Events Newsletters Subscribe

Ad Categories: City Life

From the Outside In

by

I didn’t make it into the media pen, and I didn’t get to the party I was supposed to cover in time, so, at about 9:30 p.m., my election night coverage was looking pretty skimpy. Somehow, in all the crowds that were wandering around downtown, I managed to hook up with a few friends on Michigan Avenue, and we decided—wholeheartedly and foolishly—to cut to the center of the “overflow,” that is, the tens of thousands of people who were loitering on the eastern end of Grant Park looking at Jumbotrons and stepping on each other’s feet…

The Worry

by

In the formative stages of Barack Obama’s fame, no topic would make him or his aides more uncomfortable than his personal safety. When I first broached the subject, in July 2004, it was uncharted territory for the then-candidate for the U.S. Senate. Obama had just returned from the Democratic National Convention in Boston, where he had catapulted overnight into the zeitgest of Democrats across the country with his stirring keynote address…

Portrait of a Lady

by

Between the world wars, a beautiful, artistic woman named Bobsy Goodspeed stood at the heart of Chicago’s social and cultural scenes. Now, prompted by a salacious if glancing remark in a recent book, this forgotten woman re-emerges and opens the door on a vanished era peopled by painters and pianists, plutocrats and politicians—and an irresistible force named Gertrude Stein

The Teachings of Toot

by

Save for his mother, no one in Barack Obama’s life was more influential in shaping his character than his grandmother, Madelyn Dunham, known affectionately among the family as "Toot."

"I suppose I provided stability in his life," Madelyn told me matter-of-factly in her Honolulu apartment in October 2004, one of only two media interviews, by my count, that she has given…