I am surprised at how many elected officials—even the good ones—spend so much time talking about the mechanics of politics and not matters of substance. They have this poker chip mentality, this overriding interest in retaining their seats or in moving their careers forward. . . .
—BARACK OBAMA
Barack Obama’s first foray into electoral politics revealed both the burning intensity of his personal ambition and his deeply held desire to press for social change, particularly in poor African-American communities. To Obama, it displayed once again the thorny thicket of intramural politics that besets Chicago’s black community. The city’s African-American political universe is lighted by a select group of insiders who have amassed power and prestige, and they are loath to relinquish it. It is also a society of unyielding internal rancor, which often impedes overall black progress. For these reasons, as Obama entered the public political sphere, the eternal optimist began to express pessimism about the state of black Chicago.
“Upon my return to Chicago,” he wrote in Dreams from My Father, which was published around this period, in 1995, “I would find the signs of decay accelerated throughout the South Side—the neighborhoods shabbier, the children edgier and less restrained, more middle-class families heading out to the suburbs, the jails bursting with glowering youth, my brothers without prospects. All too rarely do I hear people asking just what it is that we’ve done to make so many children’s hearts so hard, or what collectively we might do to right their moral compass—what values we must live by. Instead I see us doing what we’ve always done—pretending that these children are somehow not our own.”
Running Project Vote and working for Judson Miner provided Obama with entree to the diverse constellation of black politicos on Chicago’s South Side. So when an opportunity to run for public office presented itself in 1995, Obama seized it. A respected state senator in her first full term, Alice Palmer, had decided to run for Congress, which led to Obama cutting his first deal to advance his career in politics. Palmer was a progressive African American in the vein of Obama, and she threw her support behind Obama as her replacement.
But that is only where the story begins.
In Obama’s version of events, Palmer agreed that even if she was not successful in the three-person race for Congress, she would retire from politics and he would run for her seat. But when Palmer began to falter badly in the congressional contest, she changed course dramatically. Her supporters met with Obama and asked him if he would step aside if Palmer was to lose. This would allow her to run again for the Illinois Senate seat she was holding, but it would leave Obama out in the cold. After pulling together a campaign, Obama had no interest in ditching the effort. And he did not equivocate in expressing that sentiment to Palmer’s representatives. At thirty-four, Obama was eager for this next step in his evolution. This was, after all, a man who had mused to his brother-in-law a couple of years earlier that, hey, you never know, he might be the president of the country one day. Palmer, in Obama’s view, was reneging on an agreement that they had negotiated in good faith. So he told Palmer’s people that she had promised to relinquish her seat and support him, and that he would not withdraw from the race.
Predictably, this did not sit well with Palmer. She, indeed, lost the congressional primary contest in November 2005 to Jesse Jackson Jr., and then quickly filed to run for her old seat in the March 2006 Democratic primary against Obama—even though she had publicly supported him for the seat. “Since she endorsed me, I can always use, ‘Even my opponent wants me’ as a campaign slogan,” Obama quipped to the Chicago Tribune.
But humor aside, this established a problematic election for the upstart Obama. Suddenly, instead of running at the head of the pack with the incumbent’s blessing, he was running against the incumbent herself. He had worked the hustings and accumulated a great deal of support for his candidacy, but he would have been hard pressed to match Palmer’s power of incumbency: a ready-made army of supporters to distribute literature and get people to the polls on election day, as well as the endorsement of an array of established black politicians. Indeed, Palmer called a press conference and accepted a petition from more than one hundred supporters urging her to seek reelection. Also in her corner was the new congressman, Jesse Jackson Jr. In fact, fresh from the congressional victory, Jackson’s field organizer attended Palmer’s press conference and pledged full assistance. Palmer also possessed an incumbent’s most potent weapon—name recognition from her previous election—while Obama’s name was not a plus to his campaign. When it came to his name, the debate generally revolved around which was odder—his first name or his last.
