When Esquire phoned at the end of October and asked me to profile Rahm Emanuel, I was both excited and slightly dubious. The last article they asked me to do never saw the light of day, and I told the mayor that we might go through the whole process and end up with nothing in the magazine. But he was game, and it wasn't like I could say No. It's Esquire. I spent four days with the mayor, and while I didn't feel like I exactly saw a candid slice of his working life—we spent a lot of time doing fuzzy activities such as reading to kindergarten classes and cutting ribbons at tot lots— I got to know him a little, to the degree that he can be known. It was a ton of work -- a very busy November, December and part of January — but it ended up nine full pages in the magazine. I learned much, got a chance to speak with people — David Axelrod, Garry McCarthy, Karen Lewis — I hadn't spoken with in depth before, and am satisfied with how it turned out. A few things didn't end up in the article that I wish were there — such as a fleeting encounter with the ever charmless Rich Daley — but I suppose those will find their way into print eventually.
Sister Rosemary Connelly was not pleased with the mayor of Chicago. The head of Misericordia, a beloved home to 600 people with Down syndrome and other disabilities, the eighty-three-year-old nun might not at first glance seem to be in a position to carry much influence over city politics. But this is Chicago, and Misericordia offers gold-plated care in a state notorious for its nightmarish residential institutions. The children and siblings of the powerful—politicians, TV anchors, lawyers, developers—are cared for there, and an A-list of Chicago’s leadership arrives on command, on bended knee and with an open checkbook.
It was 2011, and the City of Chicago had to bridge a massive budget deficit. Before he was even sworn into office, the mayor had announced that churches and social services would have to pay for the water from Lake Michigan like everybody else. With a stroke of the mayor’s pen, Misericordia’s water bill would go from zero to $350,000 a year. Sister Rosemary invited the mayor to speak to her fundraising breakfast. To his great credit, he showed up.
In his benediction, Misericordia’s Father Jack Clair felt inspired to bring a visual aid, a glass of water, to hold up and say, “Thank you, God, for the gift of water.” Then he paused. “Oh,” he said, looking at the mayor, “it’s not a gift anymore.”
At his turn to speak, the mayor returned fire. “I thought Jewish mothers had a corner on the market as it relates to guilt,” he said. The issue lingered, and two years later, when he appeared at a Special Olympics breakfast at the lush University Club, he spoke about the hard decisions that reality forces on leaders and about that time he made everybody pay for water, including Sister Rosemary, who was sitting in the audience. As soon as he finished speaking, he strode directly over to her and gave her a big hug. In a city known for political brawling, the mayor is a bastard’s bastard, profoundly profane and epically vindictive. But this was not a fight he relished. Give him a ward heeler or a senator or a president, no problem. But a nun?
“You know what the mayor says about me?” she had told the table, minutes before, smiling beatifically, her pleasant, deeply lined face ringed with an angelic halo of white hair. “He says, ‘Sister, you scare the shit out of me.’