Surviving political boot camp
Obama had a beat-up Honda and a city map to navigate the streets as a community organizer on the South Side, a cluster of poor neighborhoods ravaged by the loss of steel mills and factory jobs.
Working for the Developing Communities Project, Obama met with black pastors and tried to mobilize people to agitate for themselves — whether it was lobbying for a job training center or cleaning up public housing.
He quickly won over skeptics, says Loretta Augustine-Herron, one of the project founders.
“He looked so young and tender” and the ladies soon dubbed him “babyface Obama,” she recalls. “But he was very businesslike, very respectful. He had incredible people skills. He would keep us on task to move us along, to make things happen. If we’d get distracted, he’d shake his head and say, ‘Come on guys. This is important.’”
She says Obama also offered sensible advice: “He would talk about no permanent friends, no permanent enemies. He would say, ‘Don’t get personalities involved.’”
Obama — who calls his organizing work “the best education I ever had” — gradually became a skilled conciliator, says Gerald Kellman, the man who hired him.
“He became very effective at getting people who initially did not get along … to work together and build alliances,” Kellman says. “He found a way to be tough and challenging when he didn’t like something. At the same time, he was not one to burn his bridges.”
Chicago became the place where Obama set down roots.
He joined the Trinity United Church of Christ and became friends with its pastor, the Rev. Jeremiah Wright, whose incendiary comments about race and America would later raise questions about Obama’s judgment and threaten to derail his presidential campaign. Obama denounced the remarks after they created a national uproar; he no longer attends the church.
Chicago was also Obama’s political boot camp, where he learned about the power of coalitions and the importance of making connections.
But Obama was not all work. He wrote short fictional stories that evocatively captured the feel of the streets. (He would later write two best-selling books, one of them a memoir.)
Obama also remained close to his family. Soetoro-Ng, who is nine years younger, recalls how he “really took on the role of a father” after her own father died. He escorted her on college tours, introduced her to jazz, blues and classical music — and, much later, consoled her when their mother died of ovarian cancer at age 53.
After three years as an organizer, Obama had become increasingly pragmatic about what he could accomplish.
“The victories were small: they changed peoples’ lives, but they didn’t change American society, and he wanted to do that,” Kellman says.
Obama took a giant leap from the gritty South Side to the heady atmosphere of Harvard Law School, the training ground for America’s elite. He made history as the first black president of the Harvard Law Review, perhaps the most prestigious law journal in the nation.
The distinction brought a flood of publicity. In an interview with the Los Angeles Times, Obama said a Harvard education “means you can take risks. You can try to do things to improve society and still land on your feet.”
After his first year, Obama worked one summer at a corporate law firm in Chicago, where his adviser was Michelle Robinson, another Harvard law graduate and a product of a working-class family.
They later married and had two daughters, Malia, now 10, and Sasha, 7.
As Obama prepared to leave Harvard, job offers poured in.
But he already had a plan. He would return to Chicago for a political career.
‘A complete political talent’
Again, he chose a grassroots job. Obama ran a voter registration drive that added tens of thousands to the rolls.
“He was very straightforward and had a no-nonsense, all-the-cards-on-the-table approach,” recalls Sandy Newman, founder of the national group Project Vote!
Obama also began carefully mapping out a path that positioned him for public office.
He joined a small, politically connected boutique law firm that did civil rights litigation. He and Michelle lived in Hyde Park, the racially mixed neighborhood around the University of Chicago that is home to progressive politics, intellectuals and a sprinkling of Nobel Prize winners.
“He moved in an area where an independent can come out of nowhere to win,” says Don Rose, a veteran political strategist. “By choosing to work at [that law firm], he was making a political statement to where he stood.”
He made many acquaintances in Hyde Park, but none proved more troublesome during the campaign than Bill Ayers, a college professor who was co-founder of the Weather Underground, an anti-Vietnam war group that claimed responsibility for bombing government buildings.
The two men served on the boards of two civic organizations in Chicago, and Ayers hosted a meet-the-candidate session during Obama’s first legislative race. That connection has prompted repeated attacks from Republicans who claim it demonstrates flaws in Obama’s character.
By all accounts, the two men are not close, and Obama — who was 8 when Ayers was protesting — has condemned his radical past.
Obama has also been dogged by another association, this one with real estate developer Antoin “Tony” Rezko, who raised funds for many Illinois politicians, including the senator. Rezko was recently convicted of using his influence with the administration of Gov. Rod Blagojevich to launch a $7 million fraud and extortion scheme.