But Obama had one card up his sleeve. He could not envision how Palmer’s supporters, even as solidified as they seemed to be, had gathered the necessary number of voter signatures on her nominating petitions in such a short time. Palmer herself confessed at her press conference that the nearly sixteen hundred petitions she had filed with the state elections board had been accumulated in just ten days. So a volunteer for Obama challenged the legality of her petitions, as well as the legality of petitions from several other candidates in the race. As an elections board hearing on the petitions neared, Palmer realized that Obama had called her hand, and she acknowledged that she had not properly acquired the necessary number of signatures. Many of the voters had printed their names, rather than signing them as the law required. Palmer said she was desperately trying to get affidavits from those who had printed their names, but time was running out. She had no choice but to withdraw from the race. The other opponents were also knocked off the ballot, leaving Obama running unopposed in the primary.
Publicly, Palmer claimed she held no grudges; privately, she was extremely bitter. This turn of events was embarrassing to her, especially after her poor showing in the congressional contest. But more important than embarrassment, it effectively ended her once promising political career. So she refused to support Obama in the primary or the fall election, telling a Chicago journalist, “I’ve since discovered that he’s not as progressive as I first thought.” Nevertheless, since the Republican Party is almost nonexistent in African-American districts on the South and West Sides of the city, Obama cruised to victory in the fall election.
For Obama, the saga pointed up several things. Rather than winning a position in the Illinois General Assembly by ousting an incumbent or taking an open seat, he appeared to have slipped in the back door on a technicality. And by challenging Palmer, who was highly regarded in black political circles as a fighting progressive, he had left a bad taste in the mouths of many black political leaders, influential people whom he would have to work with in the state capitol and in his district. Palmer, for her part, seemed more than happy to see this bitterness and resentment toward Obama spread to as many people as possible.
But most significantly, the whole episode showed that Obama was an extraordinarily ambitious young man willing to do whatever it took to advance not only his agenda of community empowerment but his own political career.
* * *
OBAMA’S STATE SENATE DISTRICT ON CHICAGO’S SOUTH SIDE WAS one of the most economically diverse in the state. It included some of the poorest African-American neighborhoods and public housing projects in the country, but it was also home to middle- and upper-middle-class residents, most living in Hyde Park. In addition, his district ran up into the South Loop area, just south of the main downtown commercial district of the city. As development spread outward from the city’s high-rises from the 1980s through today, the South Loop and neighborhoods to its near south experienced intense development pressures. The South Loop was undergoing gentrification, with new condominium buildings and town-house communities drawing downtown professionals and others back to city living. Attendant stores, businesses and restaurants sprouted alongside these developments.
Obama’s fratricidal state senate race provided some inside-page grist for the Chicago media, but it was still a relatively obscure contest in a city filled with higher-stakes political intrigue. Yet the emergence of Obama onto the city’s political scene did not go completely unnoticed. Obama’s Harvard pedigree, the release of his first memoir and his own personal eloquence combined to draw some interest from the press and from influential people outside the South Side environment.
He was named one of the city’s top movers and shakers by N’DIGO magazine, a publication tailored to black professionals in Chicago. But the most substantial interest came in the form of a long front-page profile in the city’s leading weekly alternative newspaper, the Chicago Reader. The four-thousand-word article was highly laudatory of Obama, and the last third of the piece was largely an account in Obama’s own words of his views on the complicated intersection of race and politics. The article served as a manifesto of sorts for Obama. This was the first time he was able to voice his political philosophy to the broader Chicago community, especially the all-important liberal set. His vision for a “new kind of politics” was still in its nascent stage, and he was speaking primarily to the more narrow concerns of his future black South Side constituents. But the overall principle was essentially identical to what he preaches politically today: If America is to progress as a free society, people must learn to work together to build healthy communities rather than fight with each other over parochial, self-serving interests. As Obama put it:
The political debate is now so skewed, so limited, so distorted. People are hungry for community; they miss it. They are hungry for change. What if a politician were to see his job as that of an organizer, as part teacher and part advocate, one who does not sell voters short but who educates them about the real choices before them? As an elected public official, for instance, I could bring church and community leaders together easier than I could as a community organizer or lawyer. We would come together to form concrete economic development strategies, take advantage of existing laws and structures, and create bridges and bonds within all sectors of the community. We must form grass-root structures that would hold me and other elected officials more accountable for their actions. The right wing, the Christian right, has done a good job of building these organizations of accountability, much better than the left or progressive forces have. But it’s always easier to organize around intolerance, narrow-mindedness, and false nostalgia. And they also have hijacked the higher moral ground with this language of family values and moral responsibility. Now we have to take this same language—these same values that are encouraged within our families—of looking out for one another, of sharing, of sacrificing for each other—and apply them to a larger society. Let’s talk about creating a society, not just individual families, based on these values. Right now we have a society that talks about the irresponsibility of teens getting pregnant, not the irresponsibility of a society that fails to educate them to aspire for more. . . . I am surprised at how many elected officials—even the good ones—spend so much time talking about the mechanics of politics and not matters of substance. They have this poker chip mentality, this overriding interest in retaining their seats or in moving their careers forward, and the business and game of politics, the political horse race, is all they talk about. Even those who are on the same page as me on the issues never seem to want to talk about them. Politics is regarded as little more than a career.
