After an explosion in the Weathermen’s Greenwich Village bomb-making laboratory killed three of their fellow Weathermen (including Ayers’s girlfriend at the time, Diana Oughton) and virtually destroyed the neighboring town house owned by Dustin Hoffman, Ayers and Dohrn went underground. In 1973 charges against them were dismissed due to prosecutorial misconduct, but Dohrn remained a fugitive until she finally turned herself in to police in 1980.
Ayers made no apologies for his terrorist past, and in the 1990s still described himself as “a radical, Leftist, small ‘c’ communist…. The ethics of communism still appeal to me. I don’t like Lenin as much as the early Marx.”
Ayers’s radical past didn’t seem to bother Chicago’s civic leaders, many of whom worked with him on education reform. He worked particularly closely with Mayor Richard M. Daley on reshaping the city’s school programs—an effort that also brought him into contact with one of Daley’s assistants at the time, Michelle Obama.
What did interest Barack were Ayers’s proven abilities as a writer. Unlike Barack, Ayers had written and cowritten scores of articles and treatises, as well as several nonfiction books beginning with Education: An American Problem in 1968. But it was the tone Ayers had set in his latest book—To Teach (1993)—that Barack hoped to emulate.
The tale of a maverick teacher who takes her students onto the streets of New York to teach them firsthand about history, culture, and survival, To Teach was written in a fluid, novelistic style. Barack asked for Ayers’s input, and Ayers, who like so many in his circle was greatly impressed by the charismatic young activist, obliged.
To flesh out his family history, Barack had also taped interviews with Toot, Gramps, Ann, Maya, and his Kenyan relatives. These oral histories, along with his partial manuscript and a trunkload of notes, were given to Ayers. “Everyone knew they were friends and that they worked on various projects together,” another Hyde Park neighbor pointed out. “It was no secret. Why would it be? People liked them both.”
In the end, Ayers’s contribution to Barack’s Dreams from My Father would be significant—so much so that the book’s language, oddly specific references, literary devices, and themes would bear a jarring similarity to Ayers’s own writings. Even the caveat at the beginning of Dreams, in which Barack points out that he uses invented dialogue, embellished facts, composite characters, inaccurate chronology, and pseudonyms to create an “approximation” of reality, resembles Ayers’s defense of the inaccuracies in his memoir Fugitive Days. In the foreword to his book, Ayers states that the book is merely a collection of his personal memories and “impressions.”
“There was a good deal of literary back-scratching going on in Hyde Park,” said writer Jack Cashill, who noted that a mutual friend of Barack and Ayers, Rashid Khalidi, thanked Ayers for helping him with his book Resurrecting Empire. Ayers, explained Cashill, “provided an informal editing service for like-minded friends in the neighborhood.”
Certainly none of these authors hesitated to acknowledge their admiration for one another at the time. In his 1997 book, A Kind and Just Parent, Ayers would cite the “writer” Barack Obama (along with Muhammad Ali and Louis Farrakhan) as one of the celebrities living in his neighborhood. In turn, Barack would write a glowing review of that same book for the Chicago Tribune, and Michelle would host a panel discussion on the book at the University of Chicago, with Ayers and her husband as the principal speakers.
Thanks to help from the veteran writer Ayers, Barack would be able to submit a manuscript to his editors at Times Books. With some minor cuts and polishing, the book would be on track for publication in the early summer of 1995. In the meantime, he began showing the rough draft to a chosen few relatives.
Toot, for one, was miffed at his portrayal of Gramps as a bitter man, and of the tensions that arose in the house when she became the principal breadwinner. And she didn’t like the profanity used in the book, particularly one word that described a part of the female anatomy. “It probably made her a little nervous, having the family written about,” Maya said of their grandmother, “just because you don’t do that in Kansas.”
Toot was also worried about passages where Barry admitted to being a regular user of pot and an occasional user of cocaine in his youth. It was a concern shared by Michelle. “That stuff isn’t going to sit well with the ladies at church,” she warned him—the very women, she pointed out, that he would need once he decided to run for Governor or the U.S. Senate.
