Since the White Sox haven't won a World Series since before the Red Sox last won (1917, vs. 1918 for Boston), they just assume that they're entitled to the same sympathy and underdog status that the Red Sox and the Cubs get. They just can't understand why 88 years isn't a bigger deal than 86 years.
Here are five reasons why.
1 - Success
The Cubs and the Red Sox have had more success than the White Sox. They've each had more appearances at every postseason level, and with the exception of the current White Sox run of 1sts and 2nds in a diluted division format, they've had them longer. Yes, both teams were miserable for long stretches, too, the Cubs in the 40s, 50s, and 60s, and the Red Sox in the 20s, 50s, and 60s. (From 1922-1932, the Red Sox finished last 9 times; nobody was more relieved to see Connie Mack coming than Boston fans.)
But this was largely after their legends were established. The Cubs won pennant after pennant in the World Series's early years, as did the Bosox. Their failures stood in contrast to their early success. And they've had their chances since. Which leads to...
2 - Heartbreaking Losses
The Bosox lost the World Series in 1946, 1968, 1975, and 1986. All in 7 games. They blew a 14-game lead in 1978. Everyone knows this. The Cubs may not have won since 1908, but they've played Detroit a couple of times, and ran into a couple of Yankees buzz-saws. They were one stupid frat-boy Steve Garvey home run away from a pennant in 1984. They blew a 9-game lead to the Mets in 1969.
The White Sox haven't taken a series to the final game in their entire history. Finding new ways to lose a 7-game series is the stuff of grand opera. Losing 4-2 to the Dodgers or 3-1 to the Orioles is par for a series.
3 - Curses
Look, you trade away Babe Ruth, whom everyone loves, to the Yankees, whom everyone hates, that's baseball mythology. Turning away an Old Man and His Goat is a Stephen King novel at worst, kinda cute at best. You can't win a series after that, and people just marvel at hidden powers.
You throw a series, get your whole team barred for life, destroy the integrity of the game, and force baseball to hand over powers not seen since Sulla to a second-rate judge in order to fix things, well, if you can't win a series, it's justice. No wonder they weren't missed. They were lucky still to be playing.
4 - Poets
The Red Sox get Bart Giamatti. The Cubs get George Will. The White Sox get...um..., yeah, right.
5 - Ballparks
Face it, right up until the moment in 2003 when Bartman interfered with Aaron Bleeping Boone's home run, or whatever, baseball fans were jazzed about a series played in Wrigley and Fenway. And not just because of the age, although that matters, too. Because of the continuity.
Look, nobody liked the old Comisky (once the novelty of fireworks for home runs wore off), and nobody likes the new Comisky. It's called "The Cell," ostensibly after US Cellular, but parks get the names they deserve. And it's not like Luke Appling or Luis Aparicio played there. If you're going to exorcise ghosts (or have them continue to haunt), the ghosts need to be there. The Cell has no ghosts.
Bonus Reason - 88 Years Is Too Long
In 1986, when the Red Sox hadn't won in 68 years, that was accessable. There were Red Sox fans who still could remember their last title. Sixty-eight years is a little less than a normal lifespan, so while Red Sox fans might die without seeing another title, they probably weren't going to die never having seen one. By 2004, when it was 86 years, I had stopped counting. Now, nobody remembered their last title, and nobody had been around for all 86 years of failure. So it was just a number.
Eight-eight's just a bigger number.
I'll probably be rooting for the White Sox against the Astros anyway. I still hold their orange construction-sign-uniform-plagued and Astro-turf-ridden history against them, for one thing. For another, I'm an American League guy. But really, other than that, I couldn't care less if the White Sox had been waiting 100 years for a title.
Hey, 2008's only 3 years away, Cubs fans.