I got my first sight of Obama in December 1999, at a church in the Bronzeville neighborhood, on the South Side of Chicago. As a correspondent for the "Chicago Reader," I'd been assigned to go check out this young state senator who thought he could beat Rep. Bobby Rush. It was a Saturday afternoon -- as a greenhorn challenger, Obama wasn't getting the Sunday pulpit invitations -- and maybe a dozen people were scattered in the worn pews. Obama was a mere two-term state senator, and this was half a decade before "-mania" was added to his name.
"The first thing people ask me is, 'How did you get that name, Obama,' although they don't always pronounce it right. Some people say 'Alabama,' some people say 'Yo Mama.' I got my name from Kenya, which is where my father's from, and I got my accent from Kansas, which is where my mother's from."
At the time, Obama was teaching constitutional law at the University of Chicago, and this was the sort of awkward, beginning-of-the-semester joke you hear from a professor trying too hard to prove a sense of humor. He went on to give a stilted speech attacking Rush as "reactive."
Obama lost that election, in humiliating fashion. He got only 31 percent of the vote, and had to endure charges that he was a "white man in blackface" -- an alien to the black community whose main supporters were wealthy white liberals funding an "Obama project" to push him up the political ladder.
Four years later, when I went to interview him about his U.S. Senate campaign, I saw a different Obama. "Good to see you again," he intoned, casually, gliding across the room like Fred Astaire playing Abe Lincoln. We went into his office, where, sitting under a giant photo of Muhammad Ali knocking out Sonny Liston, Obama tried out some lines he would use at the Democratic National Convention.
"There is a tradition of politics that says we are all connected," he said. "If there is a child on the South Side who cannot read, it makes a difference in my life, even if it's not my child. If there's an Arab-American family who's being rounded up by John Ashcroft without benefit of due process, that threatens my civil liberties. Black folks, white folks, gay, straight, Asian -- the reason we can share this space is that we have a mutual regard. That's what this country's about: e pluribus unum. Out of many, one."
That was the mission statement of 21st-century Obama. As a black candidate, he'd been too inhibited, too embarrassed, to force out phrases like "our community." Finally, he was comfortable in his own skin, now that he'd accepted that the skin was half-white. And his defeat had matured him. Realizing he'd gone as far as he could by telling people he'd been president of the Harvard Law Review, he'd returned to Springfield and built a serious record as a legislator.
My new book, "Young Mr. Obama: Chicago and the Making of a Black President," tells the story of how Obama found his voice as a politician, and why he couldn't have found it anywhere but his adopted hometown. The book actually begins in 1985, when Obama arrived in Chicago as a 23-year-old community organizer. For the first time, you can read interviews with all three "Obama Mamas" -- the women of the Developing Communities Project, depicted in "Dreams From My Father" as Angela, Mona and Shirley. You can also read about how Obama used Alinsky-style tactics to force the Chicago Housing Authority to clean up asbestos in the projects. In those early years, Obama was an Ivy League graduate searching for his identity as a black man, and he consciously chose the South Side of Chicago, the largest concentration of African-Americans in the nation. It also helped that Chicago had just elected its first black mayor, Harold Washington, who would become Obama's political idol. When he first began plotting a career in politics, Obama wanted to be mayor of Chicago, not president of the United States.
Obama spent only three years as a community organizer, leaving for Harvard Law School in 1988. When he returned to Chicago, he began one of the great social climbs in American history, charming a succession of mentors who would aid his political rise: Judge Abner Mikva, the former White House counsel; Emil Jones, president of the Illinois State Senate; and David Axelrod, the political consultant who left his first meeting with Obama convinced that he'd found the next John F. Kennedy.
Obama also learned to play politics the Chicago Way. In his first campaign for office, he knocked his mentor, state Sen. Alice Palmer, off the ballot by challenging her petitions. Palmer felt she'd been stabbed in the back, and never forgave Obama, even campaigning for Hillary Clinton in 2008.
Above all, the book explains why Obama's rise could not have taken place anywhere but Chicago, which has a longer history of black political empowerment than place in the nation. The relationship between Obama and Chicago was the perfect match of a man and a city. Black Chicago had elected a mayor and a senator. In Obama, it found a politician it could lift to the highest office of all. In the words of Al Kindle, one of Obama's early political aides, "We were looking for someone to do it, and he was looking for a place to do it in."
Edward McClellan's book, "Young Mr. Obama: Chicago And The Making Of A Black President," can be ordered here.
Every Friday, HuffPost's Culture Shift newsletter helps you figure out which books you should read, art you should check out, movies you should watch and music should listen to. Learn more