Obama - A Promise of Change Part 3

a"JERRY KELLMAN, CHICAGO COMMUNITY ORGANIZER.

Barack Obamaas 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 beforea"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 compet.i.tive politician like Obama, the electoral loss to Rush stung sharply. Obama had entered the contest knowing it would be difficult to unseat an inc.u.mbent. But with his optimistic streak, he believed that if everyday voters could just hear his message, experience his intellect and feel the pa.s.sion 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. Itas about shrewd calculation, raising money, catering to the necessary special interests. Itas about a.s.sembling 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 couldnat vote for him. The reason was summed up by one elderly woman who explained to Obama succinctly: aBobby just ainat done nothina wrong.a 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. aIt 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,a he said. aIt really had more to do with me feeling anxious to be in the mix.a 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 cityas liberal establishment like Abner Mikva. In Springfield, he had ama.s.sed 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 interestsa"the influential political reporters, the legislative powers-that-be, the union leaders, the political insiders. aBarack, you didnat have enough of the people in the party with youa"you were kind of out there on your own,a 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 didnat feel connected to him as an individual. It might be hard to imagine as the years have unfolded and Obamaas 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 rsum, 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 const.i.tutional 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, anch.o.r.ed by the college neighborhood of Hyde Park, but in the broader South Side black community, it could be alienating. Working-cla.s.s voters gathering in neighborhood church bas.e.m.e.nts 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. aIn his race with Bobby Rush, it really taught Barack how to connect to a black audience,a Mikva recalled.

In this respect, Obamaas story is similar to that of one of the countryas most talented and charismatic politicians, a man to whom he is often compareda"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 familyas 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 pract.i.tioners 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 Obamaas own words, he had been aspanked.a 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 soa"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 a.s.sembly. And rather than holding grudges against those who had been less than supportive of him through the congressional contesta"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 legislaturea"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 organizationsa"the prestigious Joyce Foundation perhaps the most important of thesea"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, Mich.e.l.le 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 Mich.e.l.le were living a middle-to upper-middle-cla.s.s, white-collar existence, going home to a s.p.a.cious 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. aI was broke,a Obama recalled. aAnd 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 wasnat accepted. It wasnat a high point in my life.a He could not get a floor pa.s.s 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. aHe is motivated by people and getting things done. He does not think about money,a Sh.o.m.on said. aHe used to forget to put in his expense reimburs.e.m.e.nts for his state trips. I would say, aWhat the f.u.c.k is wrong with him?a 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.a Obamaas 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. aIam sure Mich.e.l.le would have been happier if I would have emphasized that a little more,a his grandmother told me with a small smile. Obamaas 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 wardrobea"perhaps twice weekly. He loathed buying new clothing, telling Mich.e.l.le to pick out a couple of new s.h.i.+rts 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 s.h.i.+rts or mock turtlenecks paired with khaki pants. In casual settings, he gave the appearance of a walking Gap advertis.e.m.e.nt, except that his lagging fas.h.i.+on sense generally would have made the ad a few years old. Mich.e.l.le, 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 jewelrya"just a gold wedding band and his one modest wrist.w.a.tch 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 a.s.sembly, as well as teaching. aThere were a range of options that I examined,a Obama said. aBut, 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 wasnat a time of depression.a The most important relations.h.i.+p Obama improved upon when he returned to the senate was with the senateas Democratic leader since 1993a"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 gra.s.sroots political operation on the cityas 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 Jonesas 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 inst.i.tutions; Jones, twenty-five years Obamaas elder, was one of eight children of a truck driver and a homemaker on Chicagoas South Side who found employment with the cityas 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 Chicagoas machine politics. But as Obamaas 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 p.r.o.nounce Jonesas first name with a midwestern flatness (E-mul), Obama is always careful to p.r.o.nounce it correctly (E-meel). aEmil 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 thata"and I respect that mission,a Obama said. Jones puts his fondness for Obama in more personal terms. aI am blessed to be his G.o.dfather and he feels like a son to me,a Jones said.

As 2002 approached, the political dynamics of Illinois began to alter dramatically. It appeared as if the Democrats could retake the Illinois senatea"and by the November election, that scenario became a reality. Jones became senate president, and Obamaas 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, OBAMAaS AMBITION BEGAN NAGGING AT HIM again. Suddenly he was in a position to pa.s.s 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 inc.u.mbent, 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 Was.h.i.+ngton 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 aput out feelersa to colleagues in the Illinois senate, asking if they would support him in a run for the U.S. Senate, and he agot a pretty favorable response.a Yet nearly everyone close to Obama was unified in their counsel: Donat run.

In addition to his wife, Mich.e.l.le, chief among people dispensing this advice was his top aide and good friend, Sh.o.m.on. 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 wouldnat win, but Sh.o.m.on 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 coupleas 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. Sh.o.m.on said he felt that another hectic campaign would overwhelm Obamaas family life.

Little did Sh.o.m.on 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 positiona"a nine-to-five office job that lacked excitement and adventure.

aHe always talked about the New Roch.e.l.le train, the trains that took commuters to and from New York City, and he didnat want to be on one of those trains every day,a said Jerry Kellman, the community organizer who enticed Obama to Chicago from his Manhattan office job. aThe image of a life, not a dynamic life, of going through the motionsathat was scary to him.a Sh.o.m.on, 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 joba"as head of the Chicago-based Joyce Foundation. aI am thinking that my relations.h.i.+p with a politician is going to pay off! I am going to get this hundred-and-fifty-thousand-dollar-a-year policy job!a Sh.o.m.on said with a laugh. aSo he calls meaand he tells me that he was literally shaking when he went in to the interview for fear that he would get the joba"because he did not want it. I said, aWhat the f.u.c.k is wrong with you?! This is a dream. You can build up money, build up relations.h.i.+ps and run again.a aWe were on the side of the road on Illinois 4 and I told Barack, aI donat think you should run,aa Sh.o.m.on recalled. aI said I thought it was a bad idea because of Mich.e.l.le and the kids. Barack feels tremendous guilt. He has a conscience. I thought he would wish he hadnat done it afterward. But he just looked at me and said, aIam running anyway.aa Winning a U.S. Senate seat was perhaps Obamaas 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 Roch.e.l.le train home from work every day.