One of Obama’s central themes was the powerful potential of multiculturalism in American society. Rather than continually fighting white interests and castigating whites for an oppressive history of mistreating blacks, Obama suggested, blacks would do better if they infiltrated the mainstream power structure and worked from there to effect social change.
“Any solution to our unemployment catastrophe must arise from us working creatively within a multicultural, interdependent, and international economy,” Obama said. “Any African Americans who are only talking about racism as a barrier to our success are seriously misled if they don’t also come to grips with the larger economic forces that are creating economic insecurity for all workers—whites, Latinos, and Asians.”
At Harvard, Obama’s practice of patiently listening to all sides of a debate made him popular and defused conflict with members of the school’s conservative ranks. But his steadfast beliefs about multiculturalism and race made him less than a unifying force in Chicago’s black community. The idea of building bridges to people of all races was anathema to many old-school black leaders and so-called black nationalists who still sounded a voice in Chicago’s African-American community. These individuals practiced a form of identity politics. They were not only pessimistic about the capacity of whites to share economic wealth with minority groups, but they were especially wary of blacks like Obama who were educated in elite white institutions, had assimilated into mainstream white society and now espoused these kinds of multicultural notions. It did not help Obama’s cause in these circles that, in addition to his law practice, he was lecturing in constitutional law at the University of Chicago School of Law. The university was situated in Hyde Park, and to some South Side blacks the campus represented the encroachment of the white establishment into what had historically been claimed as African-American turf. The school was considered a physically forbidding and intellectually impenetrable institution of white elitism sitting in the middle of struggling black communities—and there was Harvard Law–trained Obama, teaching classes at this establishment.
Most of this grumbling occurred behind the scenes, although some was aired in public. An African-American political science professor at Northwestern University criticized Obama for his “vacuous-to-repressive neo-liberal politics.” The head of a task force on black empowerment was more direct and more cynical, charging that Obama was little more than a tool of forces beyond the black community. These kinds of concerns from blacks were nothing new to Obama, of course. He had rankled some African Americans at Harvard for trying to promote harmony among partisans by appointing conservatives to editorial posts at the expense of pushing specific blacks up the ladder.
SOME OF THESE ISSUES IN THE BLACK COMMUNITY FOLLOWED Obama into the Illinois General Assembly, where he received a cool reception from some members of the Illinois Legislative Black Caucus. This group of black lawmakers was not immune from internal squabbling. Chicago has two significant communities of African Americans—West Siders and South Siders—and legislators representing districts from each part of town were often at odds, in part because they were competing in Springfield for the same state resources. And Obama did not necessarily ingratiate himself with the legislators by making some privately disparaging comments about the disorganized, free-for-all atmosphere in Springfield. While some lawmakers acknowledged that Obama’s criticisms were on the mark, others wondered, Just who is this hotshot new guy from Harvard Law who shows up in Springfield and immediately takes potshots at us? “At the swearing-in, there was already some heat from certain people,” a Springfield politico recalled.