Obama was accused of no wrongdoing and was barely mentioned in the trial, but the connection has proven an embarrassment. Obama gave about $159,000 from Rezko-related contributions to charity.
On the more positive side, Obama also impressed a wide number of influential Democrats and party donors who have proved invaluable in his campaigns. Among them is Abner Mikva, a former Illinois congressman and federal judge.
“He’s just a complete political talent,” says Mikva, who became a mentor. “He likes to get along with people. He likes to listen to them … He has these great talents and skills to build coalitions.”
Obama’s friendship with Mikva also illustrates the next president’s knack for making the right connections.
“If you don’t like the guy, he’s a calculating politician,” says Rose, the political strategist. “If you do, he’s a smart, methodical worker. He does nothing that’s different from most politicians, even the reform politicians. The difference is he’s extraordinarily gifted … His greatest capability is he never makes the same mistake twice.”
But that skill was nothing without a political opportunity. While waiting for one, Obama became a lecturer at the University of Chicago Law School. He taught constitutional law and was popular with students and faculty, though some found him a bit remote.
“He’s a great conversationalist and a good listener,” says Richard Epstein, a law school professor who was not a close friend. “But he never tips his hand to what he thinks … At the end of the day, you don’t know whether you’ve changed his mind or not.”
In 1996, when Obama was elected to the state Senate, some lawmakers dismissed him as an ivory-tower liberal.
“Some members of both parties thought that Barack was longwinded and a tad aloof and arrogant. Not me,” says state Sen. Kirk Dillard, a Republican and Obama friend.
Obama won over many colleagues in nearly eight years in Springfield, joining them for weekly poker games, befriending suburban and white rural legislators.
“He was very inquisitive,” says former state Sen. Denny Jacobs, a poker buddy. “He wanted to know why. He would ask a lot of questions, even on the floor (of the Senate). I’d say, ‘Barack, enough is enough. How much more do you need?’”
Obama had several legislative successes after his party took control of the Senate. He passed measures that limited lobbyists’ gifts to politicians; helped expand health care to poor children; and changed laws governing racial profiling, the death penalty and the interrogation of murder suspects.
He generally was a liberal, but he reached across party lines to work with Republicans.
“Barack can compromise without giving up his principles,” says Dillard, a McCain supporter. “He’s a realist and he knows when to fold his cards.”
Obama stumbled badly, though, in 2000 when he challenged U.S. Rep. Bobby Rush, a former Black Panther member with deep roots in the community. Obama was dogged by the question raised by some pundits and black politicians — whether he was “black enough” for the district.
Obama says there never has been any question about his being black. He addressed the race issue in his book “The Audacity of Hope,” describing slights and prejudices he has encountered.
“I know what it’s like to have people tell me I can’t do something because of my color, and I know the bitter swill of swallowed-back anger,” he wrote.
But in that congressional contest, Obama was seen as the outsider. Rush, the insider, crushed him in the primary.
Two years later, Obama eyed another office: U.S. Senate.
Valerie Jarrett, his friend, was leery, telling him: “‘My gosh, you can’t lose two races in a row. You’ll be done in politics.’ He said, ‘If it’s OK with me, it should be OK with you. I’m not afraid of losing.’”
Obama won a crowded primary and quickly emerged as a rising star, impressing Democratic presidential nominee John Kerry, who tapped him for the keynote speech at the 2004 convention.
In 17 minutes, Obama jumped from an obscure state lawmaker to a force in national politics.
That fall, Obama, profiting from some lucky breaks, won his U.S. Senate seat in a landslide. Almost immediately, talk began of a presidential run.
Journey’s end
In 22 months on the campaign trail, Obama has walked a fine line, presenting himself to America as a fresh face and an outsider — but one with the knowledge and mettle needed for the White House.
He has rallied huge crowds with inspiring words and vows to bring change to the calcified ways of Washington, even as critics have tried to cast him as a celebrity whose oratorical sizzle conceals a thin resume.
But in a series of debates — including three with McCain — Obama proved adept and skilled at answering questions and offering proposals about health care, the financial bailout and Iraq, among other issues.
And his approach to dealing with the Wall Street meltdown earned a much ballyhooed endorsement from Colin Powell, the former chairman of the Joint Chiefs of Staff, who praised Obama’s “steadiness … [and] depth of knowledge.”
Throughout his campaign, Obama has talked about defining moments — from his victory in Iowa to the day five grueling months and 53 contests later when he won enough delegates to claim the Democratic nomination.
On that June night, as well as this Tuesday, he made history.
(Associated Press)
