Stanback gave the mayor two options for how to proceed. One would be to convey the land to WMI, to whom “the site is probably worth $1 billion,” and in order “to neutralize opposition to lifting the moratorium,” WMI would contribute sufficient funds to the surrounding neighborhoods, just as Mary Ryan’s outreach efforts envisioned. Stanback believed that this could succeed, even with WMI’s “negative image,” and that this was superior to the second option, which would involve the city itself operating a landfill on the O’Brien Locks property. Stanback believed political opposition would be higher to this scenario because it would not include WMI’s contributing to community revitalization projects. “Operating a landfill is not a business the City should enter,” Stanback recommended.
One Saturday, Stanback drove to South Chicago to meet Bruce Orenstein at UNO’s East 91st Street office. Also there that morning was DCP’s Barack Obama, whom Bruce had asked to join them. Stanback described the city’s thinking regarding the landfill and WMI’s proposal, but he also explained that Washington wanted to be sure that WMI’s big gift would not be controlled by the Southeast Side’s traditional power brokers, particularly South Chicago Savings Bank president James A. Fitch, a longtime backer of mayoral rival Ed Vrdolyak and the dominant figure in the four-year-old Southeast Chicago Development Commission (SEDCOM). If a deal could be cut with WMI, the mayor wanted his allies—such as UNO, with whom Washington had worked in close alliance for four years—to take charge of the windfall.
“Barack in particular, his eyes got so bright,” Stanback remembered. “He said, ‘This can be one of the biggest community development coups of all time.’ I said, ‘You’re right,’ ” but UNO at present had no development capacity. “We agreed that nothing was going to happen anytime soon,” Stanback recalled, but “we agreed in principle” that UNO, DCP, and the city would closely coordinate as discussions moved forward. When Fitch then wrote to another Washington aide, budget director Sharon Gist Gilliam, to initiate a discussion of lifting the moratorium to allow for WMI’s use of the O’Brien parcel, Gilliam waited twelve days before sending Fitch a cold, rude reply stating that she had given his letter to Stanback.54
For Obama, the late summer of 1987 was a busy and intense time. Throughout July, his hourly consultations with Greg Galluzzo were more than weekly, but from August forward the two men met only twice monthly, as Greg began having ninety-minute or longer sessions with Johnnie Owens almost weekly. One weekend, Barack met Ann and Maya in New York, where Maya was looking at Barnard College and Ann was visiting friends before returning to Pakistan via London. A rooftop photograph shows Ann and Barack with several of her anthropologist friends, including Tim Jessup, who had first met Barack in Jakarta four years earlier and had seen him again in Brooklyn in 1985 with Genevieve. Barack stayed with Hasan and Raazia Chandoo in Brooklyn Heights, playing basketball nearby with Hasan and walking across the Brooklyn Bridge into Manhattan.
Hasan recalled that “by that time he knows for sure he wants to be a political person,” and Beenu Mahmood, then a lawyer in Sidley & Austin’s New York office, remembered the visit similarly. “By that time he was very clear that he was going into politics” and “it was very clear that law would be the vehicle for getting into politics for him.” Several nights Raazia cooked dinner, but one thing had most definitely changed: by 1987 Barack never again “partied” as he had so many times in 1984 and 1985. Hasan recalled Barack mentioning how brutally cold Chicago winters were and also remembers him describing the time he and Johnnie had to duck behind a car when they heard gunfire nearby in Palmer Park. Raazia, five years younger, found “Barack a little bit arrogant”—just “intellectually arrogant,” Hasan interjected—“so I didn’t want much to do with him.”
Obama was back in Chicago by the end of the second week in August, and he may or may not have seen a prominent headline in the Defender that would have reminded him of an influential relationship from earlier in his life: “Frank Davis Dead at 81.” During Sheila’s midsummer visit home, she told her mother much of what Barack had said to her in recent months, and Shinko Jager in turn recounted Sheila’s comments to Mike Dees, the family’s closest friend, who had met Barack months earlier during the Christmas holiday. Barack’s marriage proposal still loomed, and “if Sheila went with Barack, she would have to follow his lead. He wanted to be president.” Shinko remained opposed to the marriage, “but she never gave a reason,” Mike recounted. “I was against it because I thought they were two ambitious people, and I knew they wanted their own separate careers, and he was talking about being president, which I thought was a little strange” for a twenty-five-year-old community organizer. But there was also something more, something Barack had begun to articulate to Sheila. “There was a problem there,” Mike recalled. “He was concerned if he was going to take the steps to the presidency with a white wife.”
One August Friday, Sheila joined Barack for the trip to Asif’s summer house in Madison. Sheila was “very quiet” and slept in the back of the car most of the drive, but an unusual tension was present. By Saturday morning, the problem broke into the open, and Barack and Sheila kept pretty much to themselves upstairs. But according to someone there that weekend, “it’s the summer … these houses are old. You’d die if you closed windows. Everything is open.” From morning onward “they went back and forth, having sex, screaming yelling, having sex, screaming yelling.” It continued all day. “That whole afternoon they went back and forth between having sex and fighting.”
Others remember “moving around to the other side of the porch just to be able to talk.” It “was a long weekend” and “an incredibly unpleasant one,” one person recalled. “It was so stressed and tense.” Barack tried “to be more social about it,” and “they came down a few times to grab a beer, to eat,” but “then they went back up to scream or fight.” Sheila was “a very sweet person … very mild-mannered,” and “certainly exotic” in her looks, but “shy and withdrawn” that “extremely emotional” weekend.
“They called truces here and there, but it kept popping back up” that Saturday afternoon, as “she screamed and they fought.” Sheila’s voice came through loud and clear: “That’s wrong! That’s wrong! That’s not a reason,” she was heard saying. As the others talked quietly, the explanation of what they were hearing was shared: Barack’s political destiny meant that he and Sheila could not have a long-term future together, no matter how deeply they loved each other. But she refused to accept his rationale: “the fact that it was her race.” It was clear—audibly clear—that “she was unbelievably in love with him,” that “the sex for her was the way to bring it back.” Barack “was very drawn to her, they were very close,” yet he felt trapped between the woman he loved and the destiny he knew was his. According to one friend, Barack “wasn’t black enough to pull that off and to rise up” with a white wife.
Sunday afternoon Barack drove them south to Chicago, with Sheila again napping in the back seat. “Thank god it’s a crappy car that made a lot of noise!” A quarter century later, Sheila had almost no recollection of going with Barack to Madison, but she unhesitatingly characterized their relationship as “a very tumultuous love affair.” No matter how others saw Obama, “the Barack I knew was not emotionally detached, in control, and cool,” she stressed. Instead, Barack was “a very passionate, sentimental” and “deeply emotional person,” indeed “the most overwhelmingly passionate and caring person I ever knew.”
In Barack’s workday world, Cathy Askew, the white single mother of two half-black daughters, witnessed most starkly Barack’s newly articulated racial identity. With a new school year about to begin, Cathy told Barack about what she considered a perplexing and offensive racial conundrum: although the Chicago Board of Health said her daughters were black, their school in West Pullman wanted to count them as white. Cathy rejected this binary view of racial identity—“50-50 is a good term”—and expected biracial Barack to agree. She was astounded when he rejected any middle ground, especially since he had spent most of his childhood in a predominantly “hapa” world. But he did. “He said, ‘Well, there comes a time when you have to pick a side, you have to choose a side,’ ” Cathy remembered him saying. And Barack repeated it: “You have to choose.”
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