Barack disagreed, and so did Jeremiah Wright. In recent years, Wright had become increasingly strident in his rhetoric—among other things, praising the likes of Louis Farrakhan, Fidel Castro, and Muammar Gadhafi, and attacking Washington for allegedly starting the AIDS epidemic as part of a vast conspiracy to annihilate the world’s black population. A number of church members—most notably Oprah Winfrey—left the church. Winfrey would later explain that there were a number of reasons for this, including a dissatisfaction with organized religion in general. Still, Wright’s increasingly militant statements were a factor. “Oprah is a businesswoman, first and foremost,” one longtime friend told Newsweek. “She’s always been aware that her audience is very mainstream, and doing anything to offend them just wouldn’t be smart.”
Barack, who heard such messages delivered from Wright’s pulpit scores of times over the years, apparently did not share Oprah’s misgivings. The reverend remained the Obamas’ closest and most trusted spiritual adviser. Wright, who had always been candid about his own teenage arrest record, urged Barack to share the details of his marijuana and cocaine use in the book. Not only was it an evocative illustration of Barack’s own “redemption,” Wright told him, but it would speak directly to young men in the black community who had struggled or were struggling with drugs.
Moreover, Barack, who now described Wright as “a father figure” to him, had shared his political aspirations with the reverend in detail. Wright reminded him that, despite Barack’s contributions to the black community, there were those who remained wary of him. While Trinity United’s congregation was more affluent and sophisticated than most, many people Barack encountered on the South Side still found the eager young activist too exotic (raised in Hawaii and Indonesia), too well educated (Columbia, Harvard), and too white (raised by his Kansan grandparents, his speech had neither the cadence nor the rich flavor of Chicago’s African American community).
Barack had long been concerned that he lacked “street cred,” and had already explained to Michelle that his book offered the fastest and most effective way to remedy the situation. Now that Wright agreed, Michelle dropped her opposition. “Barack loved and respected Reverend Wright,” said a fellow church member, “but not as much as Michelle. She had grown up going to church, and made that kind of attachment to her pastor. Michelle was in total awe of Reverend Wright.”
Barack also sent the manuscript to his mother in Hawaii. The book’s focus on Barack’s father, who had abandoned Barack and Ann to return to Africa, surprised her. It was Ann, after all, who—along with Toot and Gramps—had raised Barack and shaped his values. But Ann shrugged it off. “She never complained about it,” her friend Nancy Peluso said. “She just said it was something he had to work out.”
Around this time, Ann returned to Indonesia to do more fieldwork and to reconnect with several old friends. She was dining in the Jakarta home of one of them, economist Richard Patten, when she doubled over with a sharp stabbing pain in her stomach. The next day she went to a local doctor, who diagnosed her with indigestion, gave her an over-the-counter remedy, and sent her on her way.
The pains in Ann’s abdomen persisted, however, and when she returned to Hawaii three months later she visited a doctor again. This time, she was told she had advanced uterine and ovarian cancer.
Understandably, Barack was devastated by the news. That Christmas, he and Michelle flew out to Hawaii as they always did to spend the holiday with Barack’s family. Chemotherapy had caused Ann’s hair to begin falling out, but the pr
ognosis was hopeful. What really concerned Ann at the time was the possibility that her insurance might run out, leaving her unable to pay for her cancer treatments. “At a time when she should have been focused on getting well,” he later said, “my mother was in a hospital bed arguing with her insurance company because they refused to cover her treatment on the grounds that she had a ‘preexisting condition.’”
Barack returned to Chicago more determined than ever to run for office. He went to his friend Abner Mikva and asked him to put out feelers to see if any office might be opening up. “He couldn’t wait,” Mikva said, “to get into the ring.”
He wouldn’t have to wait long. In early 1995, Illinois Congressman Mel Reynolds was facing charges of having sex with an underage campaign worker. In August, Reynolds would be convicted and sentenced to two years in prison (later he would be sentenced to an additional six and a half years for wire and bank fraud). Reynolds finally resigned his seat on October 1. But in the meantime, there was a frantic scramble to replace him. One of those most interested in Reynolds’s job was fifty-five-year-old African American State Senator Alice Palmer.
