Young Mr. Obama (10 page)

Obama and Ayers both served on the board of the Woods Fund, a foundation that had supported Obama's work as a community organizer. But their biggest project together was the Chicago Annenberg Challenge. In 1993, Walter Annenberg, the Daddy Warbucks publisher of
TV Guide
and former ambassador to the United Kingdom, announced that he planned to spend $500 million to reform urban schools across America. Ayers co-wrote a grant proposal for Chicago, remarking on the overlap between the Challenge and school reform efforts that had begun with the local school council law.

“Chicago is five years into the most far-reaching attempt to restructure a major urban school system ever attempted,” Ayers wrote in the proposal. “The Chicago reform law unleashed enormous amounts of civic energy around education. Since 1989, a strong and growing infrastructure of resources, created by community groups, civic associations, the business community, universities, social service agencies, and neighborhood organizations working with one or a cluster of schools, has been developed to support schools. Foundation and corporate grants to groups working on public education have quadrupled.”

Annenberg gave Chicago $49.2 million, with the understanding that the local chapter would raise double that amount over the next five years. Obama was nominated for the Chicago Annenberg Challenge's board by Deborah Leff, president of the Joyce Foundation, which had funded the Developing Communities Project and had named Obama to its own board the year before. (The Joyce Foundation became a major contributor to the Annenberg Challenge.) As a thirty-three-year-old associate of a small law firm, Obama was the least-distinguished member of the group, which included the vice president and general counsel of Ameritech and the president of the University of Illinois. But at the first meeting, at the Spencer Foundation, an educational research fund with offices in a posh Michigan Avenue office tower, Obama was elected president.

From his new position inside the establishment, Obama reached back to help the neighborhoods where he'd worked as a community organizer. This was why he'd gone to Harvard. Instead of begging his state senator for five hundred grand to help a few South Side high schools, Obama now controlled millions, which could be spread out over an entire school district. The Challenge gave $100,000 to a DCP-sponsored group that aimed to increase family involvement in Roseland schools. It wasn't much different from the tutoring project he'd started with Johnnie Owens.

In its five years of existence, the Annenberg Challenge handed out 210 grants, almost all to elementary schools. The idea was to fund projects that gave teachers time for professional development, reduced class sizes, and connected schools. Schools were grouped into “networks,” so several could participate in each program. The New Schools Multicultural Network, in a Latino neighborhood on the Southwest Side, got $650,000 to encourage English proficiency among parents and Spanish proficiency among students. The South Side African Village Collaborative received $27,500 to place six “village elders” in each of ten South Side schools. (Among them Bryn Mawr Elementary, Michelle Obama's alma mater.) The Challenge also funneled $264,000 to the Small Schools Workshop, which was chaired by Ayers. That money came directly from the Joyce Foundation, which meant Obama was involved in approving it twice.

A few schools claimed big successes. Galileo Scholastic Academy hired a full-time literacy coordinator who put teachers through Great Books training and started a young authors contest. In five years, Galileo nearly doubled the percentage of students reading above the national norm.

Chicago is an enormous school district—at the time, it had 410,000 students—so even $150 million was spread thinly. Each Challenge school got an average of $47,000—just 1.2 percent of a typical annual budget. After the Challenge ended, a study by the University of Illinois at Chicago found that the money hadn't made much difference.

“Our research indicates that student outcomes in Annenberg schools were much like those in non-Annenberg schools and across the Chicago school system as a whole, indicating that among the schools it supported, the Challenge had little impact on student outcomes,” the study concluded.

Student academic engagement was “slightly greater” in the Annenberg schools. Classroom behaviors, sense of self-efficacy, and social competence were all “weaker.”

Do-gooder money distributed from a downtown office building could not alter the demographics of the Chicago Public Schools: 85 percent of the students were black or Latino. An equal number came from low-income families. When Walter Annenberg conceived the Challenge, he wondered why the whole world wanted to attend America's colleges but not its public schools. His half billion dollars didn't change that. Obama's first daughter, Malia, was born while he headed the Challenge. Like most well-to-do Hyde Parkers, he ended up sending her to the Lab School.

