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From Outsider To Politician

By Eli Saslow
Washington Post Staff Writer
Thursday, October 9, 2008

SPRINGFIELD, Ill. The taunting began as soon as Barack Obama joined the Illinois Senate in January 1997. He had expected to face some skepticism as a political neophyte, but not such outright hostility. For the first few months of his career as a lawmaker, Obama navigated the unfamiliar corridors of the state Capitol like a misfit lost in a new school, sometimes complaining to colleagues that he was "getting it from all sides."

He was a Democrat surrounded by Republicans. A Harvard intellectual chided by good old boys. A biracial progressive in an environment rife with racial tension. A sophisticated urbanite living in a town built on cornfields, 200 miles removed from his family in Chicago.

Even those senators who seemed like natural allies treated Obama with nothing but enmity. Rickey Hendon and Donne Trotter, fellow black Democrats from Chicago, dismissed him as cocky, elitist and, Trotter said, "a white man in blackface." When those insults failed to rile him, the two bought a copy of Obama's 1995 autobiography, "Dreams From My Father," and used the book to concoct more. They teased him for smoking marijuana as a teenager and for being raised by his white, Kansas-born grandmother. Most frequently, they ridiculed Obama for his complex ethnicity. You figure out if you're white or black yet, Barack, or still searching?

Obama ignored them. "Give it time," he told friends, "and I'll bring those guys around."

Obama has built a biography on overcoming obstacles -- on fusing unlikely bonds that help him to adapt and then advance. He knew from the moment he took the oath of office in Springfield that he wanted to move beyond the state Senate, so he set out to orchestrate his rise in trademark fashion: by emphasizing relationships over results; by transforming from an outsider into the ultimate insider.

Just as he had before -- as an American child who moved to Indonesia, an Ivy League graduate who worked in housing projects on Chicago's South Side and a black student who enrolled at Harvard Law School -- Obama arrived in Springfield with limited knowledge of his environment and few friends to guide him. He left eight years later with the legislative accomplishments, political savvy and network of allies needed to win a seat in the United States Senate.

Obama declined to be interviewed for this article, but conversations with more than a dozen friends and colleagues portray his time in Springfield as a political baptism performed at warp speed, engineered by Obama's vast self-confidence and ambition.

His legislative record in the state Senate showed promise, but it was fraught with 129 "Present" votes, watered-down bills and a dearth of significant accomplishments -- shortcomings that hardly affected his success. With an eye toward the future, Obama decided to befriend everyone in Springfield who could help him get where he wanted to go. And that included the two men who mercilessly hazed him: Hendon and Trotter.

* * *

It was a daunting task, since Obama's first impression on his colleagues in Springfield was so disastrous. He had won his seat by challenging the validity of opponents' petition signatures, a tactical move that knocked a popular black incumbent named Alice Palmer off the ballot and allowed Obama to run unopposed. During his first week at the state Capitol, he scheduled a meeting with Senate Minority Leader Emil Jones (D) to request a heavy workload and coveted committee assignments. Then Obama invited a few other senators out for beers and indicated, Trotter said, "that he had higher places he wanted to be."

His eagerness vexed fellow Democrats, many of whom either wrote him off or privately encouraged him to slow down. Rather than heed their advice, Obama spoke regularly to the news media about his distaste for the laziness and political gamesmanship of "old politics" in Springfield.

For one of his first major projects as a senator, he sponsored an ethics bill that made it illegal for senators to receive gifts from lobbyists. The successful effort reinforced Obama's public image as a do-good reformer but annoyed some colleagues.

Obama had enjoyed giving interviews to reporters during his tenure as the first black president of the Harvard Law Review, classmates remembered, and legislative sessions provided a forum in which he liked to deliver impassioned arguments in front of his colleagues and the media. He had a mastery of constitutional law and a talent for elegant speaking, assets that served him well as a University of Chicago law professor, where students would listen to his lectures, rapt. But in Springfield, his speeches sometimes played out to a soundtrack of groans or the background chatter of indifference. Colleagues sometimes walked around the room while Obama spoke, and he often sat down discouraged.

