Free Never a City So Real by Alex Kotlowitz Page A

wasn’t right.” The demolition of the single runway at Meigs Field, an airport for private planes, was an old-school move by a new-school politician. Earlier in the summer, under cover of night, the mayor had sent a battalion of backhoes and bulldozers to scar the runway with gigantic X-shaped trenches, rendering useless this small lakefront airport—which he wants to rebuild as a park. King Richard the Second, Chicagoans joked—a reference, of course, to King Richard the First, his father. (Between the two of them, they’ve governed Chicago for thirty-five of the last fifty years.) The thing about it, I argue with Reed, is that the mayor was probably right: This prime piece of lakefront property belongs to the people, not to the few who can afford their own airplanes. “Yeah, but it ain’t the right way to go ’bout things,” he argues.
    Of a smiling alderman who is followed by fifty supporters wearing T-shirts bearing his name, Reed remarks, “They should be throwing milk cartons at him.” When the fifty-four-year-old county treasurer, Maria Pappas, jumps out of a convertible to spiritedly twirl a baton, Reed laughs good-heartedly, and applauds out of admiration. A number of white politicians drive by, each accompanied by a black friend or coworker; it seems like a statement—“I have friends who are black”—from another era. But it’s the high-stepping, boogying marching bands that get the crowd worked up, especially the South Shore Drill Team, which stops every couple of blocks to perform their highly choreographed and high-spirited routine.
    The Jesse White Tumblers march by; they’re a group of kids from Cabrini Green, another public-housing complex, who can be seen at events throughout the city, including at halftime during Chicago Bulls games. “Oh, shit,” exclaims Reed. “There’s gonna be some jumping now.” A woman eager to see the tumblers gives me a flirtatious look and climbs onto my milk crate alongside me, her buxom body pressed against mine. A young man hawking bottles of water and sporting a tattoo on his forearm of his deceased pit bull (which, he later tells me, was named “Cats”) winks at my good fortune.
    Reed climbs down and tells me he’s got to get to work. But there are no takers, so he instructs me to sit down and begins to sketch me. Passersby stop to peek over his shoulder; he points to my eyes and eyeglasses and observes, “All this should be smaller, but it’s a nice drawing of a white guy.” A teenage girl takes a look and reprimands Reed. “His glasses ain’t square,” she tells him. He erases the glasses and makes them circular.
    A mother comes by with her five-year-old daughter, sits her on my milk crate, and asks—really, tells—Reed to draw her. The child sits surprisingly still, a bag of blue cotton candy in her lap, and then it starts to rain, so the mother and I hold a sheet of plastic over Reed’s head as the girl pushes the cotton candy under her leg to keep it dry. “What d’ya think?” he says, holding the sketch up for the mother to see. She examines the sketch, which is marked by raindrops. “Where her buttons?” she asks. Reed looks perplexed. “On her shirt,” she says, pointing to her daughter. Reed looks over. He’s missed the shirt’s buttons, so he draws them in, and because of the rain he charges the mother five dollars instead of the usual seven.
    â€œI’m ready to get outta here,” Reed tells me after a couple of hours. Business is slow. We walk north on King Drive, stopping occasionally to watch a high school marching band, then the Broken Arrow Riding Club (a collection of African-American horsemen and -women), then a flatbed truck bearing Jesse Jackson and members of his Operation PUSH, and finally a float of black owners of McDonald’s franchises.
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    We head west on 45th Street,