He always talked about the New Rochelle train, the trains that took commuters to and from New York City, and he didn’t want to be on one of those trains every day. The image of a life, not a dynamic life, of going through the motions . . . that was scary to him.
—JERRY KELLMAN, CHICAGO COMMUNITY ORGANIZER
Barack Obama’s ill-fated race against Bobby Rush taught the young state lawmaker a host of crucial lessons, not the least being that, in politics, no matter how appealing you are as a candidate and no matter how impressive your credentials, you are never completely in control of your own destiny. Something as random as a drug-related shooting can alter an election in such a profound way that not even the most sagacious political forecaster could predict it.
Obama had learned a similarly hard lesson about the vagaries of life once before—when despite his hard work and intense desire, he was benched from the basketball team at Punahou Academy after arguing with the coach about playing time. Yet for an incredibly competitive politician like Obama, the electoral loss to Rush stung sharply. Obama had entered the contest knowing it would be difficult to unseat an incumbent. But with his optimistic streak, he believed that if everyday voters could just hear his message, experience his intellect and feel the passion in his heart, he could win them over. But politics is about more than just delivering an appealing message or being on the right side of the issues. It’s about shrewd calculation, raising money, catering to the necessary special interests. It’s about assembling a coherent strategy to win and then executing that plan.
When Obama stood outside a polling place and shook hands with voters on election day, he realized that he had gravely miscalculated. One after another, voters told him that they liked him, that they thought he offered a lot to public life and had a bright future, but they couldn’t vote for him. The reason was summed up by one elderly woman who explained to Obama succinctly: “Bobby just ain’t done nothin’ wrong.” Obama said it became clear to him that he had put himself ahead of the electorate, that his own time frame for advancement was not necessarily the same time frame that voters saw for him. “It made me realize that, you know, they were right, that there was no great external imperative for me to be a congressman at that stage,” he said. “It really had more to do with me feeling anxious to be in the mix.”
Obama learned that success in politics, as in life, requires balancing fierce ambition with due patience. On the campaign trail, as in the television debate, Obama looked too much like a man in a hurry. By then, he had published a book, led the most prestigious law journal in the country, been profiled in national publications and been embraced by various elites in Chicago, from the Tribune editorial board to guardians of the city’s liberal establishment like Abner Mikva. In Springfield, he had amassed some success as a first-term lawmaker, but he was perceived by some as ineffectual because he had not curried enough favor with the right interests—the influential political reporters, the legislative powers-that-be, the union leaders, the political insiders. “Barack, you didn’t have enough of the people in the party with you—you were kind of out there on your own,” his friend and counselor the Reverend Jeremiah Wright told him.
But even if the right people were behind him, that could be of little worth if the voters didn’t feel connected to him as an individual. It might be hard to imagine as the years have unfolded and Obama’s skills as a politician have been seen worldwide, but he was an extremely poor political candidate in that race. By most accounts, in the Rush contest Obama was too fond of reciting his impressive résumé, too often mentioned that he had forsaken a high-priced law firm for public office and too often spoke in the high-minded prose of a constitutional law lecturer, all of which could make him appear condescending to his audience. That tone might have played well with a majority of voters in his state senate district, anchored by the college neighborhood of Hyde Park, but in the broader South Side black community, it could be alienating. Working-class voters gathering in neighborhood church basements want to know specifically how a candidate is going to work to change their lives. These black voters, in particular, want to feel that a candidate is committed to their cause and not to furthering his own career. “In his race with Bobby Rush, it really taught Barack how to connect to a black audience,” Mikva recalled.
In this respect, Obama’s story is similar to that of one of the country’s most talented and charismatic politicians, a man to whom he is often compared—John F. Kennedy. As with Obama, it might be hard to believe that JFK was initially a poor stump campaigner. But at the outset of his political career, instead of working a room with handshakes and grins, the introverted Kennedy would disappear into a small group and rarely come up for air. Given his family’s wealth and his elite education, Kennedy, too, was initially viewed by some as a condescending elitist. But slowly, as his campaign for Congress unfolded, Kennedy learned the value of pleasing oratory and press-the-flesh connections with everyday voters, until he grew into one of the most skilled practitioners of this aspect of politics. If Obama were to experience success down the road, he needed to absorb the same kinds of lessons about politics from his Rush experience.
When Obama returned to Springfield, his colleagues and friends noticed a changed man, a more chastened figure. He was no longer the bright young guy from Harvard Law School beloved by the liberals and primed for a big political office; he was the brash guy who aimed a little too high, too fast, and had come up way short. He had not just lost to Rush, but in Obama’s own words, he had been “spanked.” His poker crew was comforting but not surprised by the pounding Obama had taken at the polls. State senator Terry Link and others had warned him that dislodging a sitting congressman like Rush would be close to impossible. When Obama sat down with these buddies, he started off by saying he knew that they had told him so—and it need not be said again.
Yet instead of sulking, Obama impressed his colleagues and friends by putting his head down and diving back into the trenches of the General Assembly. And rather than holding grudges against those who had been less than supportive of him through the congressional contest—such as Donne Trotter, the state senator who accused him of lacking black authenticity; and Rich Miller, the Springfield scribe who had criticized his performance in the legislature—Obama sought them out and worked to improve relations. (The one burned bridge that could not be repaired, at least not for years, was with Rush, who now harbored a deep grudge against Obama.)