Once, at a revenue committee meeting, Obama delayed the proceedings to raise a series of astute questions about committee bylaws. He spoke only a few sentences before a senior colleague interrupted him.

"Hey, enough already," said Denny Jacobs, a Democrat. "Learn on your own damn time, will you? Some of us want to finish this up and get the hell out of here."

"Barack had this misconception that you could change votes with thoughtful questions and good debate," said Jacobs, who has since retired from politics to become a lobbyist. "That was a little idealistic, if you ask me. It's not necessarily about smarts and logic down there. Votes are made with a lot of horse trading, compromise, coercion, working with the other side. Those are things that Barack can do -- can do very well, actually. But it took him a little while to figure it out."

Said Hendon: "Sure, he was smart. But he didn't understand the basics of politics yet. He wasn't a good politician."

Stuck in the legislative minority, Obama had nothing but time to stew over his slow start. Republicans set the schedule, and they left Democrats in the dark about what time each day's session would begin and end. Obama lived at the Renaissance Inn, on the edge of downtown, where the long vistas of farmland from a room on the top floor reinforced the distance between his new life and his family. He watched ESPN. He played basketball each morning at the YMCA. He talked to his wife, Michelle, for almost an hour each night.

After weekends at home in Chicago, Obama sometimes considered leaving late for the legislative session to spend an extra day at home, some of his friends said. He would miss nothing but a few meaningless votes, he reasoned, and he could accomplish more by meeting with constituents in his Hyde Park neighborhood. Friends persuaded him to return to Springfield only when they reminded him of the political ramifications: A lot of missed votes, advisers said, might permanently scar his résumé. He needed to succeed downstate in order to build a record.

"There were times when the politics of Springfield troubled him, but he's not somebody who throws up his hands," said Abner Mikva, a former congressman who mentored Obama in Chicago politics. "He realized he needed to do some things their way, not always his way. He changed his approach. He knows how to adapt and succeed."

Midway through Obama's first term, Jacobs realized that he would be a quick learner. One day Jacobs stopped the new senator in a hallway of the Capitol and pointed out a decorative poster on the wall. It showed how a bill becomes a law in Illinois, and it depicted a chart of steady progress as legislation moved efficiently from one house to the next. Each step was illustrated with bold, black lines. Obama laughed at the simplification.

The chart, he and Jacobs agreed, might be more useful as toilet paper in the men's restroom.

* * *

Obama needed allies to make headway in a place like this, so he set out to find some. A group of Springfield political aides and lobbyists invited him to join their poker game, a low-stakes gathering attended by three other senators. On a weeknight in April 1996, Obama met the other players in a private room at a local country club. Big-screen TVs showed a Chicago Bulls game, and cigar smoke clouded the air.

His arrival surprised the other senators at the table. Jacobs, Terry Link and Larry Walsh -- all white Democrats, all older than 50, all from rural parts of the state -- would become Obama's closest friends in Springfield, but they viewed his initial arrival as the intrusion of an outsider. Jacobs was a loudmouth from the Iowa border, a self-described "backroom dinosaur" famous for his love of gambling. Walsh was a farmer from Elmwood who sometimes snuck out of session for a hot toddy. Link was a forklift business owner who narrowly graduated from high school.

As the young black senator from Chicago -- an Ivy Leaguer, a law professor -- bought into the poker game for $100 and lit a cigarette, Jacobs wondered: "What could he have in common with us?"

"It wasn't the most obvious fit," Jacobs said. "You've got two fat guys, a medium-heavy guy and then Obama. On the surface, there's not a lot that we shared."

Obama folded frequently during the games, preferring to watch the action unfold until he could pounce with the occasional great hand. He filled the long gaps in between by seeking advice from his playing partners about balancing work and family, crafting legislation and aligning with Republicans. Even as Obama routinely took their money, the other players regarded him as naive but genuine. In various capacities, Link, Walsh and Jacobs all considered themselves Obama's mentors.

