I would have rooted for the Cubs. If you really know me, it probably comes as no surprise that, had the Cubs and White Sox met in the World Series this year, I would have rooted for the Cubs. I would have done it as a return to abandoned childhood allegiance, and also for my father, a true-blue Cubs fan who passed away last January and was unable to experience the amazing, eventful, sad-but-not-too-sad 2008 Cubs season.
I abandoned the Cubs at some point within a few years after the 1984 season. I know it's hard for Cubs fans who don't remember or weren't around for that season, but the play-off collapse that year, with the Cubs up two games, was far worse than what happened this year and in 2003 (when, many of us conveniently have forgotten, the Cubs were long-shots to begin with). I was heart-broken and felt all the other feelings that a lot of Cubs fans are expressing now.
But, over the next few years, attending a few Cubs games here and there while going to my first few Sox games, the heartache started to turn into a sense of pity for the entitlement that I had felt as a Cubs fan in 1984. You don't get to win simply because you want it badly, because you haven't won in a while, or because your ballpark is a really fun place to hang out. You don't get to win because you've lost badly before, or unfairly (in your eyes), or because you feel the experience of rooting for your team contains some essential magic. Baseball is magical. Baseball is fun. Baseball is tough. Baseball is real. Good teams win, and great teams beat them.
When the experience of rooting for a team starts to be more about desperation and entitlement than anything else, it ceases to be worthwhile. It saddens me to see a lot of Cubs fans still wearing their entitlement on their sleeves after this year's postseason failure.
I started to have more fun watching the Sox than I did watching the Cubs because a ballgame on the Southside was just a ballgame. It wasn't a small thing, mind you. It was important and loaded with implications, but it did not feel so burdened by past events, or by fear, or by fate, or by entitlement.
Anyway, that was years ago, and in the years since, my appreciation of the Sox has grown, and my appreciation for the Cubs has gradually returned. The people who have become involved in the Cubs as players, coaches and management truly have begun to change the perception of the team as a bunch of lovable losers. This has been especially clear in recent years under Jim Hendry, who really won me over when he made critical mid-season moves in 2003.
The Cubs and Sox both annoy me on occasion, but that's part of being a fan. Because I come from a generation before interleague play, I could always compartmentalize my passion for both teams. It's a lot harder to that now. I want them both to win. If they ever do meet in the World Series, I probably still would root for the Cubs though I wonder if that would change if the Cubs had already won a World Series by then. I don't know. I sometimes wonder if the Cubs were to win the World Series in the next few years against anyone, would I finally leave them behind? I don't think so. Like the Sox, they are a Chicago team, and I'm a Chicagoan. A fan of Chicago baseball.