisions, dial angry calls to the press box, injure themselves by childishly taking their frustration out on inanimate objects (Farnsy misses games after he hurts himself kicking an electric fan) and hit WAY too many of their home runs with no one on base.
2005 Exactly like the previous season in that the Cubs are expected to finish first but instead finish third, watch St. Louis take the NL Central division and the Houston Astros capture the wild card. Exactly like the previous season, ticket prices are increased by an astronomical amount and injuries keep the fans from seeing much of Nomar Garciaparra, Kerry Wood, and Mark Prior. To make things even more difficult for the fan, the Cubs policy of scalping their own tickets through their private brokerage company becomes even more profitable and therefore implemented.  Salt is poured in the ’05 wounds when their hated rivals, the Chicago White Sox, win the World Series.
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2006 Another year with high expectations, (Playboy magazine even predicted the Cubbies to win the world series!) results in manager Dusty Baker getting canned. They start out 14-10 before Derrek Lee gets injured and the decline begins. A May meltdown and June swoon of epic proportions follows. Another year of extremely high payroll isn’t enough to keep the Cubs from losing just under 100 games. Most of GM Jim Hendry’s acquisitions under-perform, putting him on the hot seat. There were numerous losses that were magnificent in nature…even by Cub standards. My favorite of all came on July 16, when the Cubs had a 5-2 lead over the National League leading New York Mets. The Mets scored 11 runs in the sixth inning, 8 of which on grand slams by Cliff Floyd and Carlos Beltran, the first time the Cubs have ever given up two grand slams in a single inning. The 11 runs were the most ever scored for a single inning in Mets franchise history. Salt is poured in the ’06 wounds when their hated rivals, the St. Louis Cardinals, win the World SeriesÂ
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 2007. Cubs get off to God-Awful start as the last remnants of the failed Dusty regime take a while to be swept out. After the All-Star break, the Milwaukee Brewers collapse laughably, the Cubs get hot and end up winning the weakest division in the history of the Major Leagues; maybe the weakest in the entire history of Western Civilization. Cubs are favored by many to win NLDS versus Arizona Diamondbacks, but fail to even win a game.
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