The Annenberg Challenge undoubtedly helped Obama. It put him at the head of a major civic undertaking and placed him alongside the city's wealthiest philanthropists. The board met monthly for the first six months and quarterly after that. Obama's duties included meetings with Vartan Gregorian, president of Brown University. When Obama and Gregorian lunched at the Metropolitan Club, they were joined by Maggie Daley, the mayor's wife; Scott Smith, publisher of the
Chicago Tribune
; and Penny Pritzker, a member of the family that has used its multibillion-dollar Hyatt Hotels fortune to stick its name on theaters, libraries, parks, and the University of Chicago's medical school. Five years after that luncheon, Pritzker would become the first big-money donor to support Obama's U.S. Senate campaign. As a candidate for the state senate, he listed the Annenberg Challenge on his campaign literature alongside his civil rights work.

Bill Ayers wasn't Obama's “terrorist pal,” as right-wingers would one day claim. But he was more than just a “guy who lives in my neighborhood,” Obama's attempt to brush off the relationship. They were colleagues, members of overlapping social and professional circles, but they weren't close friends.

Obama
was
friends with Rashid Khalidi, the controversial Arab-American scholar. He had much more in common with Khalidi than with Ayers. Both were outsiders to Chicago, both had Muslim fathers, both had distinguished themselves at influential universities. Khalidi was born in New York City, the son of a Lebanese Christian mother and a Palestinian father who worked at the United Nations. An Oxford Ph.D., he headed the U of C's Center for International Studies. Author of
Palestinian Identity
, Khalidi supported a Palestinian state and harshly condemned America's unwavering support for Israel. The campus newspaper, the
Chicago Maroon
, called him “a University personality both revered and reviled for his heavy criticism of the State of Israel and American policy.” Obama and Khalidi shared the sort of friendship that world-class universities foster. Even though Obama had settled in Chicago and married into a Chicago family, he was still the son of Honolulu, Jakarta, and New York. His outlook was as much global as it was local. He would be far more engaged by a discussion of Middle Eastern policy in the dining room of International House than an argument about the White Sox's pitching staff at Jimmy's Woodlawn Tap. Like Obama, Khalidi would go back east to realize his ambitions. In 2003, he was named the Edward Said Professor of Middle Eastern Studies at Columbia University. During a farewell party, Obama toasted him warmly, recalling conversations that had given him “consistent reminders of my own blind spots and my own biases.”

Dreams from My Father
was finally published in 1995. Obama gave a reading for two dozen friends in the back room of 57th Street Books and managed to cause a small stir in Hyde Park.
Dreams
was reviewed in the
New York Times
(“persuasively describes the phenomenon of belonging to two different worlds, and thus belonging to neither”) and the
Washington Post
. Just as impressively, it scored Obama a feature story in the
Hyde Park Herald
, the neighborhood weekly. A lot of Hyde Parkers write books. It's the local industry. To really impress someone with your intellectual achievements, you have to win a Nobel Prize, and even those are a bit commonplace in Hyde Park. Chicago has had more laureates than any city in the world—most of them connected to the U of C. Obama charmed the
Herald
's reporter. She noted his “dark brown eyes” and quoted him as saying that working as a community organizer in Chicago had helped him resolve his racial identity crisis.

“I came home to Chicago,” Obama said. “I began to see my identity and my individual struggles were one with the struggles that folks face in Chicago. My identity problems began to mesh once I started working on behalf of something larger than myself. Through this work, I could be angry about the plight of African-Americans without being angry at all white folks.”

Obama tried to get his book reviewed by
N'DIGO
, a magazine for Chicago's upscale blacks. He made weekly phone calls to the publisher, Hermene Hartman, but she turned him down. Obama was a bright, ambitious guy but awfully young to be writing an autobiography, Hartman thought. And the story, with its scenes from Hawaii and Kenya, seemed too exotic for her audience.
N'DIGO
's rejection foreshadowed Obama's later difficulty in convincing Chicago blacks that he was one of their own.

Dreams from My Father
was a modest success, selling around ten thousand copies between the hardcover and a Kodansha International paperback edition that came out a year later. The book did little for Obama's political career. He never mentioned it in his campaign literature, although it did come up in newspaper profiles as a helpful biographical source for reporters. Quite a few people who met Obama after 1995 had no idea he was an author and were surprised when they saw his name on a bookshelf.
Dreams
was available in Chicago bookstores for several years, but it eventually lapsed out of print, until 2004, when the publisher rushed out a new edition to take advantage of Obama's star-making speech at the Democratic National Convention. After that, it sold enough copies to make Obama a millionaire. For a writer, there's no better publicity tour than a presidential campaign.