CHAPTER.

11.

The Candidate.

The older I get, the more I realize it is not always what you say, but the way you say it. And that is particularly true in politics.

a"HOTEL MAGNATE PENNY PRITZKER.

Barack Obamaas first thoughts about running for the U.S. Senate came as early as mid-2001, less than a year after his stinging defeat by Bobby Rush. After that race, Obama had been approached about running for Illinois attorney general, but discarded the notion for the same reasons Dan Sh.o.m.on warned him away from the Senate run. Said Obama, aI put Mich.e.l.le and the family through such heck with the congressional race and it put such significant strains on our marriage that I could not just turn around and start running all over again, so I pa.s.sed that by.a Coincidentally, the thought of Obama running for the Senate had also occurred to Eric Adelstein, a Chicago-based media consultant for Democrats. Adelstein had scheduled a meeting with Obama for September 2001 to discuss their mutual idea. But little could either man have known what would transpire on September 11 of that year. aSo 9/11 happens and immediately you have all these reports about the guy who did this thing is Osama Bin Laden,a Obama said. aSuddenly Adelsteinas interest in the meeting had diminished! We talked about it and he said that the name thing was really going to be a problem for me now. In fairness to Eric, I think at that point the notion that somebody named Barack Obama could win anythinga"it just seemed pretty dim.a So Obama went back to concentrating on his two jobs as const.i.tutional law instructor and state lawmaker. But by mid-2002, he again was growing restless in his political career. He began toying again with the idea of the Senate contest and he opened serious conversations with his Illinois senate colleagues about the notion. Several seemed receptivea"Denny Jacobs, Terry Link, Larry Walsh and members of the black caucus, including senate president Emil Jones Jr. They promised to support him, even to lead an exploratory committee.

But there was one person whose affirmation was vitala"Mich.e.l.le. Convincing Mich.e.l.le to support him through another campaign was the most significant hurdle Obama had to clear. Mich.e.l.le knew that her husbandas political career was of immense importance to him, but upon hearing his Senate idea, she began to wonder if this optimistic dreamer was going off the deep edge. The couple had two kids, a mortgage and credit card debt. After Obamaas crus.h.i.+ng loss to Bobby Rush, she worried that her husband was about to undertake another lost cause, although, realistically, she worried primarily about finances. Another political race could keep the family in debt, or perhaps plunge it deeper into debt. And even if he won the Senate seat, she thought, their financial condition was not likely to improve.

aThe big issue around the Senate for me was, how on earth can we afford it?a Mich.e.l.le told me. aI donat like to talk about it, because people forget that his credit card was maxed out. How are we going to get by? Okay, now weare going to have two households to fund, one here and one in Was.h.i.+ngton. We have law school debt, tuition to pay for the children. And weare trying to save for college for the girlsa. My thing is, is this just another gamble? Itas just killing us. My thing was, this is ridiculous, even if you do win, how are you going to afford this wonderful next step in your life? And he said, aWell, then, Iam going to write a book, a good book.a And Iam thinking, aSnake eyes there, buddy. Just write a book, yeah, thatas right. Yep, yep, yep. And youall climb the beanstalk and come back down with the golden egg, Jack.aa But Obama was confident that he was destined for more than just a day job running a foundation or practicing law or languis.h.i.+ng in the minority party in the Illinois senate. And for that golden destiny to come to fruition, he knew he had to do his most convincing sales job yet.

Explained Obama, aWhat I told Mich.e.l.le is that politics has been a huge strain on you, but I really think there is a strong possibility that I can win this race. Obviously I have devoted a lot of my life to public service and I think that I can make a huge difference here if I won the U.S. Senate race. I said to her that if you are willing to go with me on this ride and if it doesnat work out, then I will step out of politicsa. I think that Mich.e.l.le felt as if I was sincere. I think she had come to realize that I would leave politics if she asked me to.a Added Mich.e.l.le, aUltimately I capitulated and said, aWhatever. Weall figure it out. Weare not hurting. Go ahead.aa Then she laughed and told him hopefully, aAnd maybe youall lose.a Obama went back to Sh.o.m.on and told him he was in. aSo I told Dan that I had this conversation with Mich.e.l.le and she had given me the green light and that what I want to do is roll the dice and put everything we have into this thing.a Still tapped out from his congressional race, Obama knew he needed start-up cash. So he held a small fund-raiser that netted thirty-three thousand dollars. That allowed him to begin paying Sh.o.m.on as a full-time campaign manager, as well as hiring an office administrator and a full-time fund-raiser.

