Veteran Chicago political reporters such as James Ylisela Jr. go back a long way with Richard M. Daley. “I covered Daley when he ran and lost in 1983,” says Ylisela, who has subsequently followed the mayor through six terms. With the end of the reign approaching (presumably), Ylisela argues that Daley can now use his clout without political consequences. In Mayor Daley’s Bucket List, Ylisela poses a ten-item to-do list for the time before Daley leaves office. “He may be in that position of saying, ‘I’m going to spend the next four years making the tough decisions,’ ” Ylisela says. “He can simply do what’s best for the city and finish with a flourish.”

As the editor of Chicago magazine’s sister publication, Chicago Home + Garden, JAN PARR sees a lot of remodeled houses. The Indiana residence she writes about in this issue’s Reporter, “The Money Pit,” is in a class by itself. “It’s by far the most extensive renovation I’ve ever covered,” she says. “They rebuilt it without tearing it down.” The house, an exhibit at the 1933–34 Century of Progress exposition, fell into disrepair after being relocated to the Indiana Dunes. Parr also wrote this month about Buchanan, Michigan, for A Harvest of Color.

“Wherever I went and whomever I talked to, everybody had an opinion,” says BETH WILSON, speaking of the research for Reversal of Fortune, her article about the rise and fall of the fashion boutique Jake. “Either they were supportive and empathized [with Jake’s owners] or they sure didn’t.” Jake quickly built a national reputation selling collections by hot young designers, but when the economy turned south, money to pay those designers ran short, leading to a contentious bankruptcy. As the Chicago correspondent for Women’s Wear Daily, Wilson had a front-row seat as the story developed. “I’m not sure which was more notable: the meteoric rise [or the] well-documented, very dramatic fall,” she says.

“After Michael Jordan retired, he was the biggest sports star in town,” says SHANE TRITSCH of Sammy Sosa, the former Cubs right fielder and subject of Sammy Agonistes. From 1998 until about 2002, Sosa’s power-hitting and exuberance made him a hero. But as the home runs slowed and whispers about possible steroid use crescendoed, his popularity cratered. Tritsch, Chicago’s managing editor, examines this painful arc, in which he recognized his own feelings. “I used to be one of those people who sat in the right-field bleachers and cheered for Sammy as hard as anyone,” he says.

The illustrator CHRIS LYONS (left), based in Pittsford, New York, created the image that opens Mayor Daley’s Bucket List: a portrait of Daley with unfilled paint-by-numbers spaces. Lyons’s self-described “slightly painterly, slightly retro” style, using sectors of solid colors to show depth, meshed perfectly with the paint-by-numbers conceit. “I love exploring light and exploring shadows,” Lyons says. The assignment arrived soon after he created 16 bug tattoos for Target. “One of the great things about illustrating is you just don’t know what’s coming next,” he says. His work has appeared in The New York Times, the Chicago Tribune, and Time magazine.

Photography: (Ylisela Jr.) Courtesy of James Ylisela Jr., (Parr) Katrina Wittkamp
Illustration: Chris Lyons