While Obama struck out with
N'DIGO
, his networking was paying off elsewhere. A guy as skinny as Obama doesn't eat out all the time because he's hungry. In Chicago, he was establishing himself as the city champion of networking, a critical skill when you arrive as a twenty-three-year-old stranger in a place where everyone else started building friendships in grade school.

During his community organizer days, Obama often breakfasted at Mellow Yellow with Stephen Perkins, vice president of the Center for Neighborhood Technology. When Obama went off to Harvard, Perkins thought the social change movement was losing a promising leader. Now that he was back in Chicago, Perkins asked him to join the center's board. The center needed someone with Obama's interest in inner-city economic development. Like any aspiring politician, Obama wanted to build a long résumé of civic involvement. Unfortunately, he didn't stay long enough to make a contribution. Perkins had always admired Obama for being “strategic.” Almost as soon as he joined the board, he was running for the state senate.

Chapter 7

THE FIRST CAMPAIGN

A   S E X   S C A N D A L
created the opening Barack Obama needed to get into politics.

Chicagoans are used to seeing their politicians misbehave, but usually the transgressions involve a lust for money. A secretary of state is found dead in his Springfield hotel room, alone except for $900,000 in kickbacks stuffed into shoeboxes. A congressman uses official funds to buy gift ashtrays and trades in postage for cash, as though he's redeeming green stamps at the supermarket. An alderman shakes down a liquor license applicant for a bribe. The list of hinky officeholders is endless, repetitive, and forgettable.

Representative Mel Reynolds caused such a sensation because his sins were carnal, not financial. Reynolds, a second-term congressman from the South Side, was accused of having sex with a sixteen-year-old girl he'd met during his 1992 run for office. Reynolds had spotted the jail bait while driving around his district and pulled over to chat, even though he was supposed to be politicking and she was too young to vote. Soon after, she joined his campaign as volunteer and mistress. Two years later, the girl confessed to the affair to her next-door neighbor, who happened to be a Chicago police officer. The state's attorney set up a phone-sex sting. While sitting in a prosecutor's office, the girl called Reynolds and told him she couldn't make their tryst because she had to babysit.

“What you gonna wear?” Reynolds asked.

“Well, my peach underwear, like you told me to. I was hoping we could do something really special but I see that's not going to happen, I guess.”

“I was definitely gonna fuck,” Reynolds said.

“Really?”

“Right in my office. I was gonna masturbate too.”

At the panting congressman's urging, the girl spun a story of sex with a lesbian lover. When Reynolds asked if the other woman would be willing to do a threesome, the girl said no—but she knew a fifteen-year-old girl who might. A fifteen-year-old Catholic schoolgirl.

“Did I win the lotto?” Reynolds exclaimed.

There was no fifteen-year-old schoolgirl. But Reynolds's declaration of his lust for teenagers turned into a catchphrase. Jay Leno joked about it on
The Tonight Show
. The case was so salacious it made headlines in Chicago for more than a year. Reynolds won reelection in his heavily Democratic district, but by 1995, he was facing a trial that threatened to cost him his seat in Congress.

Reynolds's downfall was so distressing because he wasn't supposed to be another Chicago pol. His election had represented the same sort of postracial promise and generational change that Obama's would a dozen years later. Born in Mississippi, raised in a housing project, Reynolds had attended Harvard and won a Rhodes Scholarship. After two failed primary runs, he finally unseated Representative Gus Savage, a crude black nationalist who campaigned by reading aloud lists of Reynolds's contributors, lingering over the names of Jews.

Reynolds protested that he was only guilty of phone sex and erotic fantasies, but as his trial approached, a challenger stepped forward. State Senator Alice Palmer announced she would run against Reynolds in the Democratic primary the following March. Palmer's seat was up for reelection in 1996, so, win or lose, she would be leaving the legislature. As a middle-aged woman, Palmer figured to be an appealing candidate against a congressman caught in a sex scandal. She immediately won the support of EMILY's List, which donates to female politicians around the country.

Palmer's state senate district included Hyde Park, so this was Obama's chance.

“If Alice decides she wants to run, I want to run for her state senate seat,” he told his alderman, Toni Preckwinkle.

Obama also discussed his ambitions with Jesse Ruiz, his old law school student. The two were now friends, sharing an annual summer luncheon. In 1995, Ruiz brought a copy of
Dreams from My Father
for Obama to sign.