Obama was never a big drinker, but he faithfully brought along a six-pack of beer and downed a couple. He smoked and pitched in for midnight pizza. The poker game eventually migrated to Link's house and became the one social staple on Obama's schedule. The Committee Meeting, Obama called it -- and the appointment stood for eight years. His poker-mates sometimes teased him for becoming "one of the good ol' boys."

Fitting in, for Obama, had never been a natural process so much as a learned skill -- something that required adjustment and work. At Harvard, he befriended conservatives who eventually helped elect him president of the Law Review. As a young community organizer in Chicago, he emulated the speaking cadence of black pastors and joined Trinity United Church of Christ to help him connect with the city's South Side.

In Springfield, he decided he needed to play golf. Democrats who felt useless in the legislative minority sometimes left the session to play 18 holes in the early afternoon, and their on-course conversations ranged from meaningless trash talk to political dealmaking. Link invited Obama to play and watched the beginner hack his way around the course. Frustrated by his incompetence and worried he might not be invited again, Obama signed up for lessons. He almost beat Link the next year.

After his first year in Springfield, Obama took a golf trip to southern Illinois with his top adviser, Dan Shomon. Obama wanted to test how rural voters would respond to a black man, because he already had designs on a run for statewide office. Shomon coached him: Order regular mustard instead of Dijon; wear simple golf shirts instead of fancy button-downs. Obama returned from the trip convinced he could assimilate.

By the time Obama invited a young incoming senator to visit him in Chicago in the fall of 1997, he already felt like a veteran of Springfield politics, ready to dispense advice. Kimberly Lightford, then 29, visited his office a few months into her campaign for a Senate seat. She had never met Obama, but he already knew much about her. "He basically recounted all the details about my little state Senate race, so I didn't have to tell him anything," Lightford said. "He made me feel pretty important."

He asked Lightford if she had any campaign debt, and she wearily nodded. Obama was earning $49,000 a year as a state senator and routinely borrowed $20 from his poker buddies, but he reached into his desk and pulled out his checkbook. Before Lightford left his office, Obama handed her a $500 donation.

"It was amazing, because he also gave me some advice that I really appreciate to this day," Lightford said. "I was young and idealistic, and he told me: 'You know, when we all get elected we think we're going to go down there and change the world overnight, but that's not going to happen. It's a process. You're going to have to learn the game. You're going to have to make friends. You're going to have to navigate the place if you want to open roads and make things happen.' "

* * *

For Obama, only one road in Springfield remained blocked. Hendon and Trotter, two leaders in the black caucus, had both been in the state Senate for three years before Obama's arrival. They represented two of Chicago's destitute neighborhoods, and they repeatedly accused the newcomer of failing to understand the issues of the inner city. He cared more about his career than his constituents, they said. Hendon once told a newspaper that Obama was so ambitious he would like to run for "president of the world."

Hendon in particular regarded Obama as a foreigner to black Chicago. A lifelong resident of a blighted neighborhood on the city's West Side, Hendon had marched with the Black Panthers and seen his block damaged by the 1968 race riots. He married at 17 and became a grandfather in his mid-30s. He laughed when he imagined Obama as a child in Hawaii, exploring blackness by reading about racial persecution in magazines, watching Julius Erving play basketball or listening to gospel music.

Obama had spent four years organizing residents in the housing projects of Roseland, on Chicago's South Side, but Hendon considered that little more than a surface introduction. "That's a small start," he said. "But to a lot of people from my area, Roseland almost seems nice."

Said Trotter: "There was a sense for many people in Springfield that Barack wasn't black enough. He was just . . . different. It's like being poor when it's 80 degrees and sunny, and you have plenty to eat. Or like being poor when it's 10 degrees and you're just trying to survive. He didn't understand it the same way we did."