In fact, the man who soon became Obama’s chief political adviser acknowledged that he did not care for Obama upon their first meeting. Dan Shomon was a hardworking, gregarious, bespectacled wire service reporter who had left journalism to become an aide to Democrats in the state capital. By 1997, Shomon had worked in Democratic Party politics in Springfield for eight years and he knew the terrain. Obama was displeased about the amount of time that his assigned aide was devoting to his staff work and noticed that Shomon was a dogged worker for the senator in the office next door. So Obama pressed the Black Caucus leader, Emil Jones Jr., to have Shomon assigned to him, as well.
Shomon was initially reluctant because he had heard some of the scuttlebutt about Obama. He had also met Obama a couple of times the year before when Obama helped campaign door-to-door for other Democratic legislative candidates. On one of his volunteer walking efforts, Obama ran into another volunteer apparently assigned to walk the same precinct and grew miffed because he felt his time had been wasted. This gave Shomon the impression that Obama could be rather testy and elitist. So when Shomon was approached about working for Obama, his first reaction was: “I am thinking that I am really busy. He wants to change the world and that is great, but I don’t really like the guy that much.” Still, Shomon agreed to meet with Obama, and when Obama took Shomon out for dinner, the two wound up hitting it off. So Shomon went to work for Obama, mostly in the capacity of helping the freshman lawmaker with legislative strategy. Shomon offered to help with media affairs, since that was his specialty as a former reporter. But Obama told Shomon that he did not need a press aide because he dealt with reporters on his own. Obama wanted full control over his own public message, and he didn’t want a spokesperson interpreting his language and ideas.
(Thus began Obama’s cordial, but not chummy, relationship with the news media. He was known for an occasional thoughtful quote, but capitol reporters were not so charmed by him that they consistently sought him out. Obama joked in later years that only one reporter, Dave McKinney of the Chicago Sun-Times, paid him any attention at all. “And McKinney only talked to me to be nice,” Obama said.)
One of Shomon’s first tactical moves would later prove pivotal in pushing forward Obama’s budding political career—and it would convince Obama that he could win a statewide political contest. Shomon told Obama that, because he would be voting on issues that affected Illinoisians outside the Chicago region, he should consider traveling to the southern reaches of the state to gain an understanding of Illinois’s vastly divergent cultures. Obama thought the trip would be instructive for that reason and for another: Springfield was not his final political destination. He harbored notions of running for statewide office one day. This was 1997, before Obama’s first child was born, and there were fewer encumbrances on his time. So, according to Shomon, Obama responded without hesitation: “Let’s do it.” (In Obama’s second book, The Audacity of Hope: Thoughts on Reclaiming the American Dream, he takes credit for the idea of this first far downstate trip.)
Behind Shomon’s thinking was this: Illinois suffers from a constant geographic tussle between the Chicago region and the rest of the state. About two-thirds of the state’s population lives in the Chicago area, which, at roughly eight million people, is the third-largest metropolitan region in the United States, behind New York City and Los Angeles. The remaining third live in rural and small urban communities across Illinois, and these communities consistently complain that they are overwhelmed by Chicago and its collar counties, especially when resources are divvied up by lawmakers in Springfield. Because of this dynamic, most politicians from Chicago are viewed with some suspicion by voters in Chicago’s immediately surrounding suburbs and with even greater suspicion outside the metro region altogether.
But in central and southern Illinois, another factor might play a role in how Obama would be considered: race. Obama was not only a Chicago politician but an African-American one. This was potentially a second strike against him in this part of the world. Southern Illinois, in particular, more resembled the Deep South than the Midwest. It had endured a long history of racial intolerance. At Illinois’s southern tip, where the Ohio and the Mississippi rivers meet, the small town of Cairo has a particularly unsettling past that includes the public lynching of black men in the early 1900s and a race riot in 1967. The riot was so ugly that it helped to spur the departure of thousands of residents. On several trips into this potentially hostile environment, Obama would not only measure his overall reception but also seek to make political and fundraising contacts. The key question: Had the racial equation changed enough that he would be viewed as a friend or, at the very least, a nonthreatening outsider? “I said that we will go for a week and play golf and we will see the state,” Shomon recalled.
On this first trip, Obama’s eyes were opened to this largely white part of the world—the so-called red state world. The two men disagreed over some logistical and political aspects of the trip, but overall it was a resounding success, signaling to both of them that Obama probably could compete in that rural, small-town environment. Obama may have written four hundred serious pages in Dreams about the painful odyssey of finding comfort with his mixed racial ancestry, but he seemed comfortable with his identity by this time.