BEFORE THAT FUND-RAISER, HOWEVER, OBAMA HAD BEEN MAKING other vital moves. He had a crucial meeting with another important crowda"the key financial supporters of his unsuccessful congressional race in 2000. Obama knew that his fund-raising for a Senate campaign had to far exceed what he had raised in his race against Bobby Rush. So he invited a group of African-American professionals to the house of Marty Nesbitt, who had served as finance chairman of his congressional campaign. Nesbitt is the president of a Chicago parking management company and vice president of the Pritzker Realty Group, part of the Pritzker family empire. A tall, slender African American, he had been friends with Obama for years. Their wives were also close, and Nesbittas wife, Anita Blanchard, an obstetrician, delivered both of Obamaas children. The two men played basketball together and mixed with the same Hyde Park neighborhood crowd of young, successful black professionals. Nesbitt was soft-spoken, polite and amiable. He was also extremely active in civic affairs, serving on the boards of Chicagoas Museum of Contemporary Art, Big Brothers/Big Sisters and the United Negro College Fund, among many others.

Not long after Obamaas loss to Rush, Nesbitt had suggested that Obama might want to run statewide in his next contest. It seemed pointless to try to unseat Rush again after failing so miserably. So when Obama addressed the group of black professionals and mentioned his plans for a statewide race, Nesbitt quite naturally a.s.sumed Obama was considering a state office, such as attorney general or treasurer. Then Obama dropped the bomb.

aBarack says he wants to run for the U.S. Senate,a Nesbitt recalled. aBlahhh!! I mean, I literally fell off the couch. And we all started laughinga"and he said, aNo, really, I am gonna run for the U.S. Senate.aa Then Obama proceeded to make a rational argument that he could win such a race. He said that Senator Fitzgeraldas approval ratings were so low that he was destined to lose to a Democrat in 2004. Obama said he believed he could bring together blacks and liberals into a coalition and come out on top in what was looking to be a crowded primary field. aHe convinced us in the room that day that he could pull it off,a Nesbitt said. aBut he mostly convinced us because we were his friends and we wanted to support him.a Obama, who had learned the significance of money in politics during his Rush contest, also told them the hard fiscal truth that he was going to need not hundreds of thousands but millions of dollars to pull off a victory. He even broke it down into specifics, telling the group that with three million dollars, he had a 40 percent chance of winning; with five million dollars, he had a 50 percent chance; with seven million, 80 percent. And with ten million, Obama proclaimed, aI guarantee you that I will win.a Nesbitt said that Obamaas supreme confidence, clear vision and attention to detail convinced them that it was doable. It certainly wasnat a sure win, but it was doable.

aSo we all said, aWeave gotta make a gra.s.sroots, ground-level push and get this going,aa Nesbitt said. aBut you know, at this point, I was very naive. Barack is not afraid to ask for money. But I didnat have any idea how far we had to take it, to the next level.a The next level meant that Nesbitt and Obama had to reach beyond his previous contributor base. In his congressional race, Obama successfully picked up cash from black business leaders and a smattering of lakefront liberals, but he needed to reach even deeper into those pockets and find more. So Nesbitt arranged a weekend getaway to help Obama reach inside the deepest pockets he knewa"those of the Pritzker family.

THE PRITZKERS RULE A FAMILY EMPIRE THAT EMBODIES HIGH society and extreme wealth in Chicago. One of the richest families in the country, with a fortune estimated at twenty billion dollars, the Pritzkers began their American story in 1902 when Nicholas Pritzker, a Ukrainian immigrant, opened a law firm in Chicagoas downtown Loop commercial district. Over four generations the family ama.s.sed its fortune through Hyatt hotels, financial services and numerous other enterprises. The clan is intensely private, even if they have also been extremely philanthropic. Nesbitt knew that if Obama could sell himself to Penny Pritzker, her support would not only reap huge immediate financial dividends but also be a crucial step in the foundation of a fund-raising network.

So in late summer 2002, Obama, Mich.e.l.le and their two daughters drove to Penny Pritzkeras weekend cottage along the lakefront in Michigan, about forty-five minutes from Chicago, to sell his candidacy.

Like many people at this point, Pritzker was impressed by Obamaas intellectual heft but was unsure whether he could pull off what he had in mind. It would be up to Obama to sell his vision to a veteran businesswoman who was no easy sale. Pritzker, who has mostly supported Democrats but deems herself a acentrist,a recalled the weekend as a aseminal moment.a She and her husband, Bryan Traubert, were in training for the Chicago Marathon, and under a beautiful sunny sky the couple slipped away for a long run along Michiganas winding country roads near the lakesh.o.r.e, all the while discussing whether Obama merited their backing. She described the discussion: We had known Barack and Mich.e.l.le previously, but we hadnat made up our minds about supporting him for the Senate. And we had to make a decision. So we spent some time talking with him about his philosophy of life and his vision for the country. He is a very thoughtful human being in the way he articulates ideas and the way he thinks about the world. And the older I get, the more I realize it is not always what you say, but the way you say it. And that is particularly true in politicsa. So Bryan and I had a long discussion about Barack and his values and the way he carries and expresses himself, his family and the kind of human beings he and Mich.e.l.le area"what kind of people they are, as much as about lofty political ideas. Really, at that point the question was, these other people are running and what obligations do you have to the other people? It became clear to us that if Barack could win, he had the intellect, the opportunity, to be an extraordinary leader, not just because he would be an African-American senator, but a male African-American senator. Here is a guy with an amazing intellectual capacity to learn and an interest in learninga. But how much did he know about medicine, about business, about foreign affairs and the economy? He was dealing with all these things in fragments and we asked ourselves what was his capacity to deal with these things as a whole?aHe was someone who views himself as a healer, not a divisive character, but someone who can bring disparate const.i.tuencies togethera. It became clear to us thatahe is not perfect, but he is bright and thoughtful and confident. He possesses a lot of confidence. That was the seminal moment when we simply decided after that weekend that we would support them.