Obama tried to dismiss them as jealous -- of his education, his intellect and his budding relationship with Jones, the black Senate minority leader. Obama nominated Lightford as chair of the black caucus, a tactic that helped mitigate Hendon and Trotter's role in his political future. Still, he sometimes left caucus meetings early or called Lightford beforehand to ask if he could skip altogether. "There were a lot of days when he called and said, 'Sorry Kim, but I just don't feel like taking it today,' " Lightford said.

Obama's poker buddies encouraged him to stand up to Hendon and Trotter, but he refused. Not his style, he said. And why sink to their level? When Hendon ridiculed Obama, his standard comeback was a dismissive shrug and a wave of his hand. Ah, Rickey, you've always got something to say."I never would have called him a fighter," Hendon said. "He used the silk gloves, and I used the iron fists."

The tension between the two men peaked on June 11, 2002, after Hendon made an impassioned speech on the Senate floor urging his colleagues to preserve funding for a child welfare facility in his district. It was, Hendon remembers, "basically the most emotional speech of my life, and I was pulling out all the stops." Every Republican still voted against him. Every Democrat voted with him -- except Obama and three other members who made up a faction known in Springfield as "liberal row."

Incensed by those four votes, Hendon walked across the floor and confronted Obama, who explained by saying "something about fiscal responsibility," Hendon recalls. A few minutes later, after Hendon's proposal had lost, Obama stood up and asked to have his previous vote changed to a "Yes" for the record, saying he had misunderstood the legislation. His request was declined, and Hendon stood to criticize Obama for political maneuvering.

Infuriated that Hendon had embarrassed him publicly on the Senate floor, Obama walked over to his rival's seat, witnesses said.

"He leaned over, put his arm on my shoulder real nice and then threatened to kick my ass," Hendon said.

The two men walked out of the chamber into a back room and shoved each other a few times before colleagues broke them apart, Hendon and other witnesses said. Obama and Hendon never talked about the incident with each other again, but they reached an awkward understanding. Hendon stopped teasing Obama; Obama started voting with Hendon more regularly. Hendon now supports Obama for president.

Some of the legislators on the floor that day believed Obama had finally snapped after more than five years of tolerating Hendon's provocations. But Obama's allies, the poker buddies and other friends who knew him best, wondered if his actions resulted from a deeper calculation. Had he actually reacted, so uncharacteristically, out of pure emotion? Or was his scuffle with Hendon a final, brilliant tactic in coalition-building?

"He finally met Rickey on his level, and that got him some respect," Lightford said. "That's what Barack needed to do, and it worked. They didn't tease him so much after that. It was like they finally realized that Barack was more than some soft punk to push around. He could play tough to get his way."

* * *

He could also play smart, and Obama used his relationships with new allies to build his résumé. Shortly after Democrats overtook the Senate in the 2002 elections, Obama approached Jones, the new Senate president, and asked for his assistance.

Obama blamed his loss in a 2000 election for Congress on his perceived lack of political experience, he told friends, and Jones could assist him in filling that gap. He scheduled a meeting with Jones in his office and asked the majority leader to help make him a U.S. senator. Jones, who had grown so close to Obama that he considered him a godson, immediately agreed.

During Obama's final two years in Springfield, Jones gave him coveted committee assignments and several high-profile bills to sponsor, other senators said. Jones sometimes scheduled legislative sessions around Obama's Senate campaign events.

"The big thing the president did was to step in and give Barack a lot of bills where there may have been a bunch of work done on them," Trotter said. "We'd been in the minority for a long time, so a lot of bills had just been sitting there, mostly done but not yet passed. President Jones gave a lot of those to Obama to shepherd through. He might not have to do a lot of work in some of those situations, but he could get a lot of credit."

Obama fulfilled his end of the deal by adapting the cool demeanor of a power broker. Gone was the verbose young senator who liked to hear himself talk on the chamber's floor. Toward the end of his time in Springfield, Obama became one of the quietest senators, colleagues said. He spoke only on big-ticket issues and delivered his thoughts with cadence and brevity. When he stood, the room now fell silent.