“We are driving through Perry Township and we pass the Pinckneyville Coon Club,” Shomon recalled, spelling out the word “C-O-O-N” for special emphasis. (Coon in this case was a truncated colloquialism for raccoon, but historically in the United States it has been used as an epithet for a black person.) “And, you know, this guy has never really been in the South. So Barack looks at the sign, and looks at me, and he says, ‘I don’t think they’re going to let me join the Pinckneyville Coon Club.’ He then starts laughing and he is laughing so hard he almost fell off his chair.”
While traveling in another small town on a later trip, Obama and Shomon were pulled over by a police officer in DuQuoin County when they inadvertently turned the wrong direction down a one-way street. When the officer questioned the state license plate on Obama’s green Jeep Cherokee and Shomon told him that Obama was a state senator, the officer “looked flabbergasted,” Shomon said. “He’s not a state senator from these parts!” the officer told Shomon.
Still, in setting after setting on these downstate trips, Obama discovered that everyday people reacted warmly to him. In some cases he was treated like a dignitary because people were not accustomed to a state senator visiting them. “It was just a great trip because it really did open Barack’s eyes,” Shomon said. “He thinks these people are really cool, and they could relate to him—although, you know, they couldn’t pronounce his name.”
The trips were also helpful in yet another regard, allowing Shomon to school Obama in another lesson of politics: Try to adapt as best you can to the culture you are stepping into. Obama did not always take well to Shomon’s unsolicited advice. While Obama’s family never had a great deal of money, his private schooling and Harvard degree meant that he had been immersed in an elite culture, especially during his adult years. One morning, Shomon met Obama coming out of their hotel and noticed that Obama was wearing khaki pants and a silky black shirt with a flat collar and buttons all down the front, a shirt more typically worn to a picnic than to a round of golf. Most significantly, it was not the universal golf uniform of a two- or three-button polo shirt. (Obama shows his minimalistic tendencies by consistently wearing khaki pants and black shirts in casual settings. “Buy him a black shirt for Christmas and he is a happy man. He’s not flashy. That’s all he wears,” his wife once told me.) “So I asked him what was going on with the shirt? And he asked what I meant,” Shomon said. “I told him that we have the golf outing today. He didn’t think anything was wrong with the shirt. I told him that he needed to wear a golf shirt like everyone else. And he asked me why, because he only had one golf shirt and he had worn it playing golf the day before. I said, ‘Well then, wear it again.’ So he put it back on. I reminded him that this was southern Illinois and you don’t want to look too ‘uptown.’ He got mad and kind of frustrated about that. He didn’t have a problem with changing after I explained it to him, but he really had not been exposed to that stuff. He is fairly sophisticated.”
Obama recounted a slightly different version of this anecdote in his second book. He wrote that Shomon told him to wear polo shirts and khakis throughout the trip, in order to fit in. Obama also recalled the story of Shomon advising him in a downstate restaurant to eat regular yellow mustard rather than the more pretentious Dijon mustard. Obama portrays Shomon’s advice as rather petty. These disagreements might appear insignificant on the surface, but they reveal something about each man. Both could be stubborn and opinionated, but each also had legitimate points. And the discussion itself crystallizes a dilemma that political aides have consistently had with Obama: his occasional air of elitism coupled with his skin color. Rightly or wrongly, Shomon was concerned that Obama’s urbane sophistication, coming as it did from a black man, would alienate working-class white voters—and Shomon sought to temper that image. Obama, however, was wise enough to know that if he tried to morph into something that he was not, he would be perceived as inauthentic.
In any case, Shomon and Obama would take more of these trips downstate, and the excursions satisfied Obama that he could win votes among this electorate. These mostly white, middle-class, down-to-earth midwestern people reminded him of his grandparents and he felt completely comfortable in their midst. And that comfort obviously was reciprocated. “I understand these folks,” Obama told me on a downstate campaign trip during his U.S. Senate race. “My grandmother was Republican. I grew up with these people.”