With Penny Pritzker on board, other influential Chicago-based Democrats and philanthropists soon followed suit: Newton Minnow, a Chicago lawyer who advised Senator Adlai Stevenson and Presidents John F. Kennedy and Lyndon Johnson; James Crown and members of the wealthy Crown family; John Bryan, then the chief executive of the Sara Lee Corporation.

Obama had not yet announced his candidacy, but he realized he needed more political talent behind him. By now, Adelstein had signed on with another potential candidate, Gery Chico, the former president of the Chicago Board of Education. So Obama turned to the other major political consultant he knew, David Axelrod. A couple of years earlier, Axelrod and his wife, Susan, had thrown a quick fund-raiser for Obama at their downtown Chicago high-rise condominium when Obamaas senate district lines were redrawn to include much of downtown, including their home. Obama was largely anonymous outside Hyde Park at that first gathering, which drew all of twenty people. aWe were pulling in people from the pool, urging them, aHey, come meet your new state senator,aa Axelrod said.

After this tepid fund-raiser and Obamaas collapse against Bobby Rush, the political consultant was less than enthused about a potential Senate candidacy for Obama. Axelrod told the hopeful Obama that he thought Obama was a aterrific talenta and aI consider you my friend,a but running for statewide office was aprobably unrealistic.a Axelrod was blunt with Obama: aIf I were you, I would wait until Daley retires and then look at a mayoras race because then the demographics would be working in your favor.a That disappointed Obama, but it did not dissuade hima"he still thought the Senate was a good possibility for him. Even so, he soon encountered an even bigger stumbling block than Axelrodas caution. Carol Moseley Braun, who represented Illinois in the Senate from 1993 to 1999, announced that she might run to reclaim the seat she had lost to Republican Fitzgerald. Moseley Braun had made history as the first African-American woman to serve in the Senate but was defeated by Fitzgerald in 1998 after a tumultuous first term. Allegations arose that her then boyfriend, Kgosie Matthews, who ultimately took over her campaign, s.e.xually hara.s.sed female campaign workers, although Moseley Braun said an investigation found no evidence. The couple was accused of spending campaign money on clothes and jewelry, and they were criticized for taking a month-long trip to Africa right after the election. But her major downfall was meeting with the former dictator of Nigeria, General Sani Abacha, without giving advance warning to the Department of State. Abacha had been accused of a host of human rights violations.

Fitzgerald looked extremely vulnerable, having feuded with the GOP power structures in Was.h.i.+ngton and Illinois. This was the major factor that led Obama to think that unseating him was possible. But if Moseley Braun were in the race, Obama said he would have to defer to her and decline to run. The reality was, he would have no choice: she would gobble up both of his potential bases of supporta"African Americans and liberals. aThere was no way to win,a he said. So Obama asked to meet with her in his senate office in Springfield. aWeaasked her how serious she was, and her basic att.i.tude was that she had not made up her mind but obviously it is [her] prerogative to potentially run,a Obama recalled. aI understood her position. She had been a trailblazer. It was frustrating for me to think that maybe this was one chance to go after something I really cared about and potentially [I] could not do it. But that is the nature of politics.a Moseley Braun presented not only a problem for Obama, but a major headache for the Democratic Party powers in both Illinois and Was.h.i.+ngton. Because she had been a national figure as the first black woman in the Senate, her alleged improprieties in office had been a major embarra.s.sment to the party. And even though Fitzgerald appeared extremely vulnerable, Democrats feared that these past embarra.s.sments would doom her in a general election. Eric Zorn, a liberal columnist for the Chicago Tribune, went so far as to predict that she would be awallopeda by almost any Republican. With a Senate seat seemingly up for grabs, Democrats could ill afford to run a candidate tainted with past scandals.

To keep Moseley Braun out of the race, various Democratic powers close to Obama set out to find her a job elsewhere. aBut the problem was, they could not find her employment,a said an Obama confidante. an.o.body could find her any work.a While the job search persisted, Moseley Braunas indecisiveness about a Senate run began to wear thin on the potential candidates and on Democratic activists looking to support someone in the race. It especially wore thin on Obama, whose political career was hanging in the balance. But that apparently did not matter to Moseley Braun (who declined to be interviewed on the subject). aShe felt that [Obama] was a young whippersnapper, a pretender, a cheat,a David Axelrod said. aI think she took it personally. He was essentially messing in her territory. She made it pretty clear that she was not happy about Barackas entrance.a As Moseley Braun considered her options, Obama decided to travel to Was.h.i.+ngton in September 2002, to spend a weekend at the annual Congressional Black Caucus conference in hopes of garnering support for himself. He figured he would meet some influential black lawmakers and ask for their help and guidance. But the excursion was a major disappointment for the earnest Obama. He returned to Chicago significantly disillusioned about the ways of Was.h.i.+ngton.

A couple of weeks after returning home, he sought the counsel of his pastor and friend, the Reverend Jeremiah Wright. Visibly dejected, Obama slumped onto the sofa in the pastoras second-floor office at Trinity United Church of Christ. He told Wright that the Senate idea was thoroughly frustrating him because Moseley Braun would not make up her mind whether she was in or out. And not only that, but other names had begun to surface for the racea"Illinois comptroller Dan Hynes, whose father was a powerful Chicago ward alderman; Blair Hull, a multimillionaire securities trader; and Gery Chico, formerly a top aide to Chicago mayor Richard Daley and school board president. None was a certain nominee or impinged on his bases, but each had strengths, and each was pulling ahead of him in organizing a campaign operation. Hynes had run statewide before and would have his fatheras political machine behind him. Hull would have tens of millions in personal wealth to lavish on a campaign. Chico was already raising significant money and was far along in a.s.sembling a campaign structure. Another name floating around was Representative Jan Schakowsky, a liberal from the North Sh.o.r.e suburbs who would have cut directly into Obamaas lakefront support.