Obama conducted some soul searching upon returning to Springfield and to his college lecturing. He wondered if politics truly was the avenue he wanted to keep traveling. In 2001 his second child, Sasha, was born, making his commitment to family that much stronger. He had been appointed to the boards of several nonprofit organizations—the prestigious Joyce Foundation perhaps the most important of these—and maybe it was time to think about seeking a full-time post as the director of one of these groups. After all, he was still in the minority party in the senate and there were no guarantees that Democrats would regain power anytime soon. How effective could he be? Moreover, with a second child to tend to, Michelle longed to have a husband with a more stable working life. And financially, the congressional campaign had not been kind. His campaign had spent nearly five hundred and fifty thousand dollars on the race, with thousands coming out of pocket from Obama.
He and Michelle were living a middle- to upper-middle-class, white-collar existence, going home to a spacious town house in Hyde Park and employing a caregiver to help with child care. But despite their combined incomes, which topped $250,000 a year, Obama had personal debt. He had maxed out his credit card, partly on campaign expenses, and the couple were both repaying student loans from Harvard. He had no immediate future in terms of higher office and no law clients because he had suspended his legal practice to challenge Rush full-time. When a friend encouraged him to attend the Democratic National Convention in Los Angeles in the summer of 2000, he said he lacked the resources to go. Ultimately, he found an inexpensive Southwest Airlines flight and made the trek. But upon arrival at the Los Angeles airport, the rental car agency rejected his credit card. “I was broke,” Obama recalled. “And not only that, but my wife was mad at me because we had a baby and I had made this run for Congress. I tried to rent a car in Los Angeles and my credit card wasn’t accepted. It wasn’t a high point in my life.” He could not get a floor pass to the convention, made few networking connections and, in a state of dejection, he wound up returning home by midweek.
This was perhaps the first time that Obama began to consider the importance of money to his personal life. He had always been generous to his employees and friends when it came to money, making it a point to provide holiday bonuses to his staff. But personally, he had never been money-motivated, and he had never sought expensive possessions. In fact, quite the opposite. “He is motivated by people and getting things done. He does not think about money,” Shomon said. “He used to forget to put in his expense reimbursements for his state trips. I would say, ‘What the fuck is wrong with him?’ His wife would thank me for being their accountant! But he was never cheap. A staff member was getting married and Barack wrote her a generous check. He is not a cheap guy at all. If I went to Barack and asked to borrow five thousand dollars, he would do it. He is really generous.”
Obama’s lack of emphasis on money extends to his personal tastes and his other minimalist tendencies. As he was growing up in Hawaii, it was only his grandmother who placed any real emphasis on money, and she was very pragmatic about it. “I’m sure Michelle would have been happier if I would have emphasized that a little more,” his grandmother told me with a small smile. Obama’s minimalistic nature can be seen in his physical appearance during that period. After entering politics, he always looked sharp in a crisp blue or black suit, and he certainly had a smart sense of how to look presentable. But he had only four or five suits in his closet. When spring rolled around, his one khaki suit would be added to his weekly wardrobe—perhaps twice weekly. He loathed buying new clothing, telling Michelle to pick out a couple of new shirts and ties for him at Christmas. His socks were worn in the heels, and his charcoal wool winter coat was a decade old with frayed lining. With his ultra-thin physique, most clothing looked good on Obama, and he was particularly fond of plain black polo shirts or mock turtlenecks paired with khaki pants. In casual settings, he gave the appearance of a walking Gap advertisement, except that his lagging fashion sense generally would have made the ad a few years old. Michelle, later to be joined by his children, would push Obama to wear more colorful garb, or at least patterns and stripes. But he was satisfied with plain whites, blacks and khakis. True to his nature, Obama refrains from cologne and wears little jewelry—just a gold wedding band and his one modest wristwatch with dark leather strap.
Being somewhat financially bereft after the Rush contest, Obama began thinking about seeking a tenured position at the University of Chicago or with a nonprofit group. But he could not see himself making the transition to a more traditional career. Instead, he put off such a move and tried to satisfy himself by knuckling down and working hard in the General Assembly, as well as teaching. “There were a range of options that I examined,” Obama said. “But, you know, I continued to enjoy just the day-to-day work of drafting bills and, you know, framing debates. And so it was a time of reflection, but it wasn’t a time of depression.”
