I'll be rooting for the Chicago Cubs in the World Series. They are playing the Cleveland Indians. Both clubs have had problems with the Fall Classic. The Indians haven't won the World Series since 1948, and the Cubs haven't won it all since 1908.
Chicago's quest reminds me very much of the Red Sox quest to win it all back in 2004. I remember how incredible it felt to win the World Series. Baseball was the first professional sports that I followed seriously. I remember the heartbreak of 2003, and the glorious finish that was the 2004 ALCS and World Series. The Red Sox swept the St. Louis Cardinals in that World Series, which seemed appropriate since they came back from being down three games to the New York Yankees in the ALCS.
Chicago has also got the best record in baseball. It's not often that the best team in baseball gets to win the World Series. The last time this was in 1998, with the NY Yankees. I like to root for favorite when there is excellence on the line (though please, don't talk to me about Super Bowl XLII). I also like to root for connections. In the case of Chicago, there's pitchers Jon Lester, John Lackey and their General Manager, Theo Epstein.
There are some X-factors for the India though. Terry "Tito" Francona is the manager for the vaunted Indians, and Tito managed the 2004 and 2007 Red Sox to their World Series victories. The other X-factor: because the National League lost to the American League in the All-Star Game, the Indians will have four games at home, and Chicago will only have three. (The series will have two games at Cleveland, then three at Chicago, then two more at Cleveland.)
It will be a great series, one that feels like a win-win for neutral fans. Cleveland is still buzzing about the Cavalier's NBA Championship, and winning a baseball championship will instantly add that city as a contender for Titletown. Chicago has had great success in my memory with all their sports, including a World Series for the Chicago White Sox.
In the end, I root for the lovable losers. I root for the dedicated fans who've been dying for a break. I root for a team that plays its games in a bandbox not unlike Fenway Park. I root for hexes and curses being broken and debunked. Let's get it done, Chicago!