aMy name should be out there,a Obama told his pastor. aBut Carol Moseley Braun wonat say what sheas going to do, and Iam not gonna run against a black woman. If sheas gonna run, then Iam out. Until she says yes or no, I canat say anything.a But what truly struck Wright from that meeting was Obamaas astonishment over the black caucus event in Was.h.i.+ngton. It opened Wrightas eyes once again to just how innocent and idealistic Obama could be about the world of politics. The conference was nothing like what Obama had envisioned, but it was exactly the way Wright, a former adviser to Chicagoas only black mayor, Harold Was.h.i.+ngton, recalled it.

aHe had gone down there to get support and find out who would support him and found out it was just a meat market,a the pastor said in an interview, breaking into a laugh. aHe had people say, aIf you want to count on me, come on to my room. I donat care if youare married. I am not asking you to leave your wifea"just come on.a All the women hitting on him. He was, like, in shock. Heas there on a serious agenda, talking about running for the United States Senate. Theyare talking about giving [him] some p.u.s.s.y. And I was like, aBarack, camon, man. Come on! Name me one significant thing that has come out of black congressional caucus weekend. Itas homecoming. Itas just a nonstop party, all the booze you want, all the booty you want. Thatas all it is.a And here he is with this altruistic agenda, trying to get some support. He comes back shattered. I thought to myself, aDoes he have a rude awakening coming his way.aa A few months later, Moseley Braun was still dithering as Obama took his annual Christmas season sojourn to his native Hawaii. Deeply dispirited over the prospect of Moseley Braunas candidacy, Obama rested on Sandy Beach, a fifteen-minute drive along the rugged southeast sh.o.r.eline from downtown Honolulu. This was the beach of Obamaas youth, the childhood paradise where he spent mindless high school days body-surfing, drinking beer and seeking to convince college women that he was worthy of their attention. With the tree-covered hills of Oahu again cascading behind him, with the tall waves of the Pacific Ocean again cras.h.i.+ng before him, the forty-one-year-old Illinois state senator contemplated his future. At this moment, Obamaas ambitious nature was eating at him. He was terrified that all his hard work was coming to naught. The frustrating years trying to organize programs that would a.s.sist the impoverished on Chicagoas Far South Side, the decision to forgo a lucrative law career for a meagerly paid civil rights practice, the years foraging in the wilderness of a minority party in the Illinois General a.s.sembly, the days and nights away from his devoted wife and two precious daughters to travel the campaign traila"what had this sacrifice done for him and for the world? That Christmas, Obamaas once bright future seemed as if it was cras.h.i.+ng in the surf. Suddenly his grand idea of winning an open seat on the worldas most powerful lawmaking body looked less like a serious notion than a quixotic dream.

For the first time in his professional life, the supremely confident Obama was deeply frightened. He was terrified that the final story of Barack Obamaas political career would be this: Another talented black man with grandiose dreams somehow flamed out and disappeared from public life. Most frightening of all: This story resembled all too much the tale of his fatheras unfulfilled dreams.

But then Obama peered out at his two young girls splas.h.i.+ng in the ocean with Mich.e.l.le. They looked playful and happy. Obama reconsidered his dreams and thought, well, perhaps he was not meant to be a senator or a mayor. aI didnat grow up thinking that I wanted to be a politician,a Obama recalled. aThis was something that happened as a sideline, as a consequence of or an outgrowth of my community organizing, and if this doesnat work out I am fine with it. Kids keep you grounded, and I had to remind myself that it was not all about me and my personal ambitions, that there is a set of broader issues.a But just as Obama was coming to terms with the notion that his grand political career might never happen, he received a phone call that would again put his personal ambitions front and center. He was still in Hawaii when the news came via cell phone: Moseley Braun had decided against running for the Senate and instead would seek the presidency. Obama knew exactly what he needed to doa"and fast. He clicked the cell phone back open and dialed David Axelrod.

CHAPTER.

12.

The Consultant.

David was in his glory. He was the belle of the ball. Everyone wanted him and he was feeding on all the attention.

a"AN ILLINOIS POLITICAL LOBBYIST ABOUT CONSULTANT DAVID AXELROD.

Perhaps the most significant event in Barack Obamaas campaign for the U.S. Senate occurred more than two full years before Illinois voters went to the polls and many months before Obama even made a final decision to run for the seat. This occurrence was a businesslike yet utterly strange final meeting between the highly regarded political consultant David Axelrod and a complete political neophyte with his eyes on the Senate seat, multimillionaire Blair Hull.

The discussions between Axelrod and Hull ultimately pushed Axelrod into the campaign of Obama, rearranging the dynamics of the race and instantly turning the relatively little-known state senator into a serious contender. Without Axelrod as his marketing specialist, itas unclear if Obama would have won the Democratic Party primary. And if Obama had still managed to pull off victory, thereas absolutely no question that he would never have done it in such an astonis.h.i.+ng fas.h.i.+ona"in a way that propelled him to national stardom even before he hit Was.h.i.+ngton. Obama possessed the innate talent for success, to be sure. But Axelrod was the coach who harnessed that talent and ma.s.saged it into its present form, and then he was the publicity agent who sold Obama to Illinois voters. Obama would lean on Axelrod increasingly throughout the 2003a"2004 campaign seasona"and thereafter. If Obama was on his cell phone, which seemed to be at every spare moment, there was a high probability that he was consulting with aAx,a the apt nickname for this cutthroat political operative. Obama would call Axelrod three or four times a day, at all hours of the day and night, seeking his counsel and his wisdom.

