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Matt Liston is very passionate about his Chicago Cubs… ok, he’s obsessed with his Chicago Cubs. But after waiting 100 years for a ring who can blame him, right?

Liston does everything he can to get people on board the Cubs-Believe-Bandwagon… he shouts into a bullhorn that people should leave work at go to Wrigley, he spends $2,000 on a design for a World Series ring, he tries to get a permit for the Cubs World Series Parade, he sends the Pittsburgh Pirates Chicago pizza’s in hopes that they will eventually trade Kenny Lofton to the Cubs (which they actually do), he even goes to a bank in search of a $20 million loan so the Cubs can sign a couple big free agents. All the while he shuns employment, preferring instead to devote all of his time to his Cubbies.

In the end, predictably the Cubs lose.

It’s easy to say that Liston takes things too far in his support of a baseball team, but the sub-title of the movie is “A fan’s crusade,” and that’s just what Chasing October is. Liston doesn’t just buy a few bleacher tickets, he really puts his own well being on the line in hopes that it’ll put the Cubs over the top and they’ll finally be able win the World Series.

My first reaction to the movie was to think “wow, this guy’s nuts”… and really, within the context of the movie he is (making this movie has turned out to be a great career move, as he know works on documentaries for The History Channel and Discovery… but you don’t know that when you see him spending his last dollars on a design for a Cubs World Series ring). But being on my own nearly impossible crusade, and I couldn’t help but root for the guy, even if I knew what was going to happen at the end of the 2003 playoffs

The most interesting thing about Chasing October is it made me think those two terrible words “what if?” and I came to an interesting conclusion. If the Cubs had actually won the World Series, would Chasing October have actually been a documentary about being a Cubs fan? I think not… one day the Cubs will win the World Series, but in order to actually understand what it’s like to be a Cubs fan you have to understand loosing… loosing a lot… loosing in the most spectacular, unbelievable ways possible.

Mission accomplished… not only do the Cubs lose, but Liston also looses his girlfriend, his credit rating, and a lot of his sanity.