Portrait of a Lady

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

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…

The Jealousy Factor

It’s hard to say exactly when the moment arrived, but well into Wednesday’s final presidential debate John McCain must have realized that he was not “whipping” Barack Obama’s “you-know-what” and, in fact, probably was starting to fall behind on points.

That’s when it kicked in, and you could see it wash over McCain’s face—that feeling of distaste for Obama that I’ve witnessed in so many of Obama’s political opponents (and some others) over the years. Call it jealousy or call it disdain, but Obama can readily elicit this emotion from people who come into contact with him…

The Fear Card

As the first biographer of Barack Obama, I have often found myself in a position where few journalists find comfort: defending the honor of a politician.

Yet, over the past 14 months, ever since the release of my biography of Obama, I have fielded countless questions about Obama that clearly have been based in ugly racial or religious distortion, and I have felt it my obligation to help set the record straight. In doing so, occasionally I have been accused of being an Obama sympathizer. But if that’s the price of spreading the truth, so be it…

ALDS Game 2: Sox at Rays

The Ump says C.B. Buckner blows, The Fatalist admires Uribe’s chin hair, The Delusionist fields hate mail, and The Time Traveler is lost in the wilderness. Here, our analyses of ALDS Game 2

The Temperament Debate

Can a contest for the world’s most important public office get any more uncertain than this? For all of his seriousness and sobriety, Barack Obama consistently seems to find himself playing the straight man in these unhinged political acts.

First, Sarah Palin and her hockey mom-with-lipstick sent the political contest hurtling into bizarro world, at least for a while. Then, the country’s credit and mortgage crisis evolved into a full-blown threat to the nation’s financial system, turning the economy into the overriding issue in the campaign. That led John McCain to cite the turmoil, declare that he was…

The Chicago Connection

It’s surprising that it took this long, but Chicago’s long-standing tradition of public corruption has finally emerged in John McCain’s campaign against Barack Obama.

McCain on Monday unveiled a 30-second TV spot that attempts to link Obama with various players in the city’s enduring history of political sleaziness. The ad begins with a narrator, in a grave voice, announcing that Obama "was born of the corrupt Chicago political machine." It quickly flashes to a clip of Obama defending his personal toughness by saying that he comes from Chicago…

A Midwest Color Line?

In fall 2006, before Barack Obama and his coterie of astute political strategists decided to launch his campaign for president, they burrowed into the polling details of the U.S. Senate race in Tennessee that year.

Why? That was the most recent contest in which race might have played a significant factor in the outcome of a statewide election. Democrat Harold Ford, an African-American Congressman, narrowly lost the Senate race to Bob Corker, a white Republican…