“You're the only guy I know who wrote a book,” Ruiz said. “Who knows? You might make something of yourself someday.”

That day was now, Obama told Ruiz. He laid out a plan for a political career that would begin in the state senate and culminate with his election to Harold Washington's old job.

“I'm going to need help from you,” Obama said earnestly.

“Barack, Mayor Daley is going to be there forever,” Ruiz said, scoffing. But he agreed to work on Obama's senate campaign. A state senate seat seemed achievable. Ruiz held a small fund-raiser in the apartment of his then-girlfriend (now his wife), raising $1,000.

Around this time, Obama had dinner with Douglas Baird. Now dean of the law school, Baird took Obama to the Park Avenue Café, a fancy downtown restaurant. The dean had woo on his mind. He wanted Obama to become a full-time assistant professor and dedicate himself to law teaching and academic writing.

During the meal, Baird asked Obama about his law school grades. Obama, who took his intellectual image seriously, shot Baird an irritated look. Wasn't a Harvard degree proof enough that he knew the law?

“Douglas,” he said, “I graduated magna.”

So Baird offered him a job.

“Barack, I'd like you to become a full-time academic,” Baird said, “but you have to understand, if you become a full-time academic, you have to seriously commit yourself to academic scholarship. There's no sense getting into something if you don't have relatively clear expectations.”

“Douglas, that's not me,” Obama said.

Obama enjoyed teaching, but he didn't see himself as someone who wrote academic papers or attended conferences where scholars critiqued the works of Richard Posner. It was too far removed from real life. He was going into politics, he told Baird. He was running for the state senate. Obama even asked Baird for a donation. Baird wrote him a check but found it amusing that at one point during the dinner, Obama leaned over and revealed he was wearing an Armani tie. A guy in an Armani tie, Baird thought, asking me for money.

Obama wanted to run for the legislature with Alice Palmer's blessing. But despite his political involvement, Obama had never met his state senator. He had an in, though: Brian Banks, his old colleague from Project Vote!, was managing Palmer's campaign. Obama called him.

“I want to run,” he told Banks. “I want to talk to Alice.”

Banks arranged a meeting at the North Side home of Hal Baron. Baron, who had been Harold Washington's policy director, was chairing Palmer's campaign. At the meeting, Obama told Palmer of his plans.

“Do you have any problem with that?” he asked, wanting assurance, “and will you come back if you lose?”

The second question was especially important to Obama. By the time he met Palmer, Mel Reynolds had been convicted, been imprisoned, and resigned his seat in Congress. That meant Palmer was no longer running in the March 1996 primary. She was running in a special election, scheduled for November 28, 1995, which would give her enough time to refile for the state senate if she lost. And defeat was a real possibility because two better-known challengers had entered the race: Emil Jones Jr., minority leader of the state senate, and Jesse Jackson Jr., the thirty-year-old son and namesake of the civil rights leader. Palmer assured Obama she was all in. It was going to be Congress or bust.

Alice Palmer wasn't a Hyde Parker—she lived in nearby South Shore—but she was perfectly attuned to the neighborhood's character. She had begun her career as an academic, earning a Ph.D. from Northwestern and serving as that university's director of African-American student affairs. Although she was politically active—she founded the Chicago Free South Africa Committee—Palmer didn't get into electoral politics until she was forty-nine, joining in a rebellion against the remnants of the Machine. Her committeeman had supported Jane Byrne for mayor against Harold Washington. After Washington's death, progressives all over the city set out to defeat black and Latino politicians who hadn't had Harold's back. In 1984, Palmer was swept into office as part of the New Ward Committeeman Coalition, a gang of liberals who held regular meetings at a Mexican restaurant and supported pro-Washington candidates for city council.

Seven years later, Palmer was running a nonprofit called Cities in Schools, which brought mentors and money to inner-city students. Richard Newhouse, the long-serving state senator from the Thirteenth District, fell ill and resigned from his seat. It was up to the committeemen to appoint a replacement. They wanted Palmer.

“I'm writing a grant,” she protested. “I'm busy.”

But she was drafted anyway and went to Springfield, where she served as an independent Democrat, helping to ensure that lottery money funded education and holding hearings on universal health care.

Palmer did more than give Obama her blessing and promise to get out of the way. She introduced him as her successor. On September 19, 1995, Obama announced his candidacy before two hundred supporters at the Ramada Inn Lakeshore. Palmer preceded him to the microphone, where she anointed him as a scion of the lakefront liberal movement.