Listening, Obama decided, was usually more persuasive than lecturing. He offered to hear Republicans' ideas before they proposed them on the floor, acting as an early barometer of Democratic response. Even though his record leaned more liberal than most senators', Obama voted with Republicans during his eight years in the Senate more frequently than all but a few other Democrats. Occasionally, he offered to speak on behalf of legislation proposed by Republicans.

One longtime conservative, Republican state Sen. Kirk Dillard, cut a commercial for Obama's presidential campaign last year, saying, "Obama worked on some of the deepest issues we had, and he was successful in a bipartisan way."

In an interview during his Senate years, Obama listed his idols as Mahatma Gandhi, Abraham Lincoln and the Rev. Martin Luther King Jr., prompting one colleague to joke, "Bold choices, huh?" Similarly, as a legislator, Obama molded his ideas until few reasonable people could disagree, becoming an expert at building consensus. His aspirations for universal health care resulted in a more modest expansion of Illinois's current system. He took control of a once-controversial bill requiring police to videotape interrogations and tinkered with it until it passed without a single dissenting vote.

"He realized sometimes that you can't get the whole hog, so you take the ham sandwich," said Jacobs, one of Obama's poker buddies. "For somebody who people criticize for being an idealist, I've seen Barack get realistic pretty fast. He understands that it's better to accomplish what you can, take your lumps and move on."

Jones helped Obama become the chief sponsor of a racial profiling bill that colleagues in the black caucus had developed. Hendon, who said he had worked on the legislation for a few months, proposed that police officers be punished and even fired for targeting minorities. In his early arguments for the bill, Hendon told first-person stories about the humiliation of being pulled over with his wife in the car and forced to stand in the rain. The bill did not gain significant support.

Then Obama took charge of the legislation and met with conservative Democrats and some Republicans. Taking their suggestions, he amended the bill so that it required police departments to keep track of whom officers pulled over. Those officers who showed patterns of racial profiling would receive warnings and counseling. On the Senate floor, Obama argued that the legislation was an essentially an insurance issue meant to help Illinois ward off lawsuits. Some police organizations supported his version of the bill, and it passed with ease.

During his two years in the majority, Obama worked his name onto 200 bills that became laws. He served as the primary sponsor on more than 20 successful measures. "I remember more than a few days," Trotter said, "when almost everything we voted on had his name on it."

By the time Obama readied for his 2004 campaign for U.S. Senate, he could run on a record of proof as much as promise. He had built a résumé that showed a prolific legislator, and a reformer who stayed true to liberal principles.

There remained only one problem with Obama's résumé, a rare hole the politician himself had never foreseen, friends said. Obama voted "Present" 129 times in the state Senate, all during his six years in the minority. His political opponents have used those votes as proof of cowardice. By refusing to vote "Yes" or "No," they argue, Obama avoided casting votes on controversial issues in order to protect his record.

But Obama placed more than half of his "Present" votes along with other Democrats in organized protest of Republican legislation, voting records showed. Allies said many of his other "Present" votes reflected his tendency toward analysis and precision: He voted "Present" whenever he liked a bill but felt uncomfortable with its wording, they said.

"Nobody ever thought the 'Present' votes would become an issue," Lightford said. "Obviously, he never thought so, or he probably would have voted 'Yes' or 'No.' "

Obama won the Democratic primary for U.S. Senate and delivered a speech at the 2004 Democratic National Convention that turned him into an overnight celebrity, and he returned to Springfield with swagger, colleagues said. In conversations with allies -- at the poker game or on the golf course -- he spoke excitedly about Washington, his next destination.

Sure, he looked forward to a chance to effect significant legislative change, he said. But he also told friends that he relished the challenges at "the next level." There, he would find new secrets to unlock, new coalitions to build and new games to play.

Again, Obama felt confident he could win acceptance.

"You could tell he couldn't wait to move on to Washington," Lightford said. "He wore it well. It was kind of like: 'Yeah, I can do Springfield with my eyes closed. What's next?' "

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