Axelrod is a former reporter for the Chicago Tribune who had slogged through several years of political campaigns as a private consultant before establis.h.i.+ng himself as the preeminent message and media adviser for Democrats seeking office in Illinois. His talent for producing television commercials that highlight the best sale points of a candidate is unsurpa.s.sed. A native of New York City, Axelrod is a tall man who was then approaching fifty. He has a thick salt-and-pepper mustache, thinning hair, a perpetual slouch and dark droopy eyes that make him appear continually sad. He has a keen, somewhat scalding sense of humor. But even when tossing off an acidly funny line, he rarely smiles at his own wit.

Whenever I was a.s.signed to cover a political campaign for the Tribune, I would never fail to schedule a breakfast or two with Axelrod near the downtown Chicago high-rise condominium he shares with his wife, Susan, whom he met playing coed basketball in college. It was a mutually beneficial source-reporter relations.h.i.+p. I would endeavor to pick his brain about the race at hand, while he would use the encounters to convey his candidateas message and try to spin a reporter from the influential Tribune. Without fail, a disheveled Axelrod would arrive for these meetings at least twenty minutes late. He was typically outfitted in a baseball cap and wrinkled sports attire, which he might or might not change in the course of his business day. Over one breakfast, he rubbed his eyes hard with the palms of his hands and confessed that he suffers from sleep apnea, a condition in which someone sleeps but fitfully and unrestfully. This made me think that Axelrodas scarily shrewd political mind is always at work, even during sleep. His sloppy eating habits are a well-worn inside joke among those who know him wella"Obama foremost among these wags. During Obamaas 2004 Senate primary contest, I recall a breakfast in which Axelrod fervently pitched his clientas potential star power for minutes on end. But as he extolled the virtues of Obama, I was more in wonder at the seemingly endless length of time that a gooey string of yellow cheese from his omelet could extend from his mustache to his plate without snapping or being noticed by him.

Axelrod has handled media strategy for major Democrats across the nation, including Chicago mayor Richard M. Daley, Representative Rahm Emanuel of Illinois, Senator Christopher Dodd of Connecticut and a host of others. He initially oversaw media for Senator John Edwardsas 2004 presidential campaign but mysteriously left that role amid squabbling among Edwardsas advisers. Axelrod wonat talk about that campaign in depth, except to say that aFor whatever reason, John Edwards couldnat close the deal. The candidate has to close the deal with voters.a Rising from the streets of Chicagoas bare-knuckles, fratricidal machine politics, Axelrod developed a specialty in urban races. He is especially masterful at helping to elect black candidates in broad geographic areas where some white support is essential, most notably Michael White for Cleveland mayor and Deval Patrick for Ma.s.sachusetts governor. He has a special talent for tapping into the most compelling personal life stories of a candidate and composing a campaign script that enhances those qualities for public consumption. Despite this artistic side, Axelrod also has no fear of negative, go-for-the-jugular campaigning. Of all the operatives that Republican strategist Ed Rollins has gone up against, Rollins placed Axelrod at the top of his list of aGuys I Never Want to See Lobbing Grenades at Me Again.a Axelrod did his first political work at nine years of age, when the precocious youngster handed out leaflets for Robert Kennedyas Senate campaign in New York. aI just wanted to go out and do it and so I went over and volunteereda"I was a weird kid,a Axelrod said with a smirk. His mother was a newspaper reporter before running focus groups for a New York advertising agency. His father, a Russian immigrant, was a psychologist and, perhaps most significant to the sports-maniac Axelrod, an excellent baseball player who was an amateur teammate of the great hitter Hank Greenberg, known for making the National Baseball Hall of Fame after overcoming virulent anti-Semitism. Axelrodas father went to Long Island University on a baseball scholars.h.i.+p and studied art and philosophy before turning to psychology. Axelrodas parents, who would divorce during his childhood, were pa.s.sionate about politics and acla.s.sic New York leftists,a he said. This philosophy remains with Axelrod today. He is a potent blend of irascible left-wing idealist and smooth-talking, high-priced operative for the establishment. He talks with such deep conviction about using politics to promote the greater good that it is impossible to think he does not believe this at some level. On the other hand, one of Axelrodas most enduring clients is Mayor Daley, who lords over Chicago with a powerful political machine unmatched anywhere in the country. When Daleyas political apparatus became the focus of a federal corruption investigation into widespread illegal patronage hiring at city hall, Axelrod rushed to defend the mayor with TV appearances and op-ed pieces. He explains this moral contradiction by saying that Daleyas overall record is one of bringing harmony and development to a city that the mayor clearly loves.

Axelrod has been dealt two family tragedies that perhaps explain why I have always sensed a certain melancholy about him. His father committed suicide while Axelrod was in college, and his only daughter among three children became developmentally disabled after suffering epileptic seizures.

For years, Axelrod was loath to acknowledge his fatheras suicide. Whenever I tried to broach the subject, he would deftly skirt around it, and I would retreat. But in 2006, Axelrod finally came to terms with the loss. He wrote a poignant column in the Tribune about his fatheras chronic depression: aDad never shared his anxieties or sadness with me or, so far as I could tell, anyone else. At his funeral, several of his patients told me that he had saved their lives. Yet he couldnat reach out for help to save his owna. We still have a long way to go before depression and other psychiatric conditions are fully accepted as illnesses, not defects of character or failures of self-discipline. I know, because itas taken me more than thirty years to say out loud that the man I most loved and admired took his own life.a Axelrod came to Chicago to study political science at the University of Chicago and, just days after graduation, found himself following his motheras profession, covering nighttime amayhemaa"cops, courts, killingsa"for the Tribune. He worked his way up to political reporter and was largely responsible for a great deal of good press coverage of the 1979 campaign of an outsider for Chicago mayor, Jane Byrne. In fact, Axelrodas reporting was instrumental in Byrneas upset victory to become the first woman to head city hall. After her election, Axelrod then dutifully chronicled every election promise that she broke, and essentially reversed her image from reformer to another go-along politician. Thus, Axelrod is intimately familiar with how the media often operates, having been a purveyor of its duplicitous nature. The press can carry a candidate into office on one day and knock that politician out of office the next. Set aem up, then knock aem down.

