Grace: President Obama and Ten Days in the Battle for America

by Cody Keenan

On that chilly February afternoon at Hyde Park Academy, in a neighborhood still mourning Hadiya Pendleton, Obama delivered a speech presenting an array of policies aimed at inverting inequality in places like the South Side. He was also scheduled for a brief surprise “drop-by” at a discussion circle with a group of teenagers in Chicago’s Becoming a Man program for at-risk youth—boys who showed potential but found themselves getting into trouble that could derail everything. Obama pulled up a chair and talked with them for an hour, ignoring staffers’ attempts to keep him on schedule. The teenagers gave voice to their lives and their struggles and how their world made it hard to do the right thing. He told them about growing up without a dad and the anger that came with it, about making bad choices and selling himself short, about being lucky enough to have people who gave him second chances and pushed him to make the most of himself. The boy next to Obama asked him, “Wait, are you talking about you?” A few months later, on Father’s Day weekend 2013, he brought the same students to the White House for lunch and a second conversation. For almost all of them, it was the first experience on an airplane. Now they were in the Oval Office with the first Black president. Before putting on their hand-me-down suits and ties, a few of the boys snuck out of their D.C. hotel and went to a convenience store. Once in the Oval, they gave Obama what they’d bought—a Father’s Day card they’d ...

SOON AFTER HE MADE ME HIS CHIEF SPEECHWRITER, OBAMA offered some sound advice: “Read James Baldwin when you’re stuck. Listen to John Coltrane when you’re not.”

“You know what they say about Miles Davis?” I did not. “It’s the notes you don’t play. It’s the silences. That’s what made him so good. I need a speech with some pauses, and some quiet moments, because they say something too. You feel me?” By that point, I did. I knew exactly what he was talking about. What brief pride I’d felt in a speech that was in the best shape it had ever been a week ahead of time was quickly replaced by regret—regret that I’d been so consumed with making sure everything was in there that it made him complain that everything was in there. “Good,” he finished. “Like I said, we’re in great shape. I don’t want you to do any work tonight. I want you to go home, pour yourself a drink, and listen to some Miles Davis. And tomorrow, take another swing at it.” He pointed his fork at me. “Find me some silences.”