This was precisely the opening Barack had been searching for. He had actually paid a visit to his alderman, Toni Preckwinkle, to broach the subject in January of 1995. “If Alice decides she wants to run for Mel Reynolds’s seat,” Barack told Preckwinkle, “I want to run for her State Senate seat.”
His first run for office aside, 1995 would turn out to be an eventful year for the Obamas. On June 22, Barack was officially named chairman of the Chicago Annenberg Challenge—an Annenberg Foundation—funded grant that was the brainchild of Barack’s friend and neighbor Bill Ayers. The Challenge, aimed at promoting reforms in the public school system, would dole out $49.2 million to various experimental projects—including a “Peace School” where the curriculum centered on a United Nations theme—before shutting down in 2003 because, said the foundation’s final report, it had “little impact on school improvement and student outcomes.”
Five days after Barack’s appointment to head the Annenberg Challenge, Alice Palmer announced she was running for Congress and soon made it clear that she backed Barack to succeed her in Springfield. Not long after, Bill Ayers and Bernadette Dohrn hosted a small gathering for Palmer in the living room of their Hyde Park home. Barack was there as well, and while Ayers did not technically launch his political career as would later be widely suggested, he was most likely the first to introduce Barack as a candidate.
Then, on July 18, 1995, Dreams from My Father was published to generally positive reviews. Barack embarked on a ten-day national book tour, and although in this first incarnation Dreams would sell only ten thousand copies, it added considerably to the author’s cachet among Chicagoans.
One of several book parties honoring the novice author was thrown by Valerie Jarrett, who packed her elegant art deco-designed co-op in the Kenwood district of Hyde Park with some of Chicago’s wealthiest and most influential citizens. Coincidentally, it was the same week Mel Reynolds was convicted in his sexual assault case. Alice Palmer had already announced her intention to run for Reynolds’s soon-to-be-vacated seat, and Jarrett’s book party was abuzz with gossip about Barack’s impending run to fill her seat.
“Michelle was there,” remembered one guest, “working the room like a pro while he sat there autographing books.” Her mood changed noticeably, however, when talk of a possible State Senate run came up. “Everyone was buzzing about it, but,” said the guest, “Michelle was clearly not enthusiastic.”
Indeed, Michelle confided to one longtime friend that the subject had been the source of heated arguments between them. “It’s beneath you, Barack,” she told him. “It’s too small-time. What can you possibly accomplish in Springfield?”
But Barack persisted, and Michelle acquiesced. “I married you because you’re cute and you’re smart,” she said. “But this is the dumbest thing you could have ever asked me to do.”
On September 19, more than two hundred supporters showed up at the Ramada Inn Lakeshore in Hyde Park-Kenwood to hear Barack announce his candidacy in the same room where Harold Washington had announced his candidacy for mayor thirteen years earlier. “Barack Obama carries on the tradition of independence in this district,” Palmer said when she introduced him to the standing-room-only crowd. “His candidacy is a passing of the torch.”
In addition to setting him up with several of her key precinct operatives, Palmer went to her longtime supporters and asked if they would host a series of coffees to introduce Barack to voters. Over the course of the next six months, there would be as many as four per week.
One of the first of these meet-and-greet events was hosted by Rabbi Arnold Jacob Wolf. “Someday you are going to be Vice President of the United States,” Wolf told him.
Barack laughed. “Why not President?” he asked.
Another couple who hosted one of these coffees had no such reservations about Barack’s prospects. “This guy,” Martha Ackerman said to her husband, Sam, “could be the first African American President of the United States.”
It was during this period that, according to Barack, his relationship with controversial Syrian-born developer Tony Rezko “deepened.” Rezko had pushed for legislation to give hefty tax credits to real estate developers like himself who were willing to build low-income housing in Chicago’s run-down neighborhoods. Rezko hired Davis, Miner to represent his interests, and in the process became friendly with Barack.