Axelrodas stay with the Tribune ended in 1984 after, in his version, he grew concerned about the newspaperas direction away from a asense of missiona and toward acorporatization.a He talks nostalgically of his reporting days at the Tribune. aIt was just all about the journalism and the mission,a he said. aYou would have loved working then.a Axelrod had a front-row seat for Harold Was.h.i.+ngtonas historic mayoral run and the racial animosity it stoked in the city. But missions aside, Axelrod also departed the Tribune because his career hit a roadblock. He had sharp differences with more senior reporters and editors who stood in his path. Upon leaving the newspaper, Axelrod was immediately hired as communications director for the successful Senate campaign of then Representative Paul Simon, whose devotion and integrity ainspireda Axelrod. After a shakeup in Simonas staff, Axelrod quickly found himself comanaging the campaign of the bespectacled, bow-tied, populist Democrat. Still in his twenties, Axelrod went from newspaper reporting to overseeing a major Senate campaign almost overnight. It was in Simonas campaign that Axelrod formed a lasting friends.h.i.+p with another young Chicago operativea"the brash, youthful, hard-driving Rahm Emanuel, who went on to become a top White House aide to Bill Clinton and then a leading Democrat in Congress. The merciless Emanuel was chief architect for the Democratsa takeover of the House of Representatives in 2005.

When Axelrod left the newspaper for political consulting, he carried with him a Rolodex of media contacts and intimate knowledge of how deeply politics and newspapers are intertwined in Chicagoas culture and how the inside players of that world operated. It would take time, but this knowledge would help him build a lucrative media consulting business that is thriving more than two decades latera"with his top client, of course, now being Obama.

THE MEETINGS BETWEEN AXELROD AND BLAIR HULL, WHICH occurred throughout 2002, provided Axelrod with a vivid glimpse into the private life of Hull, a former professional Las Vegas gambler who had ama.s.sed extraordinary personal wealth trading securities on Wall Street.

Hull was willing to spend tens of millions to win a Senate seata"and he wanted Axelrod on board his campaign. Axelrod was especially accomplished at spotting and a.s.sessing the modest or far-reaching talent possessed by a candidate, as well as at crafting a message and articulating that message through appealing television advertising. But just as important, as a former Tribune reporter, he offered those invaluable inside connections to Chicagoas media elite. He could call nearly any political reporter or newspaper editor in the Chicago region, including those in the often impenetrable Tribune ivory tower, and immediately get an audience. Axelrod had cultivated reporters throughout Chicago and the rest of the state. (Full disclosure: I was among those reporters under cultivation.) From his earlier stint at the Tribune, Axelrod was also on a friendly, first-name basis with the editor of the Tribune, Ann Marie Lipinski, as well as with its editorial board editor, Bruce Dold. He throws an annual December holiday party in which the guests are split almost evenly between media members and political insiders. Thus, each serious candidate in the 2004 Senate contest ranked Axelrod the overwhelming first choice among media advisers to hire. aDavid was in his glory. He was the belle of the ball,a one influential Illinois political lobbyist recalled. aEveryone wanted him and he was feeding on all the attention.a In being the sought-after adviser, Axelrod was dealing from a position of extreme power when selecting an employer. No one grasped the demographic and political dynamics of the entire state and urban Chicago as astutely as Axelrod. He knew the terrain and the people who populated that landscape. The candidate who won his services would have the sharpest, most ruthless political mind in the state at his disposal, immediately providing that person with a huge advantage amid a compet.i.tive field.

For those like Axelrod who ply their trade in the meat-grinder of campaign politics, Hull was the employer of choice. Hull not only brought immediate national attention to the race because of his excessive wealtha"several hundred million dollarsa"but most important to itinerant political workers, he offered an unlimited bank account from which to fund a campaign. Hull had pledged to spend tens of millions of dollarsa"whatever it took to win the seat. And best of all, he was such a newcomer to politics that he was at the mercy of his paid staff about nearly everything, from what to say to reporters to how much to drop on television ads. His campaign manager, for example, struck a one-hundred-and-fifty-thousand-dollar-a-year deala"an over-the-top sum to run a Senate campaign. Hull was a cash cow all too willing to be milked prodigiously. aHe was a meal ticket for everybody,a in the words of Axelrod.

Axelrod also had a history of signing with a deep-pocketed first-time candidate like Hull. In 1992 he was chief adviser to free-spending multimillionaire lawyer Al Hofeld when Hofeld unsuccessfully sought the Democratic nomination against Senator Alan Dixon of Illinois. So when the 2004 Senate race rolled around, Axelrod looked first to Hull. By Axelrodas account, he met with Hull at least twice in the first half of 2002. Hull told Axelrod that he had already hired a highly recommended Was.h.i.+ngton-based media consultant, Anita Dunn. Yet, according to Axelrod, Hull promised him double Dunnas fee if he would come on board too. aI would have made far more money working for Hull in the primary than what I made from Barack in both the primary and the general [elections] combined,a Axelrod said.

