Much less the World Series.

Mostly because of poor management from top to bottom. When they've been able to assemble good talent (like recently) they have a poor team manager (dusty baker) and when they have a good manager they've had a bad front office. And on top of it Wrigley Field is more of a tourist point and/or the worlds largest beer garden, so the fans really don't push the teams management to have higher expectations.

I'd like to think it's because the Chicago Cubs and Wrigley Field are nostalgia incarnate. If the team were to rise above and win the pennant/World Series, the game of baseball would suffer a loss of innocence. The Cubs are commercialized today, but just imagine what would happen to their old-fashioned spirit after winning the World Series. Skyboxes, a dome, new owners, wealthier fans, and higher ticket prices.

Their charm would be tarnished. Chicago is a great city, sure, but it's known best for Al Capone and beer guzzling commentators. It's fitting that Chicago should have a jinxed ball club on the north side. The city stands for underdogs, cheats, and hard knocks. Sammy Sosa didn't truly fit in until he corked his bat (and lied about it). Only in Chicago would fans chide a player so lovingly after such a brazen act. Only in Chicago would you find such diehard fans, irrespective of W-L record. No other city is more deserving of the title, but to win it now would be sacrosanct.

True fans don't want the Chicago Cubs to win the pennant (much less the World Series). If the Cubbies became winners, we'd start to expect more and somehow love them less. Every season, the Cubs are at risk of commoditization but they pull through in the end and the subconscious wishes of fans reign.

Some would say Curse others would say lack of talent. I would venture that the Cubs as a team tend to start thinking too much when they get close to being succesful. In 1984 and 1989 they came within one game of being National League champions. And in 2002 came within 6 outs when the Bartman incident happened. With the White Sox winning this year the pressure to win a world series will be even greater for the Cubs. Maybe they need a new stadium (well they do cause Wrigley is falling apart)Or maybe they need some good luck.