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Not long ago, you could find civic ads inside many of Chicago’s El trains, humorously touting the charms of the South Side in the form of a mock FAQ. In one of them, a mythical and provincially snobby North-Sider asked, “Will my cell phone work on the South Side?”

The joke: Chicago is a city divided, and to many of the city’s residents and visitors, the Chicago experience doesn’t go south of Roosevelt Road. A sense of entitlement on one hand and a sense of neglect on the other—they’ve informed the city’s divisions for as long as anyone can remember. They also, fittingly and predictably, inform the city’s baseball rivalry.

If you take a peek at the PECOTA-Adjusted Playoff Odds Report you’ll find that the Chicago Cubs, as of this writing, have a lofty 93.7 percent chance of making the post-season fray. Their Windy City label-mates, the Chicago White Sox, have an only somewhat-less lofty 78.2 percent chance of making it. Obviously, those two figures raise tantalizing possibilities.

It’s perfectly conceivable (if still statistically unlikely) that the Cubs and White Sox will meet in the 2008 World Series. If that comes to pass, it would put a blood feud that spans generations on the widest of baseball stages and is, I would argue, the most compelling rivalry in the game today. If Chicago’s two teams were to go at it with everything in the balance, it would certainly mean something—a lot, even—to the city and to the game of baseball. But what would it mean?

First, let’s acknowledge the rivalry’s uniqueness, at least among the interleague varieties. Think of the other border wars that aren’t Selig-era contrivances: YankeesMets, A’s-Giants, DodgersAngels. They lack a timelessness that’s essential to great rivalries. The Mets didn’t exist until 1962, the Angels weren’t around until 1961, and the A’s didn’t make it to Northern California until 1968, 10 years after the Giants made their own cross-country journey. In contrast, the Cubs and White Sox have been playing ball and sharing the same city since 1901.

Way back when, the Cubs certainly didn’t want the company. In 1901, they sued Charles Comiskey to enjoin him from moving his minor league team, the St. Paul Saints, to Chicago to join the fledgling American League. The Cubs’ maneuver failed, but they did make a couple of demands: Comiskey’s team couldn’t have “Chicago” in its name, and, at least in a sanctioned capacity, the team wasn’t allowed to play any games above 35th Street. In a withering rejoinder of sorts, Comiskey called his club the “White Stockings,” which once upon a time was what the Cubs were before they were the Cubs, and played his earliest games at old South Side Park, on 39th and Wentworth, just four blocks south of the line of demarcation. So there.

Like the rest of the AL, the White Stockings (soon to be called the “White Sox” by the local press) competed with the more established NL clubs by selling beer at their games and offering admission for a quarter, which was half of what the Cubs were charging at the time. With such charms, from the outset the White Sox were the team with which Chicago’s substantial working class identified, and that reputation holds today.

The two teams clashed in the 1906 World Series (the “Hitless Wonders” stunned the 116-win Cubs in six games) and over the years they met in the occasional Memorial Day charity exhibition. Mostly, though, they practiced hostility from afar, and since the teams rarely met on the diamond (and never for keeps from 1907 to 1997) Sox-Cubs was mostly a rivalry of identity. In 1917, when the Cubs moved from West Side Park to what was then Weeghman Park but eventually came to be known as Wrigley Field to settle into the increasing choice North Side, the rivalry took on a more distinct geographical division.

At 35th and Shields, where the Sox eventually settled into their new home, the odors of the nearby Chicago slaughterhouses, stockyards, and rendering plants wafted through the stands. Those attending games at Comiskey Park didn’t need Upton Sinclair to chronicle the excesses of the post-Gilded Age for them—they were terribly near at hand. In later years, the menacing presence of the Robert Taylor Homes was visible to the south. There were times when going to a game on the South Side was less “pastoral escapism” than it was “any port in a storm.” Still, Comiskey over the years hosted the Negro League All-Star Game for almost two decades, as well as Joe Louis’ championship victory over “Cinderella Man” James Braddock, and was the site of Larry Doby‘s major league debut. In so many ways, it was a symbolically important stage for black sports history, and though the place is gone, the by-the-bootstraps nature of the South Side isn’t.

These days, there’s still the contrast in environments. Abutting Wrigley are the hallmarks of gentrification: crowded bars, pricey townhouses, restaurants, shops, and the customary bustle of a neighborhood in demand. Take the Red Line a few miles south to U.S. Cellular Field, the antiseptic successor to Comiskey, and there’s, well… not much. Low-income housing, the constant whoosh of traffic on the Dan Ryan, blacktop parking lots, factories in the distance—little else accents the Sox’s current digs.

It’s fitting, in a way: the surroundings echo the reputations. The North Side is tawny and cosseted away. The South Side is hardscrabble and spare. As with any generalization, these have exceptions, but for the most part the truth holds. You can certainly find a similar dynamic in the Bay Area, with Oakland’s toughness contrasted with San Francisco’s refinement. However, those are two different cities, two cities in many ways as distinct as, say, Detroit and Prague. Chicago is one city, carved up in the extreme, but one city.

The Red Sox-Yankees rivalry, while more ballyhooed and ubiquitous, is an intra-league affair, and thus it lacks the promise of finality that a rivalry across leagues offers. The history of the Red Sox/Yankees conflict may be impressive, but these days it’s merely an object lesson in the banality of tribalism. What it also lacks is the backdrop of class and race, and that is what’s really at the heart of White Sox-Cubs.

The North Side certainly has a multi-ethnic population—Polish, Latinos, Arabs, WASPs, Pakistanis, Indians, and others—but it’s curiously light on blacks, which means it’s missing the most complex kind of American diversity. The South Side, meanwhile, has one of the highest concentrations of African-Americans anywhere. In fact, in the 19th century the area where one day Comiskey Park would stand was known as the “Black Belt.” Today, almost all South Side neighborhoods between 55th and 99th are predominantly black, and, in related matters, media consumers outside of Chicago know the South Side these days because of the rash of murders and as the adopted home of Senator Barack Obama.

What this means for White Sox baseball is that on most days you see more black faces in the stands at U.S. Cellular than you do at any other park. A black face at Wrigley? It’s likely a vendor or Ronnie Woo-Woo. (That’s not any sort of value judgment against the Cubs—neighborhood demographics are what they are, and teams are perhaps necessarily limited by them.) In part, that’s what makes Sox-Cubs so compelling. Each half of the city is an urban stew—the “good stew” as the murals in O’Hare correctly remind us—but each half teaches us how very different swaths of the same city can be. In that sense, there’s no other rivalry like it. It’s a rivalry freighted with the complications and terminal stand-offs unique to the American experience: black and white, rich and poor. Sometimes those delineations are overstated or even feigned, but there they are just the same.

Never mind the fact that the Cubs are flush against a centennial of failure: if it’s a Sox-Cubs Fall Classic, then that’s but one narrative among many. If the Sox and Cubs do meet in the World Series, expect each side to embrace the uncharitable renderings of the other. Sox fans will be crude, hostile, and dumb. Cubs fans will be pampered, weak, and privileged. Who among us doesn’t like to think of our enemies—real or imagined—as being some unfortunate mix of those words? That’s why the thought of it, Sox vs. Cubs, compels. It’s the most American rivalry you can find. That’s why it matters.

And maybe they’d give us some damned good baseball, too.

Thank you for reading

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