Still, none of the meetings between Axelrod and Hull went particularly well for the awkward Hull. And most important, the encounters provided Axelrod with extraordinary insight into Hullas character and his astounding lack of political talent. In their first chat, Hull misinterpreted Axelrodas concern about Hullas dismal history of voting in elections as a veiled threat to be used against him later. In subsequent discussions, Axelrod learned intimate and sordid details about Hullas private life that would later be of significant value to Axelrodas ultimate employer, Barack Obama.

Rumors had swirled in Democratic circles that Hullas divorce had been particularly messy, and that his ex-wife had made allegations against him, although the specifics of those allegations were unclear. Talk that Hull had a past alcohol abuse problem also floated through the political air. Learning of this through the grapevine, Axelrod could see a complicated future for a Hull candidacy. If these things were true, Hull could go up in flames, especially if the public relations surrounding these matters was not handled with expert perfection.

So Axelrod questioned Hull sternly and specifically about the rumors. He wanted to know exactly what kind of storm he might have to weather if he signed with Hull. And he wanted to know how Hull would handle himself should those rumors be proved factual and then leak into the public domain. Realizing the importance of enlisting Axelrod on his team, Hull decided to come clean with hima"sort of. Hull acknowledged that he indeed had used cocaine in the past and had sought treatment for alcohol abuse and that, yes, his ex-wife had alleged physical and mental abuse.

But to Axelrodas astonishment, when he pried further about the ex-wifeas allegations of abuse, Hull gave him an answer that ultimately would end their relations.h.i.+p. Axelrod explained to Hull: aYou know, I hear these things. I donat know if theyare true. But you know, like I need to know if theyare true.a The multimillionaire gave Axelrod a look that Axelrod would later describe as aglacial.a Then Hull simply said: aThereas no paper on that.a Recalled Axelrod: aSo Iam thinking, Wow, thatas really not the answer you really wanted to heara. And I am thinking, Heas a cold guy. I finally came to that conclusion. I also came to the conclusion that he could not get through the primary with that stuffa. I told him that he needed to think real long and hard about this because these kinds of things come out. It was a really awkward thing, though, because I knew stuff from a conversation that I felt was, in certain ways, privileged. I knew all this s.h.i.+t but I could not, and would not, use it against him.a Nevertheless, if Axelrod wanted some business from the 2004 Senate contest, after those talks, it became clear that he must find another Democrat to pay his bills.

LESS THAN TWO MONTHS BEFORE OBAMAaS SEASONAL HAWAII vacation in 2002, he delivered what he considers today to be his best speecha"an address to a group of hundreds of war protestors in which he flatly stated his opposition to a U.S. invasion of Iraq. The American military action was still months away, but foment had been building against it, especially among the Democratic Partyas left wing. Still, just a year after the 9/11 terrorist strike, President Bushas favorable rating among voters was very high. Polls showed that most Americans supported him if he ultimately deemed the invasion to be in the best interests of the countryas foreign policy.

As a still unannounced Senate candidate, Obama for months had been quietly courting what he considered his two strongest bases of supporta"Chicagoas so-called lakefront liberals and African Americans. The lead organizer of the downtown Chicago anti-war rally was Bettylu Saltzman, a liberal stalwart among the cityas elite lakefront crowd whose admiration for Obama dated back more than a decade. Saltzman, a pet.i.te woman in her early seventies at this time, was the daughter of a late Chicago-area builder, Philip Klutznick, who left a fortune to Saltzman and her five brothers. Klutznick had held top posts in the administrations of Franklin Delano Roosevelt, John F. Kennedy and Jimmy Carter. Of Klutznickas children, Saltzman was the one drawn to political activism. She had been aenraptureda by the speeches of Adlai Stevenson, the senator from Illinois who lost the 1962 Democratic presidential nomination to Kennedy. At the Democratic National Convention in Chicago in 1968, she worked on behalf of Eugene McCarthy, the antia"Vietnam War candidate for president. But her biggest political role came when, for four years, she ran the Chicago-based office of Senator Paul Simon. While working for Simon, Saltzman formed a close bond with one of Simonas chief political mindsa"Axelrod, who had comanaged Simonas first Senate campaign. The two would talk on the phone almost daily, each sharing a pa.s.sion for political gossip and Chicago Bulls basketball. By 2002, Saltzman was a major Chicago fund-raiser who could not only tap into her own wealth but had big-money connections that could help raise substantial cash for any political candidate.

Saltzman first met Obama in 1992 after he graduated from Harvard Law and moved back to Chicago to practice civil rights law. Saltzman was volunteering for Bill Clintonas campaign and was a.s.sembling const.i.tuency groups when Obama stopped into Clintonas Chicago campaign office. Saltzman was immediately struck by Obamaas understated presence. aHe came in and not only did he speak well, but it was just the way he presented himself,a Saltzman said. aHe had never run for office, but he had all those qualities of a skilled politician.a Saltzman and Obama formed a lasting political friends.h.i.+p and she was helpful to Obama when he ran for the Illinois senate. When I interviewed Saltzman about Obama, it was readily evident that his appeal to her went beyond the normal politicianas. Having mentioned that she was aenraptureda by Adlai Stevenson, Saltzman said she felt the same way about Obama, only more so. She seemed almost spellbound by him, in fact. aWhen he speaks, itas likea"itas like magic.a So when Saltzman was a.s.sembling speakers for the anti-war rally in late October 2002, Obama came to her mind. Saltzman knew from conversations with the lawmaker that he did not support an Iraq invasion, and she called him and asked him to partic.i.p.ate in the rally. Obama, still an unannounced candidate for the Senate, did not immediately agree, but he told Saltzman that he would think it over. This was one of the biggest decisions of his potential Senate bid. Should he take a public