October 14, 1908: The Chicago Cubs beat the Detroit Tigers 4-1 to win the World Series for the second year in a row. There are a total of sixteen teams competing for the title.
It's 2001, and the Chicago Cubs have had a mighty good year. Of course, watching popular St. Louis Cardinals slugger Mark McGwire spend half the season on the bench due to injuries probably helped things along, but regrettably it didn't help enough. The Cardinals are duking it out with the Houston Astros for first place in the division, leaving the Cubs in third and no longer a contender. Cubs fans' hearts are hurt, but not broken. Everyone knows we're used to it.
October 10, 1945: The Cubs play their seventh game against the Detroit Tigers in the World Series. They lose, nine runs to three. It's not the last time the Tigers play in the World Series. It is, however, the last time for the Cubs.
I remember reading a comic book many years ago (Excalibur, to be precise) where a teenage Chicagoland-born superhero (Kitty Pryde) is awkwardly placed in a British prep school. At one point in a field hockey game, the teenaged superhero invokes the name of the Chicago Cubs to try and rally some team spirit. The class snob rebuffs her by saying, "I know a few things about baseball. Your precious Cubs, they always lose." It was something of a turning point for me to realize that even people who know next to nothing about baseball as a game know of the Cubs' tragic reputation.
October 2, 1969: The Cubs finish second in the National League's East Division, eight wins behing the New York Mets. It's the best finish they've had since winning the National League Championship in 1945.
The Cubs aren't really losers, not like the Baltimore Orioles were with their history-making 21-game losing streak at the start of the 1988 season. But even the Orioles managed to win the World Series earlier in 1983. Meanwhile, the Cubs -- season after season, ever since 1908 -- have usually managed to get close but never close enough to the top. Perhaps it's psychological, but I think it's just dumb luck. There's got to be one team, somewhere, that consistently fails to make it to the top. It just so happens that they live in Chicago.
October 5, 1972: The Cubs finish second in the National League's East Division, eleven wins behind the Pittsburgh Pirates, the same team who beat them for the division title in 1970.
"Slammin'" Sammy Sosa makes the Cubs exciting these days. In 1998 he and Mark "Big Mac" McGwire were both in pursuit of a new Major League record, the most home runs hit in a single season. Roger Maris had held the record since 1961 with 61 homers; Babe Ruth had been the first to his 60 in 1927. When the season ended, however, Sosa was at 66 while McGwire had crested 70. Once again, the Cubs had to settle for second-best. The fact that McGwire's St. Louis Cardinals were the Cubs' longtime rivals didn't help any.
October 7, 1984: In a seventh-inning rally, the San Diego Padres beat the Cubs in the fifth game of the National League Championship series, winning 3 games to 2.
When Harry Caray died in February 1998, long before that season started, the entire baseball community mourned. Harry wasn't just an announcer, he had over the years become the heart and soul of the Chicago Cubs and of baseball itself. Nobody sang "Take Me Out to the Ball Game" like he did, proclaimed "Holy Cow!" like he did, made fans feel like they belonged to something great like he did. Near the end of his career he was old, his voice was no longer sharp, his glasses were so thick you wondered how they could help, but he was still Harry, and it's hard to imagine anyone who loved baseball like that. He wasn't beautiful, not by a long shot. But he was a fan, and you could always count on him remaining one.
October 9, 1989: After a much-celebrated first-place win in their division, the Cubs surrender the National League Championship to the San Francisco Giants in a 4-1 series.
It's 2003, and the Cubs have had a mighty good year. Young pitchers Kerry Wood and Mark Prior are widely credited as the strongest elements of the team's success, although Sammy Sosa's strong hitting hasn't let anyone down yet. When they win the Central Division, fans are overjoyed, even though the Cubs have the lowest win/loss ratio of any Championship contenders. When they beat the Atlanta Braves in six games, the first postseason series the Cubs have won in 95 years, people across the country begin speculating on whether the "loveable losers" of American baseball may finally make it to the World Series....
October 15, 2003: Playing in their first Championship series ever -- the Championships weren't organized until 1969 -- the Cubs soon took the lead three games to one over the Florida Marlins. They then lose the final three games.
Nobody chooses to be a Cubs fan. It's something you're born into by virtue of growing up on the north side of Chicago. (South siders root for the White Sox instead.) But there's something unique about Cubs fans that you almost never see in professional sports. Because of their history, there's no such thing as a fair-weather Cubs fan. Cubs fans are loyal because they love their team, and they remain loyal year after year. Wrigley Field fills its stadium at times when other teams' stadiums are half-empty, no matter how the Cubs are doing that year. If and when the Cubs finally head to the World Series again, Chicagoans who find themselves suddenly rooting for a team they mocked all their lives won't be able to get tickets even at scalper's prices. The real fans will already have them all, and will hoard them all for friends and family out of good old-fashioned spite.