The most important relationship Obama improved upon when he returned to the senate was with the senate’s Democratic leader since 1993—Emil Jones Jr., a street-tough African American who had risen from Chicago sewer inspector to enter the corridors of power in Springfield. Jones is one of the least eloquent speakers among politicians of his success. He has a thick voice that sometimes comes across as a deep mumble, making him difficult to understand. But Jones has been one of the most influential black politicians in the state over the past two decades, building a grassroots political operation on the city’s South Side that could not be challenged. His power among Democrats in the legislature is undisputed and also rarely challenged. If Obama wanted to get his name on key pieces of legislation, Jones was the man to convince. Obama had actually met Jones while he was still a community organizer. He had organized a neighborhood meeting near Jones’s home, and when the meeting expanded into a small march, Jones stepped outside to see what was going on. The two men could not have come from more different backgrounds: Obama was raised in a white family in Hawaii and educated in elite institutions; Jones, twenty-five years Obama’s elder, was one of eight children of a truck driver and a homemaker on Chicago’s South Side who found employment with the city’s sanitation department, presumably with the help of his father, who was also a formidable precinct captain for the Democratic Party. Jones grew up in the belly of Chicago’s machine politics. But as Obama’s career evolved in Springfield, Obama and Jones would grow so close that Jones would talk about the fatherless Obama as a blood son. Obama consistently paid Jones the utmost respect. While most people pronounce Jones’s first name with a midwestern flatness (E-mul), Obama is always careful to pronounce it correctly (E-meel). “Emil is driven by a sense that the African-American community has not been given its fair share and he is trying to make up for that—and I respect that mission,” Obama said. Jones puts his fondness for Obama in more personal terms. “I am blessed to be his godfather and he feels like a son to me,” Jones said.
As 2002 approached, the political dynamics of Illinois began to alter dramatically. It appeared as if the Democrats could retake the Illinois senate—and by the November election, that scenario became a reality. Jones became senate president, and Obama’s career as a legislator took a decisively sharp turn, veering out of the wilderness of the minority party and into the bright lights of the majority.
THROUGHOUT 2002, OBAMA’S AMBITION BEGAN NAGGING AT HIM again. Suddenly he was in a position to pass laws, but he still had his sights set on higher office. The question: Which office to seek? It was about this time that Obama began to think about the U.S. Senate race in 2004. It looked as if the Democratic nominee would face an incumbent, Republican Peter Fitzgerald. Unseating a sitting senator would typically be considered a difficult task. But Fitzgerald had been such an outspoken, go-it-alone maverick in his first term that he had alienated established members of his own party, both in Washington and Illinois. For that reason and others, he looked particularly vulnerable, giving Obama and many other Democrats hopes of reclaiming the seat that, before Fitzgerald, had been held by the first African-American female senator, Democrat Carol Moseley Braun.
Obama said he “put out feelers” to colleagues in the Illinois senate, asking if they would support him in a run for the U.S. Senate, and he “got a pretty favorable response.” Yet nearly everyone close to Obama was unified in their counsel: Don’t run.
In addition to his wife, Michelle, chief among people dispensing this advice was his top aide and good friend, Shomon. He offered this viewpoint to Obama as a friend, not as a paid consultant. Sure, Obama would be a long shot in the Senate race and probably wouldn’t win, but Shomon believed that Obama would regret getting into the race not because of another political failure, but because it would strain relations with his family. In 2002 the couple’s second child, Sasha, was just a year old and the eldest, Malia, was only four. Obama had been regularly absent from the household for months in 1999 and 2000 in his campaign against Bobby Rush, something that still did not sit well with his wife. Now, with two children, Obama just two years later was considering an ambitious statewide contest that would consume even more time than a district congressional race. Shomon said he felt that another hectic campaign would overwhelm Obama’s family life.
Little did Shomon know at the time, but Obama had been seriously exploring the Senate race through the year and had all but made up his mind. To Obama, this was his best, and likely his last, shot at advancing his career in politics. It was clear by now that Bobby Rush would hold his congressional seat for as long as he wanted. So where else was Obama to go? Perhaps he could run for a state office, but other Democrats were in line ahead of him for those positions. Obama had interviewed for private sector jobs, as head of nonprofit foundations. But his restless soul and driving ambition had given him an intense fear of winding up in such a prosaic societal position—a nine-to-five office job that lacked excitement and adventure.
“He always talked about the New Rochelle train, the trains that took commuters to and from New York City, and he didn’t want to be on one of those trains every day,” said Jerry Kellman, the community organizer who enticed Obama to Chicago from his Manhattan office job. “The image of a life, not a dynamic life, of going through the motions . . . that was scary to him.”
Shomon, on the other hand, was ecstatic at the prospect of Obama landing a position as the executive of a nonprofit agency. Obama, in fact, interviewed for such a job—as head of the Chicago-based Joyce Foundation. “I am thinking that my relationship with a politician is going to pay off! I am going to get this hundred-and-fifty-thousand-dollar-a-year policy job!” Shomon said with a laugh. “So he calls me . . . and he tells me that he was literally shaking when he went in to the interview for fear that he would get the job—because he did not want it. I said, ‘What the fuck is wrong with you?! This is a dream. You can build up money, build up relationships and run again.’
“We were on the side of the road on Illinois 4 and I told Barack, ‘I don’t think you should run,’” Shomon recalled. “I said I thought it was a bad idea because of Michelle and the kids. Barack feels tremendous guilt. He has a conscience. I thought he would wish he hadn’t done it afterward. But he just looked at me and said, ‘I’m running anyway.’”
Winning a U.S. Senate seat was perhaps Obama’s last chance at leading that dynamic life that he had told Jerry Kellman he craved. It was his last chance not to take the New Rochelle train home from work every day.