“In this room,” she declared, “Harold Washington announced for mayor. It looks different, but the spirit is still in this room. Barack Obama carries on the tradition of independence in this district, a tradition that continued with me and most recently with Senator Newhouse. His candidacy is a passing of the torch because he's the person that people have embraced and have lifted up as the person they want to represent this district.”

It wasn't just Palmer who signaled that Obama was the independent movement's choice. In attendance were both Hyde Park aldermen, Barbara Holt and Toni Preckwinkle. Also in the crowd was Cook County clerk David Orr, who as an alderman had been one of Washington's few white allies on the city council.

Obama began his first run for office with a lawyer joke. “Politicians are not held to highest esteem these days—they fall somewhere lower than lawyers,” he said, before delivering the message Hyde Parkers wanted to hear: “I want to inspire a renewal of morality in politics. I will work as hard as I can, as long as I can, on your behalf.”

Obama opened a campaign office on Seventy-first Street, far from Hyde Park but close to the center of the district, which reached south into South Shore and west into Englewood, one of the city's poorest, most barren neighborhoods. As his campaign manager, he hired another Project Vote! veteran, Carol Anne Harwell, who had run races for Alderman Sam Burrell, County Clerk David Orr, and Danny Davis, a county commissioner who would later go to Congress. Harwell had been baffled by Obama's interest in the seat.

“Why do you want to do that?” she'd said when Obama told her he planned to run.

“We can make some changes,” he responded. Then he added, “Alice asked me.”

Harwell's job was to transform Obama from a law lecturer to a Chicago politician. Despite Palmer's endorsement, his election was not a sure thing. There were two other candidates: Marc Ewell, the son of a former state representative, and Gha-is Askia, who had the support of Senator Emil Jones and a name as exotic as Obama's. Outside of Hyde Park, Obama was unknown in the district. Not only did he have to get known, he had to overcome the rest of the South Side's suspicion toward uppity U of C types. He decided to spend most of his time campaigning in Englewood. Starting every evening around suppertime, he'd doff his suit coat so he could roll up his sleeves and don the leather jacket he'd worn as a law student.

“Where are you going?” Harwell would ask.

“We're going to circulate some petitions.”

“It's cold, Barack.”

Undaunted, Obama would drive his Saab into the hood. He didn't bother to wear a hat or gloves, even as Chicago sank into winter. That was something else he needed to learn about local politics. After he caught a cold, Harwell scolded him.

“Barack, this is Chicago,” she said. “You have to learn how to dress.”

Obama was a big hit with the little old ladies who answered the doors of Englewood's worn two-flats and decaying houses. They were just as eager as the women of the DCP to mother this skinny young man. He was offered fried chicken sizzling in stovetop pans and invited to sit down and explain where he'd gotten that funny name.

“My father was from Africa,” he explained, and that led to even more conversation, until Obama had spent fifteen minutes to get a single name on his petition. Door-knocking hours were six
P.M.
to eight
P.M.
, and sometimes Obama would leave an apartment house with only three signatures.

“Barack, you can't sit and talk to them,” Harwell lectured. “I'm gonna give you a goal. We're gonna do two sheets.”

As with everything else he'd ever attempted, Obama proved a quick learner. His forays into Englewood also reawakened street smarts he hadn't needed in Hyde Park or at Harvard. One Saturday, as he was walking a precinct with Jesse Ruiz, a group of campaign volunteers ran up to Obama with serious news.

“There's a bunch of thugs coming over and asking us who gave us permission to walk in their neighborhood, and one of them flashed a gun,” a volunteer reported.

Ordinarily, Obama didn't hesitate to approach gangbangers on street corners. But these were his volunteers. And there was a gun involved.

“It's time to go,” he snapped.

Obama got a boost from another old colleague when Bill Ayers and Bernardine Dohrn hosted a Sunday brunch for a dozen Hyde Parkers at their house. Again, Palmer was there and introduced Obama as her chosen successor, touting his bona fides as a community organizer, a Harvard graduate, and a law school teacher.

During the campaign, Obama found time to attend the Million Man March in Washington, D.C. And he was the subject of his first feature-length profile, a flattering, 4,300-word cover story in the
Chicago Reader
, an alternative weekly that served as a house organ for the city's independent movement. Obama told writer Hank DeZutter that he was running for office to empower ordinary citizens, just as he'd done as a community organizer.