While he had turned down Rezko’s frequent entreaties to go to work for him as far back as his days on the Harvard Law Review, Barack did consult him on his political future. He also relied on Rezko for financial support; the developer would become his largest single contributor, paying for a considerable chunk of Barack’s State Senate campaign.
One of Tony Rezko’s biggest boosters was Michelle, who had met him during her stint as Mayor Richard M. Daley’s economic development coordinator. The Obamas soon began socializing with Rezko, dining at his Wilmette, Illinois, mansion, and even visiting his sprawling vacation home in Lake Geneva, Wisconsin. “Michelle was impressed with the Rezkos and their devotion to her husband, and she clearly enjoyed their company,” said a Rezko business associate who dined with both couples on several occasions. “Michelle encouraged Barack to cultivate the Rezkos. I think she liked them even more than he did.”
With his March 1996 primary still five months away, Michelle pressed Barack to take time out to visit his desperately ill mother in Hawaii. Toot and Maya had been keeping Barack apprised of her worsening condition, but Ann kept insisting she was doing fine and responding to treatment. There was no reason, she said, for her son to interrupt his campaign to visit her.
Michelle wasn’t buying it. “Dad always said he was feeling great no matter how bad he really felt,” Michelle reminded Barack. That was precisely what he said when he went out the door to work that final morning. Michelle still regretted the fact that no family member was with her father when he passed away, and she did not want Barack saddled with the same feelings of remorse.
“I think you ought to take the time to go out and see your mother,” Michelle told her husband, trying to downplay the fact that it might well be the last time. “You can surprise her. She’ll be thrilled.”
Whether or not he was in denial about the gravity of his mother’s condition—she had been told at the time of her diagnosis that she had only a slim chance of survival—or actually believed Ann’s fervent claims that she was responding to treatment, Barack put off visiting his mother.
Instead, Jeremiah Wright had persuaded Michelle to let Barack accompany him to Nation of Islam leader Louis Farrakhan’s Million Man March in Washington on October 16, 1995. As soon as he returned, Barack approached the alternative newsweekly the Chicago Reader and offered to share his impressions of the event.
“Historically,” he told the Reader, African Americans have turned “towards Black Nationalism whenever they have a sense, as we do no
w, that the mainstream has rebuffed us, and that white Americans couldn’t care less about the profound problems African Americans are facing. What I saw,” he continued, “was a powerful demonstration of an impulse and need for African American men to come together to recognize each other and affirm our rightful place in society.”
Less than three weeks later, on November 7, 1995, Barack was back in Chicago working on his campaign when news came that Ann had died. She was fifty-two. As Michelle had predicted, he was overcome with guilt. “I should have been there,” he told her. “I should have been there…” Maya and Toot tried to reassure him that the end had come suddenly, unexpectedly—that they had all believed there would be time for him to say good-bye. But Barack would never forgive himself. “The single greatest regret of my life,” he would later say, “was not being there when my mother died.”
Barack and Michelle flew to Hawaii and, along with Toot and Maya, scattered Ann’s ashes over the Pacific. “My mother was the sweetest woman I’ve ever known,” he would say. “Everything I am, I am because of her.”
When Michelle and Barack returned to Chicago, they brought with them some of the treasures his adventurous mother had collected over the years—including her childhood arrowhead collection from Kansas and two trunks crammed with Indonesian batiks. Ann’s friends would also say that something of her lived on in her son. “When Barack smiles,” said Nancy Peluso, a pal from her days in Indonesia, “there’s just a certain Ann look. He lights up in a particular way that she did. There is this thing in his eyes.”
Barack would need all the optimism he could muster. As the primary election for Mel Reynolds’s Second Congressional District seat approached, it was clear to everyone that Alice Palmer was going to go down to defeat. Still upset by the loss of his mother, Barack met with a group of veteran black leaders who asked him to release Palmer from her promise not to run for reelection to the State Senate.
“We want you to step aside,” one of the men said, “like other African Americans have done—for the sake of unity.”
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