south side sox
Whatever one thinks of Barack Obama, he certainly looks cool in a T-shirt and a White Sox cap. Always a White Sox cap: I've thought carefully and can't remember him in a Cubs, Bears, or any other Chicago outfit. Which may tell a story, of sorts.
The White Sox have historically been the team of the working class, no nonsense, and primarily (but by no means exclusively) African-American South Side of Chicago--the place were Bad Bad Leroy Brown of the 1970s pop song dwelt. The Cubs, by contrast, play in a North Side neighborhood that is, or has at least become, somewhat fashionable and increasingly gay. Wearing one hat or the other in Chicago--unlike New York, no one ever wears an out-of-town item--instantly identifies you as being on one side or another of the cultural divide.
At times, the rivalry gets testy, as when a vendor outside Comiskey Park (the White Sox home) tried to sell us a shirt captioned, "Wrigley Field: The World's Largest Gay Bar." (I talked my son out of buying it by threatening to call him "Jew Boy" every time that he wore it. ) Presumably Obama would not share this rather uncouth and not-especially-tolerant sentiment. But given the flap over Rick Warren--not to mention events in California, where Black voters helped pass an antigay referendum--one has to wonder: is Obama taking yet another step back into the cultural "mainstream," or is he just looking good?